CHAPTER THIRTEEN

A Challenger Emerges

Inside the White House, Biden’s relationship with Obama only grew. The two men frequently had lunch, and Obama came to value Biden’s advice, especially in areas of foreign policy. Biden had argued strenuously against a troop surge in Afghanistan, staking out the most liberal position among Obama’s foreign policy advisors—in part out of principle, but also to provide the president with a real alternative to Clinton, Gates, and the hawks among Obama’s counselors.

But Biden’s relationship with Obama’s chief political aides wasn’t as smooth. He had not gotten along well with David Plouffe, which actually was a real point of personal frustration for the vice president. So after Plouffe didn’t come to the White House at the start of the term, Biden ingratiated himself with the other David, Axelrod. He was much closer to Biden’s age than was Obama, and he respected one aspect of Biden’s talents. While Axelrod loved Obama’s ability to wow a crowd, he thought of Biden as one of the more gifted person-to-person politicians he had ever seen.

Still, Biden’s political instincts were decidedly old-school. At one point, in the months leading up to the midterm elections, Biden and Bill Clinton had persuaded each other that the White House’s political troubles were exacerbated by its inability to convince the American public of the value of health care reform. The two men sketched plans—going so far as to write the text—for a brochure they wanted the Democratic National Committee to print. Tens of millions of copies would be dropped off at voters’ homes, and the communications problem would be solved. Axelrod, Obama’s political advisors, and even some of Biden’s top aides thought the idea was decades out-of-date in an age of e-mail; the brochures were never printed.

The transition to full-on campaign mode meant West Wing staff changes, the two biggest being the departures of David Axelrod and Robert Gibbs. Although the Axelrod exit was part of a larger plan to prep for the re-election effort, Gibbs’s decision to leave was a bit more sudden. While he had helped feed the chatter that he would like a break from serving as the president’s chief spokesman (it entailed lots of time behind a podium answering reporters’ questions), Gibbs didn’t necessarily want to exit the White House altogether. Ideally, he was hoping to stay on in a more behind-the-scenes role as a senior advisor, even sharing some of the political duties with Plouffe. But Gibbs had clashed with a few key White House insiders, including Jarrett. And those clashes with Jarrett usually had something to do with the First Lady.

Gibbs was not always very diplomatic when talking to or about Jarrett, and he didn’t do his best to hide his disdain for her. It was a tension that was tolerated for a while, even by the president. Gibbs was among the “guy’s guys” the president liked to surround himself with, especially when on the road. But Gibbs also had a habit of being too cold and calculating about what he thought. When the First Lady was planning a girls’ vacation in Spain while the president was leading a country that still felt it was in a recession, it fell to Gibbs to beg the president to talk her out of the trip. Obama understood how bad the jaunt would look politically, but he was not about to tell the First Lady no. Whatever deal the First Couple had cut—which essentially meant prioritizing Obama’s career over Michelle’s—was tough enough that the president didn’t think he should ask her to cancel. Gibbs’s playing bad guy got back to the First Lady, and she in turn would vent her displeasure with him to Jarrett. With no obvious other place for Gibbs in the West Wing, he chose not to push to stay. He could have, but there wasn’t a lot of enthusiasm for it, and he didn’t need to stay that badly. Thus he began to play a different role in the campaign.

Axelrod’s exit was less abrupt. For one thing he was tired of living in an apartment in Washington, and with the campaign gearing up in Chicago he had more than the excuse of his family to move back.

When Axelrod left the White House after the midterm elections, he had been replaced by Plouffe. On the face of it, the newcomer (so to speak) and Biden should have had plenty to talk about; both came from Delaware, both had graduated from the University of Delaware, and both were fiercely loyal to and protective of Barack Obama. But the two men clashed. Plouffe saw Biden as a dinosaur, a generation sure to be the last of its political kind. For his part, the vice president saw disloyalty in Plouffe; here, after all, was a Delaware native who chose to work for Obama, and everyone in Delaware Democratic politics was a Biden guy. Except David Plouffe. The tension went back further: in 1988, when Biden ran for president the first time, Plouffe was working for a rival campaign, for Dick Gephardt, the Missouri Democrat.

Biden’s relationship with Axelrod was much better, partly because they had similar outlooks on politics, and partly because their personalities matched—both were outgoing, prone to chatter in the cloakroom and newsroom, respectively. Privately, Biden compared Plouffe with Obama: both are cool under fire to the point of being cold, both loathe to be ruffled, both prefer the counsel of a handful of allies and friends.

Still, Plouffe needed Biden. The assets the vice president brought to the White House—foreign policy expertise, deep relations with Congress—were great from a policy perspective, but Plouffe’s single-minded focus, almost from the day he moved into his West Wing office, was to re-elect Barack Obama. And Biden had credibility with some voters that Obama did not, particularly seniors in the Rust Belt and Florida.

Plouffe, Axelrod, and Obama’s political advisors understood that the electorate that had voted Obama into office had fundamentally changed. Minorities had become such a significant proportion of the electorate that Democrats (whose coalition is much more racially diverse than Republicans’) could rely on them to offset the white voters who more reliably voted for the GOP candidate. Jimmy Carter needed 47 percent of the white vote to beat Gerald Ford in 1976; Bill Clinton and Ross Perot together accounted for 59 percent of the white vote in 1992, when Clinton won the White House. Democrats lost in 2000 and 2004, when they received 42 percent and 41 percent of the white vote, respectively. But, underscoring the rapid growth of minority voters since then, Obama had won decisively in 2008 when he took just 43 percent of the white vote. And while Plouffe thought they could win in 2012 with less than 40 percent of that vote, he didn’t believe he had much margin for error.

There wasn’t enough minority support to allow the White House to give up on white voters entirely. And as Obama’s approval ratings fell, it was those former fans—whites, both men and women, usually with less education, living in the industrial Midwest (or former midwesterners living in Florida)—whose attitudes soured most.

Biden was part of the answer, a surrogate who could help slow the bleeding of white votes, or so he hoped.1 He had an ability to connect with white working-class voters that Obama simply lacked. So in November 2011, a year before Election Day, the Obama campaign announced that it would dispatch Biden to several key states—Pennsylvania and Ohio, where salvaging as many of those white votes as possible was key to victory, and Florida, where Jewish voters held the secret to improving the president’s white support. Biden would also make it a point to connect with union officials in key states, in hopes of maximizing votes from a traditional Democratic power base. Republican analyst Dan Schnur put it best in a comment to USA Today: “Obama provides the speeches, and Biden provides the blue-collar subtitles.”2

As the fall of 2011 wore on and Messina and Plouffe were openly nervous about Obama’s chances, the man they considered his likely opponent was struggling.

The Republican Party has something of a tradition of nominating presidential candidates who have run before—in fact, whoever came in second last time around. John McCain, Bob Dole, George Herbert Walker Bush, even Ronald Reagan had all run and lost before they came back to win their party’s nomination the next time they had a clean shot. After 2008, when McCain had outlasted a better-funded, better-staffed Mitt Romney, it became clear that Romney was next in line.

If they had placed bets, even as early as 2008, Obama’s advisors would have staked their fortunes on facing Romney four years down the road. And it was obvious that they had a wary eye on the likely Republican nominee even before Obama took the oath of office in 2009.

Given the small circle of elite politicians, it is not uncommon for candidates to have relationships with their future opponents. In a quirk that demonstrated just how unusual both Obama’s and Romney’s journeys had been, before Obama’s inauguration the two had spoken directly to each other only a few times, and those exchanges had usually been a matter of seconds, done for cameras and not as camaraderie. The first time was in 2004, before Obama was even sworn in as a senator, when he and Romney were guest speakers at the Gridiron dinner (the same dinner he would shirk a few years later). Most of his and Romney’s barbs were aimed at the same person, the fast-rising star, Obama. Obama was all self-deprecation: “It’s like I was shot out of a cannon. I am so overexposed, I make Paris Hilton look like a recluse. After all the attention—People magazine, GQ, Vanity Fair, Letterman—I figure there’s nowhere to go from here but down. So tonight, I announce my retirement from the United States Senate. I had a good run.”

Romney’s poke at Obama was on the same topic. He said Obama was “not seeking the limelight and he’s said that again and again and again on Letterman, on Leno, on Meet the Press…” And so it went.3

Their second ever conversation came in December 2008, when the president-elect called Romney after Romney’s wife had been diagnosed with breast cancer. Obama asked Romney to convey his best wishes for Ann’s speedy recovery.4 Otherwise their interactions had been the standard pre- and postdebate handshakes.

One of those handshakes had been during the 2008 campaign, at a joint Democratic-Republican debate, so Plouffe and the others had seen the potential Republican nominee onstage with their guy, holding his own. The Romney of 2008 was a very aggressive debater, even more so than he would eventually be in 2012. In a sign of respect for, even trepidation about, a future rival, the Obama White House would let slip more than a few times that they had Romney on the brain. Obama mentioned Romney at a ceremony awarding Edward Brooke, the last Republican senator from Massachusetts, a Congressional Gold Medal, in October 2009.5 And press secretary Robert Gibbs brought up Romney’s name for the first time in a daily briefing in March 2010, more than a year before Romney officially kicked off his presidential campaign.6

Perhaps most conveniently, the White House went to great lengths to compare its signature first-term accomplishment—reforming the nation’s health care system—to Romney’s greatest legislative accomplishment as Massachusetts governor, especially once the White House decided to go the mandate route. It even used some of the same advisors who had helped craft “RomneyCare” to come up with a version that would fit on the national stage—a fact the Obama White House enjoyed leaking and then touting.

Indeed, the image of Romney signing into law a bill actually known as Commonwealth Care at Boston’s famed Faneuil Hall, with Ted Kennedy beaming as he looked over Romney’s shoulder, gave the Obama White House a shield, an opportunity to point to a Republican governor’s signature as evidence that its law would work on a national level and that it wasn’t some wacky left-wing, socialistic idea. The image gave the Romney campaign constant headaches; as health care reform took on new and sinister meanings for Republican primary voters in 2012, Romney’s rivals used the White House’s association with Commonwealth Care to bludgeon the front-runner from the moment he jumped into the race. Before dropping out, Tim Pawlenty dubbed health care reform “ObomneyCare.” It was a ham-handed and clunky phrase, but in some GOP corners, it stuck.

If Obama’s opponents would fault him for turning his eyes to the White House mere months after arriving in the Senate, Romney’s rivals would note the same single-minded focus. Elected as a moderate governor of bright-blue Massachusetts in 2002, Romney had once declared himself to the left of Ted Kennedy on gay rights issues. But since 2005, with an uphill re-election fight looming, Romney had carefully laid the groundwork for his evolution from Massachusetts moderate to mainstream national conservative. He opted against running for a second term, which he might have lost, thereby jeopardizing his presidential prospects; he became chairman of the Republican Governors Association, which gave him access to big donors who could fund his national ambitions; and he took a series of stands decidedly to the right of his previous positions. In a dramatic editorial published in the Boston Globe, Romney declared himself opposed to abortion, a conclusion he said he’d come to after conversations with religious figures.7

Romney had bragged about his accomplishments on health care during his 2008 campaign for president. But in the intervening years, the GOP’s base had become ideologically more rigid, not just anti-Obama but, in the inarticulate words Romney once awkwardly used, “severely conservative.” The Republican primary electorate had always been conservative, but now the establishment in Washington was feeling the need to appease this more vocal wing of the party. A fast-growing conservative news media was demanding strict adherence to a more conservative ideology, and they were leery of conservative newcomers. And although Romney veered to the right before there was a Tea Party, it wasn’t soon enough for many. And then there was health care. Congressional Republicans, talk radio hosts, and tens of thousands of sign-waving, red-faced conservative activists denounced Obama’s health care plan as government run amok, radical overreach that threatened their economic well-being, their way of life, and the Republic itself. Suddenly, the story went, Obama was forcing his will on millions of Americans with something called a mandate—a mandate that also happened to be at the heart of Romney’s health care plan from a few years earlier.

