The Trump-Bannon partnership, like so much else in Trump’s life, has a bizarre and winding lineage that traces back to a lawsuit. In the mid-1990s, Steve Wynn, the Las Vegas casino mogul, was looking to move in on Atlantic City, New Jersey, a possibility that threatened the livelihoods of the Trump Plaza Hotel and Casino, the Trump Taj Mahal, and other gambling establishments along Atlantic City’s Boardwalk. Unable to make headway, Wynn’s Mirage Resorts, Inc., filed an antitrust suit against Trump’s company and Hilton Hotels, setting the stage for an epic showdown. At the time, Trump and Wynn were both in their fifties, both graduates of the University of Pennsylvania, both fiercely competitive giants of the casino industry, possessed of healthy egos, and operating at the peak of their powers. And perhaps because they shared so much in common, they were bitter enemies. “They hate each other’s guts,” a casino analyst told the Philadelphia Inquirer. “It’s like poison.”
Right away, things had gotten very strange. A private investigator working for Trump’s defense team had gone off to dig up dirt on Wynn and Mirage, only to switch allegiances partway through his assignment and secretly defect to his target. The resourceful sleuth—whose tradecraft included using a “modified jock strap” with a hidden tape recorder and microphones concealed in a belt—turned over to Wynn the secrets he had purloined for Trump, later claiming that he was moved to do so by a crisis of conscience (and not, as Trump’s lawyers suggested, a $10,000-a-month consulting deal with Mirage).
Wynn and Mirage sued again, this time claiming that Trump’s company had engaged in a conspiracy to steal its trade secrets—including a list of high-rolling Korean gamblers about whom, Wynn’s suit alleged, it spread dark rumors of money laundering and mob ties, in hopes that Wynn Resorts would be denied a New Jersey casino license. (The lawsuit revealed, among many other colorful details, that the investigator had given his counterintelligence mission the code name “Operation Seoul Train.”) An attorney for Trump likened the investigator, not unreasonably, to Judas Iscariot. Wynn shot back that the case exemplified “the most outrageous misconduct, the most flagrant violations of law and decent behavior in the history of the resort hotel industry.”
It was all about to explode into open court—until, on February 23, 2000, the case was abruptly settled. A week later, the reason became clear: MGM made an offer to buy Mirage Resorts that eventually netted Wynn, its largest shareholder, around $300 million. Wynn’s designs to build a casino in Atlantic City never came to fruition. In the aftermath, with both men having effectively “won” their battle, Trump and Wynn became friends.
And that is how, several years later, at a fund-raiser for Children’s National Medical Center in Washington, D.C., Steve Wynn called his friend Donald Trump over and introduced him to a man who would soon set the course for his unlikely political rise: David Bossie.
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By the time he met Trump in the late 2000s, Bossie, then still in his early forties, was already a hardened veteran of Washington’s political wars. Smitten with Ronald Reagan as a teenager growing up in Boston, he became youth director of Bob Dole’s 1988 presidential campaign, and then a foot soldier in Newt Gingrich’s Republican revolution when the GOP took back the House of Representatives in the 1994 election. Not long afterward, the beefy, buzz-cut, hyperintense Bossie (who still resembles a Dick Tracy villain) landed a job as chief investigator for the House Government Reform and Oversight Committee.
The job put Bossie at the beating heart of the Republican anti-Clinton movement that was then still picking up steam, and in the employ of perhaps its fiercest prosecutor, Representative Dan Burton of Indiana, the committee’s new chairman. Even before Burton took the gavel in 1997, his unhinged zeal to take down Bill Clinton was the stuff of legend. A few years earlier, convinced that the 1993 suicide of Clinton’s deputy White House counselor, Vincent Foster, was in fact a cold-blooded murder, Burton had re-created the event by shooting a watermelon with a pistol in his backyard in an effort to prove his theory. (He didn’t convince too many people, but he did earn the enduring nickname “Watermelon Dan.”)
When he became Oversight chairman, Burton quickly laid waste to the committee’s tradition of august bipartisan restraint and seized on its considerable legal powers—in particular, the power to issue subpoenas—to torment the Clintons, often by dispatching his chief investigator to hound anyone he suspected of abetting them.