The mandate was a requirement that everyone buy some kind of insurance, or pay a penalty. It had its roots circa 1993 at the Heritage Foundation, a conservative Washington think tank where a top health care policy expert had crafted a requirement that individuals take responsibility for their own well-being rather than foist the costs of emergency room visits on the taxpayer. That mandate became a central tenet in the health care plan that Senate Republicans, led by Rhode Island’s John Chafee, had offered as an alternative to Hillary Clinton’s reform efforts in 1993 and 1994. In hindsight, one wonders whether the GOP’s decision to rally around this mandate alternative to “HillaryCare” in the 1990s was a genuine effort, or simply the easiest way at the time to combat Clinton. Still, Romney had adopted that conservative position of the 1990s into his own plan in 2005 and then boasted of his achievements. But the Republican messaging of the intervening years put Romney, and some of his biggest supporters, in a difficult spot. In a sign of just how much things had changed, Jim DeMint, the conservative Republican from South Carolina who became a vanguard of the Tea Party movement, backed Romney in 2008 in part because of his health care plan. In 2012, DeMint held back on endorsing Romney, citing concerns over the same health care plan. The positive that once spoke to Romney’s bipartisan, solutions-oriented approach to governing had turned into an albatross.

Romney’s team was so concerned about the prospect that their candidate’s record on health care could derail his presidential ambitions that they sent their man into early damage control mode. A few weeks before formally announcing his candidacy, Romney gave a detailed presentation on health care at the University of Michigan. In an attempt to thread a delicate needle, Romney, using the sort of PowerPoint slides that had been a staple of his presentations as a business consultant, made clear he would not disown Commonwealth Care as a whole, though conservatives were begging him to do so. But he drew a crucial distinction: although Commonwealth Care had been right for Massachusetts at the time, he said, it shouldn’t be used as a national model. It was a potentially clever appeal to states’ rights, the last resort every Republican who is at odds with the national party uses to defend certain un-conservative positions. But it wasn’t an easy argument to make, and it wasn’t one that any of his opponents—or primary voters—ever let go.

Throughout the yearlong primary process, Romney remained a sort of fragile front-runner. The preprimary, the months before any actual votes were cast, became a sort of whack-a-mole game for the Romney campaign. With the conservative electorate constantly in search of an alternative to the man they saw as a Massachusetts moderate, a rival would have a strong debate, or deliver a well-received speech, or win a straw poll, and suddenly his numbers would soar. Some would gain traction in the polls without even announcing, including Donald Trump. The metrics—the amount of money Romney had, the number of top-tier endorsers and surrogates, the quality and volume of campaign strategists—suggested that Romney was unbeatable in the primary. But polling data disagreed; throughout 2011, he consistently found himself running behind other candidates. On any given day during the Republican primaries, it was easy to think that both of the following sentences were true: it’s impossible to see how Romney isn’t the nominee, and it’s nearly impossible to see how he gets it.

But the anti-Romneys peaked and failed with incredible regularity, a host of Icaruses flying too close to the sun before plunging into political oblivion. Trump was the first to fall, after he went on his bizarre birtherism wild-goose chase. Herman Cain, the radio host and eccentric former head of Godfather’s Pizza, enjoyed a moment at the top after his simple tax plan (9-9-9, short for a 9 percent flat income tax, 9 percent flat corporate tax, and 9 percent national sales tax) and inspiring story captured conservative imaginations. But reports that Cain had been accused of improper behavior toward a number of women while serving as head of the National Restaurant Association, although endearing him to some conservatives who suddenly had another reason to hate the liberal media, effectively ended his campaign. Michele Bachmann, the outlandishly overstated congresswoman whose conservatism made even her Republican-heavy Minnesota district vulnerable to Democratic takeover, became the first woman to win a straw poll held by the Iowa Republican Party, a touchstone event that serves as an early indicator of a candidate’s organizational skills. Her repeated gaffes, however, including one confusing Concord, Massachusetts, where the first shots of the Revolutionary War were fired, with Concord, New Hampshire, helped bring her campaign to an early conclusion.*

Tim Pawlenty, who had hired top-tier advisors and introduced himself to primary voters with splashy videos that would have made over-the-top action director Michael Bay envious, had been the anti-Romney who looked best on paper, but he fared worst on the trail. He never caught fire with the grass roots, perhaps because Minnesota Nice—his worst affliction—didn’t appeal either to Republican primary voters desperate for blood or archconservatives looking for someone capable of taking Romney down a peg or two. (Pawlenty dropped out a day after Bachmann, his fellow Minnesotan, beat him in the Iowa straw poll.) Later, many Republican operatives (including Romney’s folks) would wonder what might have happened had Pawlenty stayed in for a while, languished, and taken off at a later date, say closer to Iowa.

Rick Perry, the governor of Texas, vaulted highest and fell fastest. There could be no questioning Perry’s conservative values; he had been an early champion of Tea Party activists who invoked the Tenth Amendment guaranteeing states’ rights, and he even hinted that secession was a possibility if health care reform were forced upon unwilling outposts like the Lone Star State.

Perry, unlike other understaffed Republican candidates, quickly assembled an A-list staff and big-name backers, giving those looking for a Romney alternative hope that one had finally emerged. He raised $17 million8 in his first few weeks in the race, easily outpacing Romney and threatening to take control of the contest. But Perry had been reluctant to enter the race in the first place, at least until he had surgery on his back, which had plagued him for years. He had the surgery in July 2011, a month before jumping in, but the pain persisted; in debates, other candidates proved to be faster on their feet, and Perry’s advisors privately conceded that he was in too much agony to be in top form.

If health care was a political hot potato, Perry grabbed hold of a virtual molten rock: illegal immigration—the lone issue on which he diverged from 2012 conservative orthodoxy. And thereafter his poll numbers began to fall. At one debate, he defended a Texas law that allowed the sons and daughters of illegal immigrants to attend state universities at in-state costs. Romney pounced—a decision some in Boston knew he’d regret if he became the nominee, but (one campaign at a time) he had to find a way to outflank Perry. In fact, immigration was the one issue on which Romney had been more conservative than McCain in 2008 (and it nearly allowed him to upset the Arizonan then), and it was the only issue on which he was more conservative than Perry. And Romney went at the issue—hard. The Texan never really recovered from the onslaught. A few weeks later, at a make-or-break debate in Michigan, he famously pledged to shut down three executive branch departments, then forgot the name of the third department, and his chances to consolidate the anti-Romney forces had all but collapsed.

Two other whack-a-moles remained: Rick Santorum, the former Pennsylvania senator and Christian conservative icon who had lost his seat in the 2006 Democratic wave, and Newt Gingrich, the former House Speaker who had essentially been forced to resign after his party failed to pick up seats in the 1998 midterm elections.

Both seemed long shots for the anti-Romney mantle. Santorum had been walloped in a swing state by Democrat Bob Casey, hardly the résumé of someone claiming viability in a general election against a sitting president. Santorum had little money, and on virtually every debate stage he had been relegated to the wings, a position reserved for the candidate with the lowest support in the polls. (Throughout the fall of 2011, he would be lucky if a survey showed him winning more than 1 percent of likely Republican primary voters.) But he persisted nonetheless, motivated more by the idea of redemption for 2006 than by actually winning.

Gingrich had the loyal backing of established, skilled operatives that Santorum lacked, but those operatives had spent the better parts of their careers deeply involved in Newt, Inc., the series of nonprofit groups and think tanks Gingrich used to churn out his policy positions. If Santorum wanted to be the heart of the conservative movement, Gingrich wanted to be its brain. His past included two messy divorces and enough political baggage to weigh on the minds of primary voters; an advertisement run by a Super PAC (a PAC being a political action committee, an organization that pools donor funds to support or attack candidates, legislation, and policies) backing Romney’s candidacy showed actual baggage, labeled with Gingrich’s flubs over the years, tumbling down an airport carousel. The simple message it conveyed: nominating Newt would be political suicide for the GOP in a general election.

As September turned to October, November, and December, and as the days counted down to the Iowa caucuses, Romney’s struggles to overcome these minor candidates fascinated the media. Every new debate seemed to give someone else the chance to be the front-runner. And while the Democratic National Committee would dutifully attack whichever candidate happened to be leading the polls at the time, Obama’s senior advisors never wavered in their belief that Romney would be the eventual nominee.

Although the media outlets that hosted debates would order podium positions onstage based on polls of national primary voters—front-runners at the center, also-rans to the side—the real race for a presidential nomination is determined by the delegates needed at a convention. Cain, Bachmann, and Perry, even Gingrich from time to time, might lead a national poll, but Romney was besting everyone in surveys of Iowa and New Hampshire voters.

The Obama team, which prided itself on being steeped in the history of politics, knew the Republican trend: no candidate who had won either Iowa or New Hampshire, and then coupled it with victory in South Carolina, had failed to secure the GOP nod. Romney was leading in Iowa by a small margin, and he was miles ahead in New Hampshire. If he won both of the first two races, donations—the mother’s milk of presidential campaigns—to any other contender would evaporate (how things worked before one person could fund one Super PAC), and Romney could lock up the party’s nomination by mid-January.

The possibility that they would have an all-but-official opponent by mid-January gave the Obama team reason to worry. They knew they would likely be able to raise more money under existing campaign finance laws than any other presidential candidate in the country’s history; Obama, after all, had broken all the records in 2008, raising and spending almost $800 million. But campaign finance laws were changing, fast, and the new rules would give Romney an advantage Obama could never overcome.

It was a fear born of Obama’s firsthand experience in 2010, when he watched his party drown in a sea of outside money. A 2009 Supreme Court decision, Citizens United v. Federal Election Commission, had struck down a key provision of the Bipartisan Campaign Reform Act, better known as McCain-Feingold, and opened the door for unlimited political contributions by labor unions and corporations. Organized labor had already found ways around the prohibitions on political spending, so the decision was a much bigger benefit to Republican-backing corporations, which could suddenly funnel money to outside groups in larger amounts than ever before.

Another decision made in the Washington, D.C., circuit court, known as SpeechNow.org v. Federal Election Commission, allowed those independent groups to raise and spend unlimited sums of money on advertisements that directly endorsed a candidate.* The two decisions served as a reminder to individuals of their own unlimited donation rights, and they made the idea of giving money to a Super PAC rather than to, say, the Republican or Democratic National Committee much more appealing. Thanks to McCain-Feingold, a donor can give a certain regulated amount—currently about $32,500—to the national parties. Of that money, between 30 and 40 percent is spent on operations, staff, security, and maintenance of the two parties’ national headquarters buildings just a few blocks from the Capitol. But Super PAC donations are not capped, and the relatively low overheard required by a nearly anonymous (or in some cases entirely anonymous) outside group means that only the tiniest fraction of a big donor’s check, 2 or 3 percent in some cases, will go toward operations costs. The other 97 or 98 percent will go directly into advertising attacking a foe or supporting an ally. The courts’ decisions, in effect, made investing in outside groups rather than a national party a much more attractive prospect for a wealthy individual.

Obama hated what the Supreme Court had done, and not just because it neutralized his advantages. It struck at the core of what the former community organizer believed campaigns should represent: the collective will of thousands or hundreds of thousands. Organizing should be rewarded, not the wealth of one extremely affluent individual.

While a president usually offers little more than pro forma public disagreement with the Supreme Court—an equal branch of government, after all—Obama was so personally offended by the Court’s action that, less than a week after it issued its ruling, he used the biggest platform a sitting president has at his disposal, the State of the Union address, to publicly lambast the Citizens United decision: “With all due deference to separation of powers, last week the Supreme Court reversed a century of law that I believe will open the floodgates for special interests—including foreign corporations—to spend without limit in our elections. I don’t think American elections should be bankrolled by America’s most powerful interests, or worse, by foreign entities. They should be decided by the American people.”*

While Democrats had understood campaign finance regulations better in the early part of the decade, and accordingly built outside groups under sections of the Internal Revenue Code that allowed them to spend freely on campaigns and elections, Republicans were readier to take advantage of the new court decisions the second time around. Just after those 2009 decisions, Karl Rove and Mike Duncan, a former chairman of the Republican National Committee, had jumped at the opportunity to solicit money from wealthy donors and to spend it directly on candidates they backed. Democrats from across the country were inundated with negative advertising, and of course for Republicans, having an unpopular health care law and a high unemployment rate to run against helped.

In addition to American Crossroads and Crossroads Grassroots Policy Strategies, the twin organizations founded by Rove and Duncan and funded by the biggest donors within the Republican Party, other Super PACs quickly sprang up: Americans for Prosperity, the political arm of David and Charles Koch, two wealthy libertarian political activists from Kansas; the American Action Network, which eventually became the Super PAC wing of John Boehner’s political organization; the Congressional Leadership Fund, run by former top staffers to House Republican Eric Cantor, Boehner’s second in command and archrival until mid-2014, when he lost a primary for his House seat; and a host of other innocuous-sounding groups that could suddenly spend millions of dollars attacking Obama or any Democrat on the ballot.

Campaign finance debates are almost never successful ways to convert voters and win an election, and 2010 proved this again, but Obama’s focus on outside groups foreshadowed his fear that he would be their next victim. Every speech Obama gave in the run-up to the 2010 elections mentioned Rove or the Koch brothers or Super PACs and the corrupting influence of money in politics.

As Obama complained publicly about new sources of money in politics, hoping his holier-than-thou lectures would penetrate an electorate already saturated by Super PAC television advertising, anger among Democrats on Capitol Hill grew. They shared Obama’s outrage over the new money, but they faced the political reality that that new money was aimed at robbing them of their jobs; and they were the ones who had to win re-election now, in 2010. Obama was railing against the presence of outside money at exactly the time when House and Senate Democrats needed to build their own sources of outside money.

Obama’s opposition to outside groups had in effect frozen the Democratic donor community in 2010. Obama was signaling that the big donors who forked over their cash wouldn’t be rewarded with the traditional perks they had come to expect, and while Republican businessmen and megadonors were writing checks with abandon, Democrats were wondering why they should shell out big bucks for organizations that flew in the face of the way their president promised to do business. In 2010, Rove’s groups smashed through their fund-raising goals; their Democratic counterparts raised some money, but they almost struggled to keep the lights on. Democratic-leaning Super PAC television ads in 2010 were almost nonexistent.

Among the mantras that Rahm Emanuel preached as chief of staff was that political fund-raising should be kept as far away from the White House as possible. This reflected the political damage the Clintons had suffered when the public learned that major donors had been invited to stay overnight in the White House’s Lincoln Bedroom. Emanuel had even made clear that at least one top staffer in Obama’s 2008 campaign wouldn’t be welcome in his White House: Julianna Smoot, the campaign’s chief fund-raiser, was supposed to become head of White House personnel, but Emanuel vetoed her appointment, simply to eliminate even the illusion of fund-raising taking place on the White House grounds.

Emanuel’s position was in large part Obama’s position, too: unlike Bill Clinton, this president didn’t like socializing with donors, begging for another check by leveraging the trappings of the nation’s highest office. This was a case in which Obama’s personal loathing of political schmoozing fit his principles.

To many large donors and bundlers, those were clear signs that the unspoken tit-for-tat of political fund-raising was different in the Obama administration than it had been with the Clintons. Democrats who signed over big checks, or got their friends to do so, wouldn’t reap the traditional rewards of access and influence that they had come to expect. There would be no Lincoln Bedroom stays, no intimate cocktail parties with the president, no appointments to key or prestigious positions. And if writing a large check to a Democratic outside group wasn’t going to gain them access, or at least the thanks of a grateful president, why bother?

After the drubbing Democrats took in the midterm elections, the fear that Super PACs would play a significant role in 2012 took on new urgency. But then Team Obama caught a break. While Romney swatted away Bachmann and Cain and Perry, the Republican primaries had begun to resemble a playground for the rich and powerful. Santorum had surged at the right time, late in December. He and Romney had finished in a dead heat in Iowa; a recount of the delegates elected on Caucus Night showed the former Pennsylvania senator had actually eked out a victory over the once-unbeatable front-runner. Romney won New Hampshire, virtually his home state, but Gingrich charged to a surprising comeback and crushed the field in South Carolina.

The Obama team’s fear that their opponent would emerge unscathed in January after trouncing a field of nobodies evaporated. But their apprehension that a giant onslaught of money waited to bury them in a torrent of negative advertising built steadily, and for good reason: Santorum and Gingrich, it turned out, had some wealthy friends, and what both these candidates lacked in traditional campaign infrastructure, they made up for in überdonations.

For all his prominent staff and longtime associates, Gingrich had very few traditional resources with which to run a campaign. He had raised far less traditional money (in increments of $2,500 or less) than Romney, the barometer by which previously successful candidates can be measured. But when Gingrich finished a distant fourth in the Iowa caucuses, a lackluster performance that would have killed a campaign in any previous year, he wasn’t forced out of the race. Instead, his friend Sheldon Adelson, a billionaire whose fortune had been made and broken and made again as stock from his Las Vegas Sands Corporation bounced around in the volatile market, invested enough in a Super PAC to keep Gingrich alive. Adelson and his wife donated $10 million to a pro-Gingrich Super PAC run by a former Newt, Inc., staffer, and when part of that money flooded the South Carolina airwaves it handed Gingrich his bigger-than-expected victory.*

After Gingrich’s Super PAC bought the South Carolina primary win (helped by a stirring debate performance in which Gingrich attacked the moderator over a question about his personal life, thereby gaining the loyalty of conservatives who loathe the so-called mainstream media), it was on to Florida. Back in 2008, the Sunshine State had been the last stand for Rudy Giuliani, the candidate who was supposed to stop John McCain in his tracks. This time, Gingrich was all that stood in Romney’s way.

Anyone familiar with the rhythms of Las Vegas business was familiar with the Sheldon Adelson brand, but few had ever heard of Foster Friess, the wildly successful investment banker whose antipathy toward Romney would become yet another stumbling block to the nomination. Friess, who lived in the Wyoming woods, had helped Santorum build off his surprising Iowa upset, bankrolling another Super PAC that, although ostensibly independent from the Pennsylvania Republican’s presidential campaign, ended up carrying his message from coast to coast when the campaign itself ran out of money. Friess’s appearance in the late winter of 2011 created a strange cocktail of political players: an outside group backing Gingrich, bankrolled by a fantastically wealthy casino operator from Las Vegas, and an outside group backing Santorum, funded by an eccentric entrepreneur turned billionaire from the Wyoming wilderness. Those efforts kept two broke candidates in the game as another Super PAC, aided by less wealthy but equally determined Republicans for Romney, dumped their opposition research and their still considerable affluence not on Obama, but on Santorum and Gingrich. Plouffe and Messina could not have devised a better plan, and it was buying Obama precious time and wasting GOP resources.

The pro-Romney Super PAC demonstrated the ridiculousness of the new rules. Outside groups were ostensibly supposed to be run independently of a campaign, but the pro-Romney group was run by a prominent Republican operative, Carl Forti, who had been the Romney campaign’s political director in 2008. Forti shared office space with Alex Gage, one of the Republican Party’s top microtargeting operatives, whose wife happened to be employed as a top staffer on the Romney campaign. Forti was also the political director of Rove’s group, American Crossroads, which had declared neutrality in the primary process despite the fact that Rove, Duncan, and others involved in the Crossroads high command were all private fans of Romney and all but openly rooting for the former Massachusetts governor. Meanwhile Gingrich met frequently with the top donor to his supposedly independent Super PAC, and Santorum’s top benefactor was so closely linked to the campaign that Friess began appearing in the same sorts of sweater vests as Santorum.

To Obama’s senior advisors, the irony must have been immense: Romney could not become the nominee until he bested the Super PACs run by other Republican candidates. But once a nominee emerged, the onslaught of Super PAC advertising, from the pro-Romney group to Foster Friess to Sheldon Adelson (who voiced, and delivered on, a promise that he would spend $100 million to beat Obama), would turn exclusively toward the president. Speaking at the 2013 White House Correspondents’ Dinner, Obama told Adelson, who was not present, that the billionaire would have been better off simply offering him $100 million not to run. He would have turned him down, Obama joked, but he might have thought about it.

As the Obama team watched the ugly, heated Republican primary, they began agitating for a solution to a problem they could see coming: they needed a Super PAC of their own. Once again it fell to Jim Messina to fight the battle inside the White House. He took it upon himself to begin the lobbying on behalf of what would prove to be a major flip-flop by a politician who prided himself on not changing his mind. In order to survive in this new landscape, the president now needed to signal to major Democratic donors that donating to Super PACs would be acceptable.

With other issues on which Obama had flip-flopped—the health care mandate and expanded use of drones, among others—the president had been persuaded by data, or at least he needed the data to justify the flip-flop. So Messina used data to make his case. On a whiteboard in his office, the campaign manager began doing the math. Showing what Republican Super PACs had raised during the 2010 elections, incorporating what Romney’s Super PAC had already raised from the former Massachusetts governor’s rich private sector friends, and including a few extrapolations based on public declarations by the outside groups that backed Gingrich and Santorum, and the ones funded by the Koch brothers, he estimated that the Obama campaign would face about $660 million in outside spending alone over the coming months. And that didn’t include the $600 million to $1 billion Messina estimated that Romney would raise for his own campaign once he was the official nominee.

Messina asked Axelrod to a meeting in his new office in Chicago. Axelrod, who had been involved in every Obama campaign since the 2004 Senate race, had never seen Obama outspent. As both men knew, one of the secrets of Obama’s success had been his ability to do what many Democrats rarely do: raise and spend more than his opponents. When he launched his campaign in 2007, Obama had pledged to abide by rules that restricted how and where a presidential candidate could spend his or her money; he quickly broke those rules when his campaign raised more than it had ever anticipated. In doing so, Obama became the first candidate in the post-Watergate era to abandon voluntary fund-raising guidelines, because his campaign could then attract more than it could sticking to the rules for general election matching funds. But given the Republican outside groups, Rove’s organization, and Romney’s fund-raising prowess, Obama’s financial acumen wasn’t going to be a given advantage this time around.

Who could establish the Democratic alternative to Karl Rove? Rove was a known quantity, one of the Republican Party’s best fund-raisers, given his strong ties to the big-donor community. Crossroads had proved itself calculating and influential in 2010, when it helped Republicans take back the House and win back seats in the Senate. Since Obama’s 2012 campaign was going to retain the brain trust—Plouffe, Axelrod, and Messina—who would serve as the surrogate, the Obama insider able to convince donors who had already given the campaign the maximum allowed by law to pledge even more money to an outside group?

Besides Robert Gibbs, perhaps no one else had spoken more on Barack Obama’s behalf, either as a candidate or as president of the United States, than Bill Burton. Though he was much younger than others who might have run an outside group and didn’t seem to be someone you could picture wooing some of the wealthiest people in the country, people who might be inclined to fork over a seven-figure check, Burton had an impressive enough résumé. He had run communications for the Democratic Congressional Campaign Committee when Rahm Emanuel had been its chairman, and he had worked in the press shops for Dick Gephardt, John Kerry, and Tom Harkin at various points during his time in Washington. He’d even done some time in Iowa in 2004 for Gephardt’s unsuccessful presidential campaign.

Burton had signed on to Obama’s campaign almost from the beginning. He had been through the pressure cooker of the 2008 primaries and survived most of the first term even as Gibbs had become an increasingly controversial presence in the West Wing. When Gibbs made official his decision to leave in late 2010, Burton was an obvious candidate to take over the press room podium, perhaps the most prominent job in his profession.

But Burton wasn’t the only candidate, and eventually he fell victim to the “deputy” syndrome that happens in any organization when the boss simply can’t envision the number two as the chief. Going outside the West Wing altogether, Obama tapped Jay Carney, the former Time magazine correspondent and spokesman for Vice President Joe Biden. The same day Carney took over the podium from Gibbs, on February 16, 2011, Burton announced that he would leave the White House, the barest hint of internal strife peeking out.

When it became clear to Burton that he wouldn’t be getting the podium, his friend Sean Sweeney, a top Emanuel aide, suggested that the two form a consulting firm.9 After all, two top advisors to a sitting president could leverage their relationships in Washington in lucrative ways. Plus, neither wanted to go to Chicago to work on the campaign; Burton’s wife, Laura, was pregnant with the couple’s first child, and moving halfway across the country to work twenty-hour days didn’t much appeal to Burton.

At the same time, Karl Rove and the Koch brothers were making their plans known. Rove’s Crossroads organization announced that it would spend $120 million on Republican causes. Americans for Prosperity, the Koch brothers’ outside vehicle, said its goal would be to raise $88 million to defeat the president. Sweeney broached an idea with Burton: with all the outside money aimed in Obama’s direction, why don’t we found a group that can fight back?