Bossie required no special encouragement. He routinely evinced a zealousness that matched, or even eclipsed, that of his boss. The New York Times once described him, in a news story, as “a relentless ferret.” He cut a strange figure. A volunteer firefighter, he lived in a firehouse in Burtonsville, Maryland, where he slept in a bunk bed and responded to emergency calls when he wasn’t racing off in pursuit of real and imagined Clinton perfidies. But some of those Clinton scandals were legitimate. And Bossie, who was often first to document them, was a favorite source of political reporters, to whom he reliably leaked the latest incriminating details about the first family—even if his methods rubbed some of his own colleagues the wrong way. Not long after Bossie’s arrival, the Oversight Committee’s counsel abruptly quit, blast-faxing to reporters a letter of resignation that attacked “the unrelenting self-promoting actions of the Committee’s Investigative Coordinator.”
Relentlessness and self-promotion were no sins in Gingrich’s Washington. But Bossie’s fanatical desire to fell the Clintons at any cost eventually did him in. Burton’s committee developed a troubling reckless streak that led to unconscionable errors. In their determination to prove that Clinton was illegally taking money from Chinese donors, Burton’s staff fired off hundreds of subpoenas, sometimes targeting the wrong person. In 1997, for instance, his investigators mistakenly subpoenaed the telephone and financial records of an elderly Georgetown University professor named Chi Wang, who happened to share a name with a major Democratic donor, and yet, when Bossie was apprised of the error, he still wouldn’t relent. “Whether he deserves a subpoena or not, we haven’t decided,” he said of the innocent professor. “If you make a mistake—and we’re not sure we made one—you want to look into it.”
But it was Bossie’s recklessness in a different Clinton investigation—this one involving the jailed former White House associate attorney general Webster Hubbell, once a partner at Hillary Clinton’s Little Rock, Arkansas, law firm—that finally brought about his downfall. In 1998, Burton released some transcripts of prison recordings of Hubbell’s private telephone conversations. (Hubbell had been convicted of fraudulently billing his law firm.) Burton went on Nightline and Meet the Press to announce that the conversations implicated Clinton herself in the fraud. The media, by now conditioned to tout Burton’s charges, went into overdrive on what looked to be a major new scandal. Burton didn’t know it, but he was about to walk into a trap.
His Democratic counterpart on the Oversight Committee, Henry Waxman of California, was a legendary investigator himself, with a clever and sharp-eyed staff alert to Bossie’s recklessness. (At the time, Waxman’s Oversight investigation of the tobacco industry was being made into the Oscar-nominated Al Pacino–Russell Crowe film The Insider.) While conducting its own forensic examination of the Hubbell transcripts, Waxman’s team discovered that the excerpts Burton had released to the press had been doctored in such a way as to appear to incriminate Clinton, when the full transcript plainly did not. They had a good idea of who the culprit was.
Rather than simply issue a press release, Waxman devised something far more attention-grabbing and dramatic. The following Sunday, Burton was booked for an encore appearance on Meet the Press. The show’s host, Tim Russert, was quietly made aware of the discrepancy between the two sets of Hubbell transcripts.* On Sunday, when the cameras began rolling, Burton became an unwitting captive as Russert, the dean of Washington journalism and a maestro of the prosecutorial interview, confronted the chairman on air with evidence of the doctored transcripts.
The uproar was immediate and intense. Gingrich, humiliated, condemned Burton’s committee as “the circus.” Republicans fumed at the embarrassment Burton had brought on them and demanded he atone for it. The Washington Post splashed the story across its front page: “Burton Apologizes to GOP.” The whole edifice of probity and professionalism that Republicans had painstakingly constructed to give themselves license to go after the Clintons seemed to come crashing down at once. “The Burton investigation is going to be remembered as a case study in how not to do a congressional investigation and as a prime example of investigation as farce,” declared Norman Ornstein, a respected congressional scholar at the conservative American Enterprise Institute.
The fallout landed heaviest on Bossie, who was very publicly fired from his job. Once a feared and respected figure who operated in the innermost sanctum of Republican power, he was now cast far, far outside it, to the fringes of the conservative world. The subsequent collapse of the Republican power structure (including Gingrich’s resignation as House Speaker) brought about by the backlash to Bill Clinton’s impeachment only ratified Bossie’s status as persona non grata among respectable mainstream Republicans.
Bossie, however, did not disappear or even leave Washington, D.C. Nor did he abandon his obsession with taking down the Clintons. Instead, he became president of the conservative group Citizens United, a position that gave him rein to become what he was probably best suited to being all along: an uninhibited, full-time, generously compensated anti-Clinton warrior, whose plots and intrigues could now be funded by wealthy conservative ideologues.
The job made Bossie a big deal in a small but intense universe of rabid Clinton haters. He arrived at a pivotal moment. By and large, the public rejected what this group’s members regarded as their great triumph—Clinton’s impeachment—and punished Republicans such as Gingrich, whom they deemed responsible for it. For those who had fought so long and hard to damage Clinton, this unexpected turn of events only deepened their animosity and drove them further from the mainstream of the GOP. Their influence waned. A new Republican president, George W. Bush, got elected by championing a different, more “compassionate” conservatism, while holding the right-wing fire-breathers at bay.
Bossie’s ilk continued nursing their obsession, blasting out fund-raising appeals, making overheated political films, propagating dark conspiracy theories that revolved around the Clintons, and gathering at the sorts of conferences where intense adherents to far-right-wing causes set up tables to lure new recruits, and vendors hawk merchandise pitched to the politics of the crowd, such as Hillary Clinton nutcrackers, and bumper stickers that read “Life’s a Bitch. Don’t Vote for One.” Yet for all its fevered efforts, this group rarely made a ripple outside its own insular bubble—its members were mostly cranks who wound up speaking mainly to one another. Republican politicians were happy to receive their votes. Many, in fact, depended upon them, even as they privately held the cranks in low esteem. As one campaign manager for a Republican presidential candidate described them, “They’re the stuff you scrape off your shoes. Bad people.”
Yet in one instance the Clinton-haters did manage to break through in a big way—and Bossie was the man responsible. In 2007, in anticipation of Hillary Clinton’s run for the White House, Citizens United produced a scalding documentary film that purported to detail a thicket of nefarious Clinton scandals, although it consisted mainly of interviews with off-kilter conservative commentators such as Dick Morris and Ann Coulter maligning the former first lady. Bossie’s plan was to release Hillary: The Movie as a cable television video on demand in January 2008, just as the Democratic presidential primary was getting underway. In truth, it was more of a fund-raising ploy than a serious effort to sway Democratic voters, who would be unlikely to seek out a film attacking their leading presidential candidate, much less be turned against her by the opinions of the right-wing talk-radio hosts who were its central characters.
But Bossie didn’t get very far. The Federal Election Commission prohibited Citizens United from advertising the film on the grounds that Hillary: The Movie constituted a campaign ad. The new McCain-Feingold campaign finance law restricted so-called issue advertisements that mentioned federal candidates from airing within thirty days of a primary and sixty days of a general election. Bossie sued, claiming his film was protected commercial speech and therefore exempt from campaign laws. A three-judge panel of the U.S. District Court for the District of Columbia denied his request for an injunction, stating that his film was effectively a ninety-minute campaign ad “susceptible of no other interpretation than to inform the electorate that Senator Clinton is unfit for office, that the United States would be a dangerous place in a President Hillary Clinton world, and that viewers should vote against her.”
Yet in 2010, the Supreme Court disagreed and sided with Bossie in Citizens United v. Federal Election Commission, a landmark decision that said political spending is protected speech under the First Amendment, and corporations and other organizations can therefore spend unlimited amounts of money to support or denounce candidates in an election. Republicans were ecstatic.
The Supreme Court case briefly turned Bossie into a conservative cause célèbre, not because Republicans thought his film would have any effect on Clinton, who had already been dispatched by Obama, but because it was the vehicle that eliminated campaign spending restrictions, opening the floodgates for more corporate money to pour into electoral politics. It bestowed upon Bossie a temporary glow that made him seem like a big deal and a consequential player in Republican circles at the very moment when Donald Trump was getting serious about running for president and casting about for advice. Trump had few connections to the political world, where no one took him seriously, even though (and in part because) he was kicking up a shit storm by claiming that Obama had faked his birth certificate and wasn’t really born in the United States.