In 2010, the White House had shouted down efforts to found, and properly fund, a real Super PAC to help congressional Democrats. In doing so, it had ensured that its own party would be bringing a knife to a gunfight. Now, Burton and Sweeney—former aides who would avoid tainting the White House with the stain of outside cash but were close enough that they could give donors the impression they were speaking for the White House—would help their old colleagues fire back with equal force.

Burton and Sweeney signed up some of the best Democratic strategists in the business, many of whom had long histories in Bill Clinton’s White House. Harold Ickes, in 2008 a fierce Hillary Clinton defender, became the group’s president; Paul Begala, the strategist who had helped guide Clinton’s 1992 campaign and remained close to the Clinton family, would serve on its board of directors. Hiring the former was somewhat tricky. There had been rumors for months that Ickes, still fuming at having a donation he made to Obama and the DNC rejected because he was a registered lobbyist, had been shopping around for someone to challenge Obama in a primary. This never got anywhere, a pipe dream of the formerly well-connected Democrat who believed—like many a Washington Democrat over the age of fifty—that he’d never gotten the respect he deserved from the Obama White House. But Ickes had big-time labor connections, something this new Super PAC needed; and whether Ickes liked it or not, Obama was the party’s guy, and Ickes was a party guy at the end of the day.

Priorities USA filed its papers with the Federal Election Commission a few days later, on April 29, 2011. The first check came from Jeffrey Katzenberg, CEO of the movie studio DreamWorks, in the amount of $2 million. The Service Employees International Union, which had spent the past two decades building its prominence as a first-among-equals partner of the labor coalition, pledged $1.5 million. Those donations turned the lights on, in Burton’s words, and allowed the group to begin hiring staff and renting office space.

But they would be frugal, and they saved money in every way possible. They could find office space only through October 31, so instead of spending another several thousand dollars on rent for November, the Super PAC would end up homeless on Election Day, using laptops from home or coffee-shop WiFi to tie up any loose ends. Of course, a Super PAC’s real work is all done a week out from the election.

Katzenberg and SEIU had been quick with their checkbooks, but their generosity didn’t translate to more contributions. Donors told Burton and Sweeney they were leery of getting involved in a Super PAC after the president had spent so much time recounting the evils of outside money. After the initial elation at raising $3.5 million from exactly two donors, the money slowed to a trickle, and it became clear the operatives would have to spend much more time convincing and cajoling than they would scripting and filming advertisements. It didn’t help that the New York Times ran a front-page story featuring photographs of Burton and Katzenberg; the next day the paper, famously opposed to money in politics in any form, wrote a scathing op-ed taking both men to task. “A lot of donors that we went to, that was their top concern,” Burton said. Conservative donors laugh at a New York Times editorial about big money; liberal donors feel shame. Translation: the Republican Super PACs were having no such trouble raising their own money. In fact, in September 2011, the Crossroads organizations said they would double their fund-raising goal, to $240 million.*

In 2011, the monthly Super PAC reports comparing Republican donations to Democratic ones were embarrassing for Burton’s group. The low point for Burton and Priorities was their February 2012 Federal Election Commission report: that month they’d raised less than $60,000 total while Mitt Romney’s Super PAC had pulled in more than a hundred times what Burton had—over $6.6 million, to be exact. In fact, the average donation to Romney’s Super PAC in January (which the February report reflected) was just under $48,000, within striking distance of what the president’s unofficial Super PAC raised for the entire month, period. And this was just one pro-Romney Super PAC—what Rove’s Crossroads and the Koch brothers’ Americans for Prosperity were raising and spending was equally intimidating to the Democrats.

Burton needed help, and he needed the president to bless the Super PAC; until and unless the president did that publicly, they were going to struggle to raise money.

But within twenty-four hours of finding out just how poorly his fund-raising was going, the president gave Burton a thumbs-up. Obama himself didn’t announce the reversal. It was done via conference call by campaign officials, who asked that the exchange be kept on background—a signal that the president wasn’t exactly proud of this decision. It was clearly not something they were excited about doing, but something they felt they had to do. It was going to fall to Plouffe and a few other prominent Obama surrogates to actually show up and raise money for this Super PAC the president never wanted. Obama himself stayed away from Super PAC fund-raising in 2012, but by 2014, he started helping personally. And he rarely spoke out about campaign finance issues after 2012.

While hanging on, Santorum and Gingrich toyed with the idea of running as a ticket in their stop-Romney efforts, but those talks died when neither candidate could agree on who was top dog. So knowing how important it was to knock Santorum out for good, as the April 3 Wisconsin primary approached, Romney courted one last Republican establishment figure with his finger on the pulse of the new conservative movement: Wisconsin’s own Paul Ryan, who had stayed silent on the presidential race for months.

Ryan had long been a Romney admirer, though he saw no political advantage in endorsing a candidate early. And since Ryan himself had toyed with a 2012 bid (even discussing running as late as August 2011 while vacationing with his family in Colorado), he figured he might as well wait until his endorsement mattered. He went for Romney just before the Cheesehead primary, and to his surprise, once he hit the trail, he discovered a rapport with the former Massachusetts governor. They geeked out together on budget wonkery and developed a real intellectual bond. And while few people could make the normally stiff and reserved Romney crack a smile, Ryan got the candidate laughing. Romney advisors took notice.

Following his victory in Wisconsin, Romney ran off wins in every subsequent primary, and as the end of April approached, the Republican National Committee formally declared Romney the presumptive nominee (in fact the RNC had been working closely with Romney’s campaign for almost a month beforehand, though privately, in order to avoid a backlash from conservatives committed to Gingrich or Santorum).10 With that, the general election began.*

Obama faced two opponents as the general election loomed: Romney, who though his campaign appeared hapless at times was still the formidable opponent Obama’s team had worried about since 2008, and the economy, which appeared to be slowing precisely at the most inopportune time for the president. The nation’s unemployment rate stood at 8.2 percent, well off its highest figure but still in dreadful territory. Perhaps more frightening, the pace of job creation had slowed markedly; after a robust 275,000 new jobs in January 2012, the Bureau of Labor Statistics reported the economy had added just 120,000 new jobs in March. The unemployment rate fell to 8.1 percent in April, but the economy added an even more anemic 115,000 jobs. The grim truth was that the unemployment rate had fallen only because more Americans had stopped looking for work, and thus weren’t counted as part of the workforce. And then there was an unpredictable decision on the legality of the president’s health care plan that the Supreme Court was due to hand down in June—a lot of unknowns out of the campaign’s control, and a scary proposition for Plouffe and Messina.

Most polling in April showed Obama’s approval rating hovering in the mid–40 percent range. Less than a third of voters believed the country was headed in the right direction, and almost two-thirds thought America was on the wrong track. Public surveys showed him barely ahead of, if not tied with, Romney, who hadn’t yet had a chance to make his case directly to the electorate; Republican-leaning pollsters even showed Romney ahead.

The advertisements blasting Romney as an out-of-touch businessman bent on protecting the rich were written and waiting to be produced and aired in key swing states. But there was no way to advertise against the economy or to tout Obama’s record as good enough in an atmosphere in which Americans clearly didn’t believe things were headed in the right direction. By 2012, Americans did not believe they were better off than they had been when Obama assumed office, and the track record on this issue was pretty clear: If Americans believed they were better off, they usually rewarded the incumbent or his party. If they didn’t think so, electoral upheaval was imminent.

On the other hand, the Obama team could try to change the discussion to something more forward-looking that would help them avoid the uncomfortable truth that Americans didn’t feel terribly happy with the results, or lack thereof, of the president’s performance. Plus they did have one thing going for them when it came to the economy: voters did not blame Obama for the economy, they blamed Bush, even as late as 2012. And so the Obama campaign took on the unprecedented task of persuading voters to ask themselves a different question: will you be better off in four years under Barack Obama than you would be under Mitt Romney?

This wasn’t an original strategy. John Kerry’s advisors had believed in their hearts that 2004 would be a referendum on Bush. The Bush team feared that, and instead sought to change it from a “referendum” to a “choice” concept. It had worked for Bush, and now Team Obama was adopting the same strategy.

Throughout the summer of 2011, when most of Washington was obsessed with negotiations over raising the debt ceiling, a small team inside the White House set to work on the American Jobs Act, a largely symbolic piece of legislation that would serve primarily as a messaging vehicle for the beginning of the campaign. Plouffe, Stephanie Cutter, Bill Daley, Tim Geithner, and Gene Sperling spent hours designing the bill, which they would pitch as a solution to the stagnant recovery.

In part, this was an exercise in team building. The White House couldn’t simply ask for more tax cuts, because it needed Democrats not only to support the bill but to show a unified front. The point was to design a bill that would mobilize a variety of constituencies that wouldn’t get off the bench without an incentive to do so. What it was not designed to do was to be passed by Congress. This was about giving the president something to run on—and, when summarily rejected by the GOP, something to run against.

Obama introduced the plan in an address to a joint session of Congress on September 8, 2011. The American Jobs Act would cut taxes on businesses that hired workers or raised salaries; spend money repairing infrastructure and upgrading roads, bridges, and even the nation’s air traffic control system; and modernize 35,000 schools, another infusion of infrastructure funds that would put people to work quickly. It would appropriate money to hire new teachers and to provide summer jobs for young people; it even specifically incentivized hiring workers who had been out of work for more than six months. At every turn Obama emphasized the bipartisan elements of the bill, and yet it was hardly a plan the White House thought had much of a chance to be enacted—which was just fine with Plouffe.

The speech was aimed directly at the middle of America, the swath of voters who would make the choice the Obama team was trying to set up. The media, Obama told the gathered members of Congress, had been asking, “ ‘What will this speech mean for the President? What will it mean for Congress? How will it affect their polls, and the next election?’

“But,” he explained, “the millions of Americans who are watching right now, they don’t care about politics. They have real-life concerns.” It was a nice thought, though the speech, and the bill itself, had been written with exactly those very political questions in mind.

Three months later, Obama gave a second speech aimed at framing the same choice. This one came in Osawatomie, Kansas, a town of just 4,447 people that lies an hour south of Kansas City. Obama’s trip to a deep-red part of a deep-red state—he ended up losing Miami County, where Osawatomie is located, by a 66 to 32 percent margin in November11—wasn’t aimed at winning those specific electoral votes in Kansas. Instead, he hoped to draw a clear comparison to one of his predecessors, one who had drawn a similar contrast in his own election campaign: Theodore Roosevelt.

Nothing irks Obama more than the idea that he’s somehow a leftist or liberal; he believes that most of his ideas are old Republican ideas from another era. That last phrase is the key—these are almost always ideas that would fail on the runway with today’s GOP. And it isn’t clear that his support of them has done much to change existing Republican minds, either, just as Republican claims that JFK was a tax cutter rarely persuaded Democrats to jump the fence.

But policy specifics aside, Obama’s big speeches on the campaign trail weren’t so much about doing something new as about finding a historical hook to justify his position, so it was to the history books that his speechwriters turned.

On August 31, 1910, Roosevelt stopped in Osawatomie to call for what he dubbed the “New Nationalism.” He argued that only the federal government had a reach broad enough to provide for human welfare; he called for a national income tax, national laws to protect the rights of children and women in the workplace, and more oversight of the nation’s banking system. “I do not ask for the over centralization; but I do ask that we work in a spirit of broad and far-reaching nationalism where we work for what concerns our people as a whole. We are all Americans. Our common interests are as broad as the continent,” Roosevelt said.12

Obama’s team didn’t want to draw too direct a comparison to the New Nationalism—Roosevelt had given the address almost two years after leaving the White House, just before he ran for a third term on the Bull Moose ticket, and he lost the 1912 election badly. Instead, Obama used the address to call his proposal for an extension of a middle-class tax cut a “square deal,” the phrase Roosevelt had used to describe his program of domestic initiatives. And much of his speech would have sounded familiar to Teddy himself.

“For most Americans, the basic bargain that made this country great has eroded. Long before the recession hit, hard work stopped paying off for too many people,” Obama said. “This is not just another political debate. This is the defining issue of our time. This is a make-or-break moment for the middle class, and for all those who are fighting to get into the middle class. Because what’s at stake is whether this will be a country where working people can earn enough to raise a family, build a modest savings, own a home, secure their retirement.”13

Obama’s position thus defined, he set up the choice his campaign wanted Americans to face: “In the midst of this debate, there are some who seem to be suffering from a kind of collective amnesia. After all that’s happened, after the worst economic crisis, the worst financial crisis since the Great Depression, they want to return to the same practices that got us into this mess. In fact, they want to go back to the same policies that stacked the deck against middle-class Americans for way too many years. And their philosophy is simple: We are better off when everybody is left to fend for themselves and play by their own rules,” Obama said.