And yet Trump was hardly dissuaded. His habit always was to quiz anyone and everyone about what they thought, whether or not that person could claim any expertise on the topic at hand. In Trump’s mind, then, Steve Wynn’s opinions about politics and how to shape it were every bit as valid and worth listening to as those of a seasoned political consultant—and maybe more so because Wynn had traveled a path so similar to Trump’s own, not just in business but also in politics. Wynn, too, had once been a Democrat and even claimed to have voted for Obama in 2008. But he turned sharply against the president and the Democratic Party after the election, and would later get into a tabloid-friendly fight over the subject with the actor George Clooney, who once stormed out of Wynn’s dinner party after the casino magnate called Obama an “asshole.” For Trump, who was trying to figure out how to navigate national politics, Wynn’s imprimatur of Bossie, and Bossie’s own post–Citizens United celebrity, both counted for a lot. Trump brought Bossie into the fold, later describing him this way: “Solid. Smart. Loves politics. Knows how to win.”
By March 2011, employing a style that would soon become familiar, Trump had orchestrated the “birther” crisis over Obama’s citizenship, roiling the political world and making himself a central figure in the national conversation. Now he faced a dilemma: Wynn had invited him to be a guest at his three-day, celebrity-studded Las Vegas wedding on April 30, where Clint Eastwood was going to be the best man. But The Washington Post, eager to capitalize on Trump’s sudden political notoriety, had invited him to be a guest at the White House Correspondents’ Association dinner that was being held the same night. Trump had accepted both invitations.
In the end, he decided to attend a Friday night party in Las Vegas honoring Wynn and his fiancée, Andrea Hissom. Trump mingled poolside with Sylvester Stallone and Hugh Jackman. Then, early the next morning, he jetted off to Washington, D.C., where the comedian Seth Meyers was going to emcee the Correspondents’ Dinner. Trump had no idea that Meyers and Obama were anticipating his arrival and preparing to make him a national laughingstock. And none of them knew that this elaborate humiliation would be the catalyst that put Trump on a path to the White House.
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It was a setup from the beginning. Trump had been invited to the Correspondents’ Dinner by Lally Weymouth, the daughter of The Washington Post’s legendary publisher Katharine Graham and someone who routinely courted stars and celebrities as guests to the annual event held at the Washington Hilton. Trump’s invitation had caused grumbling in the Post newsroom. Was it really appropriate, reporters wondered, for the paper to embrace the purveyor of a racist conspiracy theory directed at the nation’s first black president—who would, not incidentally, be the dinner’s featured speaker?
But ever since 1987, when, in the wake of the Iran-Contra scandal, the journalist Michael Kelly brought one of its central figures, Fawn Hall, the document-shredding secretary to Lieutenant Colonel Oliver North, to the event, there had been an unspoken competition among prestige media outlets to land the most notorious and newsworthy guests. In the social context of elite Washington, the Post’s nabbing Trump as a guest was a coup. And Trump was, by all accounts, delighted to be among the actors, starlets, and television personalities who flock to the A-list dinner each year. Knowing that the dinner speakers typically single out members of the audience for roasting, and that Trump was a ripe target, a couple of Post reporters asked him if he was prepared for some ribbing. Trump waved them off. “I’m fine with this stuff,” he replied.
Trump was seated in the very center of the Hilton ballroom, his confection of blond hair aglow in the bright lights, his star wattage eclipsing the graying eminences of journalism and politics who craned their necks to get a look at him. No one confronted him about his outrageous slander or questioned why he was so intent on humiliating Obama, because doing so would have run counter to the spirit of the evening. Instead, Trump schmoozed and flattered his fellow guests, and they in turn schmoozed and flattered him.
Nobody knew it yet, but the president and his staff would not be so solicitous. They had, in fact, been eagerly awaiting Trump’s arrival in Washington from the moment the news became public, recognizing the occasion as the perfect opportunity to exact a humiliating revenge. Obama’s writing staff even brought in a ringer, the comedian and director Judd Apatow, to help its most comedically gifted speechwriter, Jon Lovett, compose a devastating takedown of Trump. The White House Office of Digital Strategy had agreed to produce a video complement.
Toward the end of the evening, when the lights dimmed for Obama’s remarks, giant screens throughout the ballroom broadcast a blaring music video of Rick Derringer’s cheesy rock anthem “Real American” that the digital-strategy team had crammed full of over-the-top patriotic imagery—rippling American flags, screaming eagles, Uncle Sam—and then Obama’s long-form birth certificate came dancing across the screen. The White House had just released it three days earlier, after months of Trump’s haranguing suggestion that Obama couldn’t produce it because he hadn’t really been born in Hawaii.