He went on: “I am here to say they are wrong. I’m here in Kansas to reaffirm my deep conviction that we’re greater together than we are on our own. I believe that this country succeeds when everyone gets a fair shot, when everyone does their fair share, when everyone plays by the same rules. These aren’t Democratic values or Republican values. These aren’t 1 percent values or 99 percent values. They’re American values. And we have to reclaim them.”14

“Osawatomie really framed the campaign,” Valerie Jarrett would say later. “The thought that went into that speech was, ‘What’s going to be our theory of the case for re-election? What’s going to distinguish the president from whoever ultimately wins the [Republican] primary?’ ” For Plouffe, the speech was the beginning of a simpler mission: “We’re just going to repeat the same thing, over and over again: Fair shot, fair shake.”*

Obama’s team had already planned its main lines of attack: Romney’s business record and his penchant for flip-flopping as he’d disavowed position after position when moving to the right. Gingrich, Santorum, Perry, and the other anti-Romney candidates running in the primaries had seen some success doing the same thing but focusing on his past preferences as opposed to his current beliefs, but Obama’s labeling Romney a flip-flopper might cause him trouble with a Republican base already skeptical of the president’s record.

Thus the campaign slowly moved away from the flip-flopper label. Messina, Axelrod, and Plouffe began to have doubts that the strategy would work in a general election—doubts echoed by Bill Clinton, still one of the best political strategists in the country, who ultimately was the one who convinced them to give it up entirely. Clinton told Messina to step away from the flip-flopper line of attack. Clinton, himself accused of being a flip-flopper, knew that this could actually be a strength, a coded message to suburban voters that Romney would take the centrist position and was secretly a moderate.

The most promising angle for contrasting Romney and Obama was the very strength that made Romney a viable candidate in Massachusetts and the front-runner for the Republican nomination: his background as a successful businessman and turnaround artist.

Romney was the classic example of an overachiever. Married to his high school sweetheart, possessed of a top-notch mind for business, generous with his ample wealth, and, thanks to his strict observance of his Mormon faith, unblemished by personal skeletons anywhere near his closet, Romney seemed to offer nothing to an opposition researcher looking for juicy tidbits. His greatest scandal, it seemed, was that he had once lost his temper with a police officer in the early 1980s and was briefly detained. Compared with recent presidents—an impeached philanderer, a recovering alcoholic, and Obama, who went so far as to detail some of his hard drug use in his memoir—Romney was untouchable on the personal front.

Romney’s wealth came from the world of private equity, a cutthroat line of work in which businesses leverage their access to huge amounts of wealth to buy other businesses and make them profitable. Romney often touted his work with companies such as Sports Authority and Staples to show he had spent his time in the private sector turning failing companies around and saving jobs in the process. At a moment when the U.S. economy needed its own turnaround artist, that sounded like a winning biography. Simply being described as a “businessman” invariably had what political strategists call a “halo effect” with voters, for any candidate during any period. So imagine how well a candidate who was described as a “successful” businessman would be received in the midst of a recession.

Yet for every Sports Authority or Staples, there were companies like Holson Burnes Group, Cambridge Industries, and GS Industries. All three of those smaller firms shared common themes: they had once employed hundreds of workers in skilled manufacturing jobs. Holson Burnes made photo albums and picture frames in Gaffney, South Carolina.15 Cambridge made plastic parts for automobiles in Michigan. GS Industries was a Kansas City–based steel manufacturer. In each case, Bain Capital, under Romney’s management, had purchased the firm and then charged it eye-popping management fees while loading the company with debt. For example, Bain would borrow against the assets of a troubled company and use the cash for new investments, including the purchase of other companies. This was a way to leverage an investor’s money; instead of relying on one turnaround, the assets of one troubled company could be used to buy a new one without asking for more new cash from the investor, thus giving an investor two separate shots at making money with the same dollar. In each case, the debt proved too much for the small company to handle: factories were closed, workers were laid off, jobs either disappeared or moved overseas—and Bain still raked in millions, because bankruptcy didn’t cost Bain’s investors anything. Bain had more successes than failures, and with the failures it did have, it was able to keep its eventual losses to a minimum, since it stripped those companies of all their assets before bankrupting them. This is a crude shorthand description, but it represented capitalism in its purest survival-of-the-fittest mode.

During the fifteen years Romney ran the company, Bain bought controlling stakes in more than forty businesses. At least seven, including Holson Burns, Cambridge, and GS Industries, filed for bankruptcy while Bain held a controlling stake, according to a review by two New York Times reporters.

For a private equity firm, more than thirty successes compared with just seven failures is an outstanding record, one with which most blue-chip firms can’t hope to compete. But the seven failures meant hundreds, if not thousands, of jobs lost; couple those with the big profits Bain made while the companies were failing—$10 million from Cambridge alone16—and the negative advertisements virtually wrote themselves. All the Obama campaign had to do was find a former employee of one of these companies and invite him or her to talk about the experience of getting laid off by a company Romney controlled.

Romney had a habit of exacerbating his greatest weakness. He would occasionally make offhand references to his personal wealth or to his wealthy friends. In February 2012, when he was asked during a visit to Daytona, one of NASCAR’s holy sites, whether he followed auto racing, Romney replied that he didn’t follow the sport closely. But, he said, “I have some friends who are NASCAR team owners.”17 Two weeks later, while appearing on a radio program in Alabama, Romney was asked where he thought Indianapolis Colts quarterback Peyton Manning, who was looking around for a new team, should go. Romney said he didn’t want Manning playing anywhere near New England, then added, apropos of nothing at all: “I have a lot of good friends, the owners of the Miami Dolphins and the New York Jets—both owners are friends of mine. But let’s keep away from New England so that Tom Brady has a better of shot of picking up a championship for us.”18 The one sport he was very familiar with was something only the wealthy could afford: an equestrian sport called dressage.

The sports references were easy to make fun of and made stereotyping him as a rich guy easy, but one comment stuck in the Obama team’s mind: in August 2011, when a protester at the Iowa State Fair yelled at Romney to raise taxes on corporations, Romney had put the man in his place. “Corporations are people, my friend,” Romney had retorted. “Everything corporations earn ultimately goes to people. Where do you think it goes?”19 That gem got its own special place in Obama campaign talking points.

Obama’s travel schedule during his first three years in office already resembled a campaign flight plan. He stopped much more frequently in swing states than he did in run-of-the-mill noncompetitive states. So traveling back to Columbus, Ohio, and Richmond, Virginia, to campaign was no different from the schedule for any other week. This time, however, Obama would be framing the argument against Romney himself—the first time the president had directly engaged his opponent and made the case not against a generic “them,” but against a specific person. And in a thirty-five-minute stump speech at Ohio State University on May 5, 2012, he was as subtle as a hammer in framing the question that would soon be before voters.

“After a long and spirited primary, Republicans in Congress have found a nominee for president who has promised to rubber-stamp this agenda if he gets the chance,” Obama said. “We cannot give him that chance.”

Then came the reframe: “The other side… won’t offer a better vision or a new set of ideas. But they will be spending more money than we’ve ever seen before on negative ads, on TV, on radio, in the mail, on the Internet—ads that exploit people’s frustrations for my opponent’s political gain. Over and over again, they will tell you that America is down and out, and they’ll tell you who to blame, and ask if you’re better off than you were before the worst crisis in our lifetime. We’ve seen that play before. But you know what? The real question—the question that will actually make a difference in your life and in the lives of your children—is not just about how we’re doing today. It’s about how we’ll be doing tomorrow.”20

As Obama looked around the arena that day, he couldn’t help but notice a difference from four years before: When the Buckeyes played a basketball game, the Schottenstein Center at Ohio State University held a full capacity of 18,300 spectators. But as he kicked off his re-election bid, Obama—who in 2008 had been besieged by crowds numbering in the six figures, both at home and overseas—stared out at 4,000 empty seats. He would have to remember to speak to someone on his campaign staff about that. If, after all, there was a real enthusiasm gap, if the hundreds of thousands, if not millions, of new voters the 2008 campaign had identified, registered, and turned out simply weren’t interested or inspired this time around, the campaign was going to have a real problem.

The crowd in Richmond, on the campus of Virginia Commonwealth University, was smaller, but packed in tighter. Yet for some reason no one was standing behind the president, which left him oddly alone in the camera shot. Obama’s campaign, it seemed, was starting off with a few minor missteps—not so terrible that a voter would notice, but troubling nonetheless, and the kinds of mistakes Obama’s campaign hadn’t made four years ago. If the campaign was missing small details, when would it miss a larger one?

Obama didn’t know that in fact, a larger misstep had already occurred. In an interview marking the campaign kickoff on NBC’s Meet the Press, taped the same day Obama was speaking in Columbus and Richmond, Biden had hit all the right notes, defending the administration’s record on the economic recovery while taking Romney and his business career to task. Host David Gregory then asked the vice president about same-sex marriage. Biden managed to dodge the question twice, but when Gregory asked a third time—“And you’re comfortable with same-sex marriage now?”—Biden strayed from his talking points.

“I am vice president of the United States of America. The president sets the policy.” (And hard stop—or so the campaign wished Biden would have done, but he didn’t. He kept talking.)

“I am absolutely comfortable with the fact that men marrying men, women marrying women, and heterosexual men and women marrying each other are entitled to the same exact rights, all the civil rights, all the civil liberties. And quite frankly, I don’t see much of a distinction beyond that,” Biden said.

The Obama campaign had known it was going to have to deal with same-sex marriage at some point. The liberal base of the Democratic Party was simply too supportive of gay marriage to allow their platform, or their president, to stay silent. It was something the campaign was worried could become a distraction at their convention in September if they didn’t do something. Still, this wasn’t how they wanted to deal with it. Because now, if Obama didn’t back same-sex marriage by the time the Democratic convention rolled around in September, he would face an embarrassing fight on the convention floor, something the optics-obsessed campaign wanted to avoid at all costs.

When the president himself decided to change his mind is less than clear. By 2008, it wouldn’t have been a surprise for a Chicago liberal to be in favor of gay marriage. But Obama, then and earlier, had always followed the moderate Democratic candidate’s playbook when it came to social issues, including abortion and gay rights, even guns; in fact, he sounded like a Southern Democrat when it came to those issues for much of his short career in the Senate. Gay rights activists then turned up the heat, big-time, starting in 2010 and continuing in 2011, interrupting Obama’s large, low-dollar fund-raisers as well as more intimate high-dollar settings, demanding to know why the president was suddenly behind where every other Democrat was on the issue of marriage.

Senior White House staffers—Pfeiffer, Plouffe, Axelrod, and Cutter—had been working since the summer of 2011 on a strategy to allow Obama to come out in favor of gay marriage. They kept their deliberations muted and their group small, to prevent leaks, for fear it would look ham-handedly political, which, well, it was. And they had settled on a venue: The View, a daytime program that drew a sympathetic audience, had largely sympathetic hosts, and would give Obama time to explain his personal evolution on gay marriage without an interruption. The appearance was less than two weeks away when Biden stole Obama’s thunder and turned the president into a follower of his own vice president.

So how did Biden so easily get pushed off message? The backstory was that a few weeks before his Meet the Press appearance Biden had been at a fund-raiser in Hollywood, where a gay couple had opened their mansion to the campaign. There, Biden had met the couple’s young son. What are we doing, Biden wondered, opposing gay marriage, when this kid has a loving home? Biden later called the moment his epiphany, a strong word for a lifelong practicing Catholic that underscored the impact he had felt.

It was classic Biden, who wore his heart and more on his sleeve. It was Biden being Biden. But he’d gotten out in front of a major policy change, and that required damage control.

Biden hadn’t known the senior advisors were plotting Obama’s public about-face for The View, and when he found out about it, he felt even worse. His advisors, always conscious of the vice president’s place within the White House hierarchy, scrambled to let the president’s team know just how bad he felt.

To know Biden was to know how he easily could have stumbled into this, but at least initially, some in Obama’s orbit believed the vice president had pulled a fast one, zipping out in front of the president to score points with a base he would need if he wanted his own shot at the Oval Office in 2016. (Messina especially has always been skeptical of Biden’s motives.) Obama never believed that Biden had jammed him intentionally. Still, it was a big stumble, more for the timing than anything else, knocking the president off message in the most important week of his re-election push: the campaign kickoff week!

Biden’s flub, the empty seats in Columbus, the visuals of the stage in Richmond—these mistakes were minor, but they hinted at deeper problems. Obama came away from his first week back on the trail chastising staff, urging them to button up and get their acts together. Even Michelle Obama expressed her dissatisfaction with the little ways the campaign wasn’t executing perfectly. It was particularly unnerving for Team Obama that the announcement week went as poorly as it did, since they’d had months to prepare for it. Their plan had always been to announce in either late March or early April, and they would have done it even sooner had Romney wrapped up the nomination earlier. But the longer the GOP primaries went on, the more time the campaign bought for planning the announcement. They never thought they’d get to wait until May to announce, and yet the extra time hadn’t ended up in a smooth launch.

But the arc of the campaign’s message had less to do with those early rallies than with the advertising it was about to launch. Anticipating the piles of secret Super PAC money that was sure to rain down on their heads at any moment, the Obama campaign had always planned to get on television first. They would be outspent, but with a little strategic thinking they could determine the story the media would write on any given day by being first—first to run television ads, first to put the candidate on camera, and first to viciously attack the straw man they would create, the one with the Mitt Romney name tag.

As Cutter prepared to pull the trigger on the Bain attack ads, she warned her fellow senior strategists that their line of attack wasn’t wholly without risk. Here was a Democratic candidate who already had a difficult time getting along with business, about to use business as an excuse to vote against the other guy; class warfare doesn’t always help the side attacking the rich. Plenty of Democrats, Cutter predicted, especially those from the Acela Corridor (folks who live between New York City and Washington), would question their strategy: was Obama attacking business itself?

Axelrod, for one, was nervous that some of the ads would come across as too negative. But Cutter argued that the campaign couldn’t flinch. “We can’t do this half-assed,” she told Plouffe, Axelrod, and Messina. “Either we’re going to do it with gusto, or we’re not going to do it.” And Plouffe had an iron stomach—he wanted to hit Romney, and hard.

The first advertisements Obama’s team had run, beginning way back in January, had largely been positive spots. Then, on May 14, Cutter and Larry Grisolano introduced Joe Soptic, a steelworker from Kansas City who had lost his job when Bain Capital came to town. In a two-minute spot, Soptic, near tears at times, and several of his former coworkers castigate Bain and the men who ran it for sucking the money out of GST Steel, a part of GS Industries. “It’s like a vampire. They came in and sucked the life out of us,” says Jack Cobb, another former steelworker. “We view Mitt Romney as a job destroyer,” says John Wiseman, a third man who lost his job.

The amount of money Obama’s campaign spent on the two-minute ad was relatively small—it was a “show buy” in political parlance, aimed as much at earning media attention, and thus new eyeballs the campaign didn’t have to pay for, than at actually persuading voters.

Cutter had been right to predict trouble ahead. The Sunday after launching the attacks on Bain, Cory Booker, the young mayor of Newark, New Jersey (hence resident in the Acela Corridor), who was fast becoming one of the media’s favorite Obama surrogates, voiced his discomfort with the president’s line of attack. “I have to just say, from a very personal level, I’m not about to sit here and indict private equity,” Booker said on Meet the Press. “If you look at the totality of Bain Capital’s record, they’ve done a lot to support businesses, to grow businesses. And this to me, I’m very uncomfortable with.

“This kind of stuff is nauseating to me on both sides,” Booker went on. “It’s nauseating to the American public. Enough is enough. Stop attacking private equity. Stop attacking Jeremiah Wright.”21

The Wright reference was particularly jarring. The week before, news had leaked that conservative billionaire Joe Ricketts—founder of TDAmeritrade and owner of the Chicago Cubs—was planning a major advertising campaign that would once again bring up Obama’s former minister, forcing the Obama campaign to stay adept at making sure any Wright reference was viewed solely as a racial attack whether it was intended or not. It took Ricketts all of about twenty-four hours to pledge not to run the Wright spot after mainstream Republicans denounced the tactic.

As for the Bain attacks, Booker wasn’t the lone Democrat wetting himself, as Plouffe often described squeamish Democrats. Former representative Harold Ford, another young African American leader who had decamped to New York after losing a Tennessee Senate race in 2006, and former Pennsylvania governor Ed Rendell, one of the stalwarts of the Northeast Democratic establishment, joined Booker in his complaint. The Bain ads were “very disappointing,” Rendell said.22 So the Obama campaign moved swiftly to snuff out dissent. The very afternoon Booker was on Meet the Press, he was deluged with attacks from the left on social media; it got so bad that he decided to film a video from his office in Newark reiterating his support for the president. Tieless, direct-to-camera, Booker completely walked back his criticism of the Bain Capital ad: “Mitt Romney has made his business record a centerpiece of his campaign. He’s talked about himself as a job creator. And therefore, it is reasonable, and in fact I encourage it, for the Obama campaign to examine that record and to discuss it. I have no problem with that,” Booker explained. Republicans mocked it as a hostage video. They weren’t that far off: someone from Chicago had very clearly taken Booker to the woodshed. Interestingly, this was a rare instance in which the president okayed a hardball tactic like that, something that would have made LBJ or Bill Clinton proud. Oddly, the president has never had trouble playing hardball with members of his own party; it is figuring out how to play hardball against the GOP that has always eluded him.

Still, the Bain attack launch provided more evidence to the president that key surrogates were not prepped on their strategy, and that the campaign, as it kicked off, looked sloppy. A few weeks later, after one more self-inflicted wound, Obama would reach his wits’ end and let his team have it.

Cutter had built a network of more than 1,000 surrogates in every state and city of significant size, and she sent one of her most prominent stand-ins, David Axelrod, to Boston. Axelrod would appear on the steps of the Massachusetts state capitol, on Beacon Hill, to try to undermine the other foundational pillar of Romney’s record—his term as governor.

Voters have an inherently positive view of governors; their executive experience lends them credibility, and their distance from Washington gives them the opportunity to run against a political culture most voters believe needs change and an outsider’s perspective. (It’s no coincidence that four of the last six presidents—Carter, Reagan, Clinton, and George W. Bush—had governed a state as their last elected job before being elevated.)

Romney’s record, Axelrod said, was “alarmingly weak.” During his tenure, Massachusetts had been forty-seventh among the states in job creation—a statistic the campaign would repeat endlessly during the following months—and that state’s government had grown six times faster than the private sector had.

But holding an event in Boston came with a built-in risk: Beacon Hill was just a few miles from Romney’s headquarters, where hundreds of staffers and volunteers worked feverishly for their man. The Romney campaign held a conference call the night before Axelrod’s event, then mobilized what seemed like every supporter they had in the greater Boston area. By the time Axelrod showed up, he found as many Romney supporters as Obama supporters waiting for him.

In hindsight, this event was emblematic of what would become one of the more uninspiring political campaigns of the modern era. The two sides competed for attention. Obama fans screamed their man’s signature chant—“Fired up, ready to go!”—while Romney supporters yelled back, “Solyndra!” “Forward!” the Obama team shouted. “Off a cliff!” the Romney partisans shot back. One Romney staffer, a member of the advance team, blew bubbles at Axelrod while the campaign’s senior strategist spoke.23

Back in Washington, Obama was beside himself. He watched coverage of the Axelrod event in disbelief, wondering how his team could have screwed up so badly. Why not just hold the press conference inside the capitol, in a conference room, someplace where the Romney backers couldn’t intervene?

Obama went looking for someone to yell at. He found Dan Pfeiffer. How could this event, he wanted to know, this simplest of exercises, so routine a professional political operative could have designed it in his sleep, have turned into such a mess? Obama chewed out David Plouffe in the same manner.

A few days later, Obama told his senior advisors they needed to shape up. He made clear that they had to tighten their game, that the campaign had been signaling its plays before the snap. Shape up, Obama told his team, and do it now.

From that moment on, Plouffe and Messina would work together much more closely, excluding others (including Cutter) who were filling vacuums that were being ignored by the White House, with Plouffe becoming the final word on messaging: it meant deciding what issue they would focus on, what they were going to say about that issue on a given day, and who was going to say it. To make sure the campaign’s two outposts—the headquarters in Chicago and the White House—were on the same page, Pfeiffer began traveling to Chicago on a regular basis, spending a day or two a week working out of the campaign office.

“The thing that was missing,” Pfeiffer said later, “was the discipline. Who’s making sure the consultants don’t talk to reporters on background? Who’s the one who’s making the decision that we’re not doing every interview that everyone wants to do?” Still, the fundamental plan that Plouffe and Messina had charted from the beginning stayed intact: they would begin the campaign with a relentless focus on Romney’s record. They would use the Democratic convention, in Charlotte in September, to make the positive case for a second term. And they would contrast those two visions during the home stretch, the two-month sprint between Labor Day and Election Day.

In 2004, John Kerry had accepted public matching funds, which meant he had only $75 million24 to spend on advertising between the time he accepted the Democratic nomination, on July 29, and Election Day. George W. Bush would formally accept the Republican nomination more than a month later, on September 2, which allowed him to spend money he had raised for the primaries up until the first week of September before dipping into his own $75 million in public financing.

In 2004, $75 million was still thought of as a lot of money for a three-month campaign sprint. (By 2012, $75 million was about the average amount the campaigns and Super PACs spent on TV advertising in a given week. The acceleration of campaign spending on the presidential level is bordering on unsustainable.) To husband those resources, and because Kerry would have to spread his money over a longer period than Bush, Kerry’s campaign didn’t advertise during August. But the airwaves weren’t completely free of political ads. One group, dubbed the Swift Boat Veterans for Truth, spent a comparatively paltry sum—about $2 million25—on spots that attacked Kerry’s service record during the Vietnam War. The misleading ads had attacked the very foundation on which Kerry was building his campaign. He hadn’t responded beyond issuing press releases, and the ads took a heavy political toll.

Messina faced the very real prospect that several groups were promising to spend hundreds of times more than the Swift Boat Veterans, and he was determined not to make the same mistake Kerry’s team had made; every attack would be answered, in one form or another, even if the campaign couldn’t spend as much as the outside groups. And indeed, the Obama campaign’s very first advertisement, way back in January 2012, was not some glossy “why he’s running again” spot; it was instead a negative ad, a response to one funded by the Koch brothers. In hindsight, this simple fact is truly symbolic of just how negative the 2012 campaign was. To think that the first TV ad aired by the sitting president of the United States running for re-election was a negative response ad to a Super PAC! When the campaign financing system someday comes completely undone (if it hasn’t already), this moment will be among the seminal bullet points tracking this downward trajectory.

But spending money early also meant, if Messina’s conservative estimates were right and the enthusiasm Democratic donors exhibited in 2008 never materialized in 2012, that the Obama team might wake up one morning in late September or early October and realize they were out of money. They could keep their advertising reservations until the last minute, but there might come a time when they would have to cancel them en masse simply because they could no longer afford them. Or they could limit advertising to the most competitive states, something Al Gore was forced to do in 2000 when he pulled out of Ohio—of all places—because he was out of cash.

On May 26, during a weekly senior advisors’ meeting with the president, Messina laid out his plan: take the risk and spend money early, either to paint an unflattering portrait of Romney or to defend against attacks from outside groups. Plouffe and Axelrod agreed with Messina’s strategy. Obama signed off, knowing full well that there was a real danger he could find himself buried by Romney’s late spending in the crucial final stretch.

“We… kind of gambled on the front end and front-loaded our media, without any guarantee that we were going to be able to make it up on the back end,” Axelrod said later, at a postelection conference at Harvard University.26 Of course, had they been out of money in October, it would have been a sign that the Obama campaign had lost the confidence of its supporters anyway.

June and July were nerve-wracking. Rove’s Crossroads organization spent a few million a week across battleground states, while Koch brothers–affiliated groups occasionally dropped in their own ad buys. But the hammer never really came down as the Obama team expected. Sure, a lot of money was spent by outside groups, but it was somewhat sporadic and never carried a cohesive message—a complaint the Romney campaign would quietly be making to reporters in an effort to publicly shame the GOP outside groups into doing a better job on messaging.

What’s more, Federal Communications Commission rules allow candidates to pay a lower rate for advertisements than noncandidate outside groups. That meant the campaigns would pay the lowest available rate, while outside groups, car dealerships, furniture stores—any other entity trying to purchase television time—were paying the market rate. So even though it was being outspent on the air, the Obama campaign was actually running more individual advertisements than the various Republican and conservative outside groups were. And Romney’s campaign was waiting until the last minute to place their TV buys, costing them more on the front end. This was a fine way to buy ads for, say, toothpaste, since you’d be advertising toothpaste for years to come and could take full advantage of the eventual refund. But since campaigns have a specific end date, this was not the best way to husband resources. All the buys the Obama campaign made were done weeks or even months in advance, which is the cheapest way to guarantee the best time slots—a seemingly small but strategic way the Obama campaign outperformed Romney’s.

The number of available ad spaces was finite, and the supply didn’t increase in response to demand; people didn’t go out and start new television stations just to capture the candidates’ advertising dollars. About the only way new TV ad space was created was if local stations decided to shorten their newscasts from twenty-two minutes to twenty or even eighteen minutes, which gave their ad sales teams two to four more minutes to sell. Thus competition for the small number of slots was fierce, and prices kept rising. By the end of the campaign, ads in the Washington, D.C., media market, which would reach crucial swing voters in the northern Virginia suburbs, were as expensive as advertisements were in New York City, the nation’s priciest media market. Demand was so great that ads that reached swing voters in markets like Las Vegas, Denver, Tampa, and Orlando ended up costing four, five, even six times the regular rate—but again, candidates are to a point exempt from this inflation, which is mostly intended for the protection of the local congressional or state senate candidates trying to get their message out, not presidential campaigns.

Despite the gamble of spending early, the Obama campaign maintained the reservations it had already made for September and October and locked in those cheaper rates. Not thinking about those rates was one of the Romney campaign’s worst strategic blunders. It was as if his team was more worried about ad agency and consultant fees than about making sure they could afford to advertise, let alone reserving slots when they would most need them.

The disparity in ad buying highlights an area in which Obama’s campaign excelled: planning ahead. To be sure, Team Obama made some mistakes—witness Boston. But those were exceptions. Not only was the team particularly good at preparation; Romney’s campaign was fantastically bad at long-term planning. In terms of TV ad buying, Romney’s team was using a playbook from the ’90s, while Obama’s team was writing an entirely new one.

The Obama campaign had mapped out their reactions to just about every possible contingency well in advance. While waiting for the Supreme Court’s decision on the constitutionality of the individual mandate in the health care law, Stephanie Cutter and Jennifer Palmieri (a real professional and a Clinton White House veteran brought in as deputy White House communications director in 2011 in an attempt to repair relations with the White House press corps) had created so many reaction plans for the various scenarios that they ended up filling a binder. “The only thing we didn’t have planned out was, like, a nuclear war,” Cutter joked later. The White House even had a legislative alternative ready to go had the Court ruled against it, and a carrot to entice the states to establish health care exchanges, and a mandate, on their own.

The case before the Supreme Court was actually an argument that had begun on the fringes: that the mandate was unconstitutional because the government couldn’t penalize someone for not participating in commerce. While the argument started on the fringes, it took off in the conservative grass roots, and many Republican attorneys general decided to sign on. There were a few other cases challenging different aspects of the law for which some judges had found in favor, so the Supreme Court consolidated all of them into one case. But the central focus was on the mandate. The Obama White House maintained that under the commerce clause, it did have the right to force people to buy a product or face a penalty. There was enough precedent for using the commerce clause that many in the legal community assumed it would win its case rather easily. Well, the White House won it, but not the way it had expected. It came as an extraordinary relief to the West Wing when the Court, in a strange 5–4 decision authored by Chief Justice John Roberts, ruled in favor of the mandate by declaring it a tax, which was consistent with Congress’s powers to levy fees, at the same time implying, however, that Congress did not have the power to do this under the commerce clause—a significant decision in its own right.

Obama had always been confident that his health care law would pass constitutional muster. Privately, he and his legal people were convinced the law would survive 6–3, believing they would win Anthony Kennedy—the usual swing vote on the Court of late—and Roberts. And if they won 5–4, they assumed it would be Kennedy who would give them their fifth vote.

What no one in the White House imagined was that John Roberts would be the swing vote, especially if it was clear that conservatives had won Kennedy over.

Just how this actually went down inside the Court is something the public won’t know for sure for decades, when the internal deliberations and the papers of retired or deceased justices finally become public, which is at the discretion of each justice. (For instance, Justice Byron “Whizzer” White allowed his papers to be made public ten years after his death.) What is clear is that Roberts was inclined to strike down the law; he had assigned himself the opinion, knowing it was going to be a legacy maker for his Court no matter which side he ended up on. It was during his deliberations—which included some subtle lobbying by fellow justice Stephen Breyer—that he concluded that just because he didn’t like the law didn’t mean it wasn’t constitutional, and that overturning it would be a form of judicial activism that Roberts was predisposed against. One thing many Court observers have learned about Roberts is that at the end of the day, he’s an institutionalist, meaning he believes if you do plan to set new precedents, you should do so gradually, respecting the other two branches of government along the way—hence ruling in favor of the health care law but curbing the expansion of the commerce clause.

The decision was a massive blow to Obamacare opponents. While Team Obama is convinced that they could have survived a summer of questions surrounding the constitutionality of the health care law had it been struck down, the campaign would likely have looked a lot different. For one thing, it would have given Romney more credibility on the issue of health care when he claimed what was right for Massachusetts wasn’t necessarily right for the country as a whole. And, of course, it would have meant that the health care issue, something the Obama campaign hoped to essentially ignore for the duration of the re-election phase, would have been front and center. No way could they have devoted weeks or months to discrediting Romney; instead, they would have had to spend weeks defending a new health care fix, one unlikely to ever pass muster with a Republican House. In short, John Roberts saved the Obama campaign.

And so, the last element Barack Obama needed was a case for a second term.

For a candidate who desperately needed voters to consider whether they would be better off after another four years rather than whether they were better off than they had been, Obama had been remarkably defensive about his first-term agenda. And to some degree, circumstances—like the Court’s decision to take up the health care law in the first place—required such a defense. But voters still needed to hear what would come next, why they would be better off with another four years of Barack Obama.

The venue in which to make that case would be the convention, set for the first week of September in North Carolina.

Obama’s team had watched with barely concealed glee as Republicans had all but wasted their own convention. A hurricane had barreled through the Caribbean and up Florida’s Gulf coast, barely missing Tampa, where Republican delegates had gathered, and forcing organizers—for the second time in four years—to cancel the first day of events.

On the second day Ann Romney gave a moving, heartfelt speech that helped humanize her stiff and at times standoffish husband, but just minutes later Chris Christie, governor of New Jersey and one of the party’s rising stars, delivered a keynote address focused almost entirely on himself and his own record rather than on his party or its presidential nominee. Christie and Ann were not supposed to speak on the same night, but events dictated that the two would have to share their prime-time hours. Ann’s remarks ran a tad long, and to save time the Republican Party’s executive producer for the convention informed Christie’s folks that they would have to kill his introductory video. That did not go over well with the New Jersey governor. According to some eyewitnesses backstage, Christie used some version of the f-bomb and implied that if the video didn’t play, he wouldn’t speak. It was a potential disaster. In order to avoid a scene the video was aired, which created an awkward interlude between Ann and Christie. To make matters worse, and to the eternal befuddlement of Team Romney, Christie never praised or even acknowledged Ann for her remarks before jumping into his self-promotion. Christie’s not mentioning Romney by name became a thing on Twitter. Finally, after about fifteen minutes into his speech, Christie did talk about Mitt, but the damage was done.

The next night (technically day three), Paul Ryan gave a speech riddled with factual inaccuracies. Day four was the Romney campaign’s final opportunity to sell millions of Americans on their plan without having to deal with a media filter. The final hour, which was to include Romney’s acceptance speech, was instead dominated by one of the odder moments in recent political memory: actor Clint Eastwood made a surprise appearance, and then for twelve awkward, surreal minutes he lectured an empty chair—which he said stood in for President Obama. Romney advisors were horrified. They had wasted a dozen of the most valuable minutes of the entire campaign, when the eyes of the nation were on them, and had just guaranteed that the talk of the media and the bandwidth of YouTube would make their candidate look like a fool.

The irony of all this was that two of the three broadcast networks—CBS and NBC—had asked the Romney campaign whether they wanted to play their candidate’s campaign video in the 10 p.m. hour as the introduction to Romney’s speech. The networks had done this for every nominee of both parties going back twenty years. But the Romney team decided instead to claim the 9 p.m. hour, when only the cable networks were airing the convention. Featuring a series of testimonials from people who had worked for Romney over the years, the video did what the campaign had failed to do for months before the convention, which was humanize the sometimes-stiff Republican nominee. It was probably the best case for Romney the person that anyone had ever seen—but alas, only those watching cable saw it, and they were the diehards of both parties, whose minds were already made up. The swing voters who would watch in the 10 p.m. hour, when every broadcast network cut in, instead saw a cranky old man yelling at an empty chair.

Marco Rubio, the popular young Florida senator who was already a rising star in the party, gave his own well-received speech after the weird Eastwood deal. But after Eastwood’s rambling talk, Romney’s acceptance speech ran well past the planned 11 p.m. cutoff. Most news stations delayed their local news broadcasts to continue airing the speech, but the later the hour, the more likely viewers were to turn off the set (or, in the case of some, fall asleep in their chairs).

Romney’s address was surprisingly personal for a man not known for sharing his feelings. But the following day, as feared, almost every major news outlet mentioned Eastwood’s bizarre speech in their coverage of Romney.

The Republican convention was the Romney campaign in a nutshell—poorly planned, too gimmicky, and off message.

The Obama team exerted much tighter control on their convention. They edited speeches line by line, strictly regulated the time each speaker was allowed at the podium, and even managed that most difficult task of convention organizers—allotting speaking time to candidates who might try to succeed Obama four years down the road, like Maryland governor Martin O’Malley and Montana governor Brian Schweitzer, in a manner that kept everyone relatively happy.

The only speech the Obama team left largely up to its author demonstrated just how far one of the most fascinating relationships in American politics had come. By now, Axelrod and Bill Clinton had grown to deeply respect each other even if there were still sore feelings. Clinton’s speech-writing process had always been frenetic, marked by last-minute revisions and handwritten edits; this time around, in the days before his convention address, Clinton actually called Axelrod for help. (Even after it had been edited down to 3,000 words, Clinton added another 2,000 extemporaneously.27 When he would go off script, the teleprompter operator would scroll up and down, frantically looking for the section Clinton was reading—or, more accurately, ad-libbing.)

Clinton’s speech stood in stark contrast to Eastwood’s bizarre rant the week before in Tampa. Despite some physical signs that the former president was slowing down (and close watchers of the man say they are more pronounced than casual watchers might notice), he was on his game when the lights came on. Bill Clinton demonstrated again his ability to connect national issues with an individual voter’s situation, in a manner that resonates. “If you want a ‘you’re-on-your-own, winner-take-all’ society, you should support the Republican ticket,” he said. “If you want a country of shared prosperity and shared responsibility, [a] ‘we’re-all-in-this-together’ society, you should vote for Barack Obama and Joe Biden.”28

The former president neatly summed up the sluggish economic recovery, what Obama had accomplished in his first term, and the contrast between Obama and Romney better in a single address than Obama had been able to do in his four years in office. Clinton’s speech was a much bigger hit, and arguably made a bigger postconvention splash, than the one Obama gave the next night. What really made Obama jealous was not that Clinton stole the show, it was how he did it—with an incredibly wonky, long, and sometimes rambling address. Obama so desperately wanted to wonk out more, ramble more like a professor, but when he did it, it didn’t work. Maybe it’s the southern part of Clinton, the preacherlike qualities that make his audiences more patient.

The Democratic convention was not without its unscripted flubs. The enthusiasm gap Democrats now faced meant they wouldn’t be able to re-create the high-intensity acceptance speech Obama had given four years earlier, in Denver, when his supporters had packed Mile High Stadium to cheer him on. Convention organizers had planned to duplicate that crowd in Bank of America Stadium, home of the Carolina Panthers, but they scrubbed that venue when it became clear they wouldn’t be able to give away enough tickets to fill the seats. Still, they didn’t want to look as if they were scrubbing the outdoor speech because of a ticket issue, so the organizers were praying for rain. And they got just enough of a storm passing through the area that they were able to make the decision seem to be due solely to the weather. There really was a storm headed to Charlotte on Thursday, but it wasn’t nearly as dire as organizers pretended to fear; it was just enough for them to look overly cautious. When Obama took the stage that night, there was hardly a cloud in the Charlotte sky.

There was one other blip. Reporters scrutinizing a draft of the party platform noticed that it failed to include a reference to God, and that it eliminated language used four years earlier, when it specifically identified Jerusalem as the capital of Israel.

The White House had been asked to vet the platform before it went to the committee. Denis McDonough and Ben Rhodes, the two most political members of the national security team, had signed off on the Israel language, which they had changed to reflect current U.S. policy. Both put accuracy above what made political sense, and calling Jerusalem the capital is important to many voters, including those in the swing state of Florida. Patrick Gaspard, the former White House political director who left to become executive director of the Democratic National Committee, swears he drafted but never sent an e-mail to the platform committee reminding them to keep references to God and faith in the document. There was no overarching reason why he didn’t send it; he simply forgot.

Obama blamed Gaspard for the screwup. “Patrick, I have two vulnerabilities—Israel and faith,” Obama said. “And we botched both.”

Gaspard moved fast to fix the problem. The platform would be amended from the floor of the convention, with the assistance of convention chairman Antonio Villaraigosa, then the mayor of Los Angeles and perhaps the highest-profile Hispanic in the Democratic Party at the time. Villaraigosa would call for a vote on the new language, then rule in favor of the changes no matter how many liberals voted no. “I got this,” Villaraigosa told Gaspard. “I know how to call a vote.” There were audible boos over the change, but Villaraigosa rammed it through—crisis averted, at least with the mainstream media; conservative news outlets were having a field day, but at this point in the campaign, the Obama folks didn’t worry much about right-wing outrage.

Obama addressed delegates the following night, offering a delicate balance between a defense of his first term and a forward-looking vision for the future. “I won’t pretend the path I’m offering is quick or easy; I never have,” Obama said. “You didn’t elect me to tell you what you wanted to hear. You elected me to tell you the truth. And the truth is, it will take more than a few years for us to solve challenges that have built up over decades.

“Our problems can be solved. Our challenges can be met. The path we offer may be harder, but it leads to a better place. And I’m asking you to choose that future,” he said. That path included more policy in a single speech than Obama had offered during the rest of the campaign, but it wasn’t anything revolutionary. Pledges included one million new manufacturing jobs and a $4 trillion cut in the deficit—the jobs number was something the economic recovery should automatically take care of; the deficit cut was a pledge Republicans were going to try to make him keep regardless of whether he pushed for it or not. But the real message Obama intended to send was that the election offered a stark choice between his plan and the conservative alternative. Gone were the references to Romney the flip-flopper; instead, Obama made clear, it was right versus left. It was time to make this a “choice” election.

As a measure of just how polarized the electorate had become, neither Romney nor Obama received much benefit from either the Tampa or Charlotte event; the proverbial convention bounce in the polls never materialized, because so many voters had already made up their minds.* Nevertheless, the lack of a bounce hurt Romney more than it did Obama. In the first surveys conducted after the conventions, every news organization in America found the same results: Obama was ahead. Even Rasmussen, the autodial polling firm whose methods had been criticized for including too many Republican voters in order to guarantee the best possible GOP spin on a matchup, showed Obama leading by five points. Polling in virtually every swing state showed the same trends: in the week following the convention, Obama led Romney in Ohio by four to seven points and in Virginia by five to eight points. Similar margins showed up in surveys conducted in Iowa, Nevada, New Hampshire—almost every swing state. Even polls in Florida, a state Republicans believed they could put away early, showed a competitive race, with results ranging from an NBC/Wall Street Journal poll showing Obama leading by five to a Republican firm’s poll showing Romney leading by three.

Romney, it was clear, was running out of time to change the equation. He would have only three chances—the presidential debates.

Obama saw the same polls. A year earlier, after the fight over raising the debt ceiling, his job approval number had been toxically mired in the 40s. Now, as Obama retreated to a less-than-swanky resort at Lake Las Vegas, a half-hour drive from the glitz and glamour of the Strip, to spend a few days preparing for his first face-to-face encounter with Romney, his cockiness showed through even the thick veil the campaign had put between their candidate and the press. Instead of spending quiet time studying the issues and his opponent’s likely positions, Obama attended a rally of Nevada supporters. A few days later, he visited the Hoover Dam. During a stop at a campaign office, where he dropped in to thank volunteers with a pile of six pizzas, he said preparing for debates “is a drag.” “They’re making me do my homework,” he told one volunteer. “Basically, they’re keeping me indoors all the time.”29 Obviously, he was trying to show that he was keeping his cool, but he was doing nothing, even halfheartedly, to frame the challenge ahead of him. The fact of the matter was, Obama didn’t view Romney as a really worthy opponent. Little comments like the one to Nevada campaign workers were telling.

There is always a blurry line when candidates discuss debate prep: how much work do you want to admit having to do? After all, you’ve been telling the public how obviously wrong your opponent’s proposals are, so why do you need to review those arguments? And it’s certainly expected that you know your own positions. Yet Obama’s comments carried a tone that went beyond joke or spin, and right into arrogance. His was hardly the attitude of someone throwing himself full-bore into the rigors of preparation.

Behind closed doors, Obama had been similarly dismissive. Presidents running for re-election frequently find themselves in an odd position when they debate their opponents. For several years, they have been unchallenged in person; no one is the president’s equal, and the Seal of the President of the United States lends a kind of protective shield that elevates one man above all others. But when presidents land on a debate stage, they face a person who will be treated as their equal, at least by the moderators. For the first time in a very long time, someone can actually tell the president of the United States to stop talking.

In 2008, Obama may not have particularly liked John McCain, but he respected the Arizona Republican and thought him worthy of the presidency. In 2012, Obama had come to personally dislike Mitt Romney on a much deeper level. (This is apparently not an unusual occurrence for Romney; McCain and his fellow Republican candidates came to feel the same way about Romney during the 2008 primaries.) Obama’s feelings toward Romney, he later acknowledged to his closest advisors, had blinded him to the former Massachusetts governor’s strengths and led him to underestimate his opponent.30

On October 3, the two men met at the University of Denver for their first debate, and Obama’s lack of preparation showed almost immediately. He missed his cues and flubbed some lines, as if he had been asked questions he didn’t anticipate. But the questions that seemed to trip Obama up the most were ones his advisors had anticipated and prepared for—the health care reform law, for example.

Watching from another room, Obama’s top advisors saw with a growing sense of horror their candidate flailing about. Focus groups were showing new enthusiasm for Romney; thanks to high-tech dial monitoring of undecided voters across the country, Obama advisors could feel their lead—stable but slim—slipping away in real time. The split-screen broadcast, which kept cameras focused on both candidates no matter who was answering a question, showed a shifty-eyed Obama visibly disgusted with the more poised, calm, and polished Republican. Several top advisors who had been buoyed by predebate polls felt their stomachs sink: their guy might have just blown the election.

Across the hall, in the room reserved for Romney advisors, the mood was incredulous. Here was their candidate, a stiff, distant businessman, beating up on one of the most practiced and talented politicians of his generation. In Boston, Romney’s communications director, Gail Gitcho, had to warn her surrogates not to pound their chests or declare victory too loudly.31

As Obama walked offstage after declaring it “a terrific debate,” he knew he had screwed up. Twenty years before that evening he had married Michelle Robinson, and his staff had planned an anniversary celebration at Obama’s hotel later that night. But the party was subdued at best. Obama spent the rest of the evening and the following morning on the phone with his biggest supporters, apologizing for his lousy performance.

The next morning, Obama needed a pick-me-up. On debate day, the weather in Denver had been gorgeous; temperatures reached the mid-70s. But the morning after, when the campaign had scheduled a rally at the city’s Sloan’s Lake Park, the mercury had plummeted to the 40s.32 Still, the park was packed, and people in the crowd started shouting when Obama got to the stage: “We got your back!”

Obama was moved, and so was his staff, even though many of that evening’s newscasts ran interviews with those supporters, all of them concerned about the president’s debate performance.

In the next two debates Obama was sharper. He contrasted himself with Romney at almost every turn, negotiating a delicate line between being critical and sounding mean. And even though the focus groups had rendered a terrifying verdict in Denver, one thing didn’t change: the poll numbers. Obama’s campaign still showed their man ahead and their coalition ready to turn out to vote.

On Monday, November 5, Barack Obama attended his last-ever campaign rally as a candidate. At two minutes to 10 p.m., Michelle Obama walked out onstage at the intersection of East Fourth and East Locust Streets in Des Moines, Iowa, in the heart of the state that had launched his presidential ambitions. The president joined her a few minutes later, at times tearing up as his campaign journey came to an end.

“I came back to ask you to help us finish what we started because this is where our movement for change began,” Obama said. “To all of you who’ve lived and breathed the hard work of change: I want to thank you. You took this campaign and made it your own.”

At 10:35, Obama asked God to bless the United States of America. Two hours and fourteen minutes later, Marine One touched down at a landing zone just a few blocks from Obama’s Hyde Park home in Chicago.

On Election Day, Obama woke up in his own bed, as he had done so rarely during his first term in office. He sat for television interviews with ten local news channels that reached seven key swing states—Iowa, Wisconsin, Ohio, Florida, Virginia, Colorado, and Nevada.

He played basketball with some of his closest friends: education secretary Arne Duncan, his body man Reggie Love, Marty Nesbitt, and Mike Ramos, a friend from Obama’s high school days in Hawaii. Michelle’s brother, Craig Robinson, White House chef Sam Kass, and Chicago Bulls legend Scottie Pippen were also on the court.33

All along, Republicans had assumed that there was no way that African American and Hispanic voters would turn out at the same levels they had in 2008, though they would certainly make up a larger part of the electorate than they had in 2010. Moreover youth turnout would be down; the trend of union households losing market share would continue; and independents would give Romney much more support than they had given McCain four years earlier.

Those assumptions flew in the face of historical precedent, which showed the share of white voters in the electorate declining every four years. But, the logic went, the Obama campaign in 2008 had expanded the electorate so much that it couldn’t expand any further.

In essence, the Romney campaign was giving the 2008 Obama campaign more credit than it deserved. And they were wrong. Black voters turned out at a higher level than they had in 2008; for the first time in American history, a larger percentage of black voters cast a ballot than did white voters. Hispanic voters showed up in greater numbers, too, and more important, they actually voted for Obama in higher proportions than they had four years earlier. Self-described independents had given Romney 50 percent of the vote, compared with 45 percent for Obama, but those who called themselves moderates—a whopping 41 percent of the electorate—had given Obama a fifteen-point edge. It turns out quite a few self-described independents were ex-Republicans, right-leaning voters who did not want to identify with their former political party.

What surprised the Obama campaign most was younger voters: those between the ages of eighteen and twenty-nine, a segment that went for Obama by a 60 to 37 percent margin, made up 19 percent of the electorate, a slightly larger percentage than they had been in 2008. “No one—you, me, no one—thought we’d increase youth turnout,” Messina marveled.

The 2012 campaign was a far cry from Obama’s first victory, in 2008; “Hope and Change” had been replaced by “Forward.” This may have been a calculated effort to change a conversation the White House would otherwise lose, but the campaign had showcased what was vintage Obama: lofty rhetoric, a populist pitch, a cocky candidate, and, as in every Obama story, at least a few moments of back-against-the-wall panic. And ultimately, on Election Day, the president displayed his trademark preternatural cool. Obama had played basketball.

That night, as polls closed across the nation, Obama and his senior advisors watched the network broadcasts on a bank of TVs at the Fairmont Hotel. Exit surveys showed Obama running away with swing state after swing state. At 11:14, NBC was the first network to call the presidency, just fourteen minutes later than it had called the election four years earlier. It was not technically a landslide re-election, but in this political environment it was about as close as one party could get.