As the lights came up, Obama stood at the lectern grinning broadly and looking right at Trump. “My fellow Americans, Mahalo!” he said. “As some of you heard, the State of Hawaii released my official long-form birth certificate. Hopefully this puts all doubts to rest. But just in case there are any lingering questions, tonight I’m prepared to go a step further. Tonight, I am releasing my official birth video.”
Now the screens showed a clip of Disney’s The Lion King bearing a time stamp that read August 4, 1961—Obama’s birthday. The crowd hooted and laughed.
“Donald Trump is here tonight,” the president announced. “Now, I know he’s taken some flack lately. But no one is happier, no one is prouder to put this birth certificate matter to rest than the Donald. And that’s because he can finally get back to focusing on the issues that matter, like . . . Did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”
The crowd laughed louder. Trump sat frozen in a rictus grin.
Obama kept after him: “All kidding aside, obviously we all know about your credentials and breadth of experience, um . . .” Here Obama paused to let the laughter die down. “No, seriously, just recently, in an episode of Celebrity Apprentice, at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks. There was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership, and so ultimately you didn’t blame Lil Jon or Meat Loaf—you fired Gary Busey.”
Obama started cracking up, but kept on going: “These are the kinds of decisions that would keep me up at night.” The crowd roared. “Well handled, sir! Well handled.”
Meyers was up next. After methodically working through the field of 2012 Republican presidential hopefuls, he arrived at his real target. “And then, of course, there’s Donald Trump,” Meyers said, with a devilish grin. “Donald Trump has been saying that he will run for president as a Republican—which is surprising, because I just assumed that he was running as a joke.”
Trump reddened.
“Donald Trump often appears on Fox,” Meyers continued, “which is ironic, because a fox often appears on Donald Trump’s head. If you’re at the Washington Post table with Trump and can’t finish your entrée, don’t worry: the fox will eat it.”
More laughter.
“Gary Busey said recently that Donald Trump would make a great president. Of course, he said the same thing about an old, rusty birdcage he found.”
Gone from Trump’s visage was any pretense that he was enjoying this. He did not seem to possess the ability to laugh at himself, nor even the politician’s ability to smile broadly and pretend to. Trump was plainly humiliated—and it showed.
When Meyers was finished with him, Trump, looking shaken, beat a hasty retreat. He had been “incredibly gracious and engaged on the way in,” Marcus Brauchli, the Post’s executive editor, would later say, but after his drubbing Trump had departed the dinner “with maximum efficiency.”
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To all outward appearances, Trump had just been brutally dispatched—his dignity snatched away from him, his foray into politics swiftly cut short, the preening, grasping interloper who had barged into a world where he didn’t belong sent crawling back to his rightful station: a tawdry world of bimbos, pink marble, reality TV, and “Page Six.” This is what all of Washington understood to have happened, for years afterward: Trump had made another of his absurd periodic displays of pretending to contemplate a run for president, ventured too far in his quest for publicity, and suffered a terminal humiliation. Now the universe had snapped back into balance and ejected him.
Only that wasn’t what had happened at all.
Trump had indeed toyed many times before with running. The first time, in 1987, he was about to publish his book The Art of the Deal when a Republican activist in New Hampshire launched a presidential draft campaign. One day that fall, Trump, then forty-one, disembarked from a black helicopter onto an airfield in Hampton, New Hampshire, and gave a speech to five hundred people at the local Rotary Club, many of them waving “Trump in ’88” and “Trump for President” signs. Striking notes that could have been sounded in his 2016 campaign, Trump claimed that the United States faced “disaster” because it was “being kicked around” by the likes of Japan, Iran, and Saudi Arabia, countries that were “laughing at us.” He added, “It makes me sick.” Trump never entered the race. But people responded. He drew headlines. His book became a bestseller.
In 1999, he went a step further, quitting the Republican Party and actively campaigning for the Reform Party nomination. Ross Perot had founded the Reform Party to fight the North American Free Trade Agreement (NAFTA) and push a balanced budget, mounting a pair of White House bids in 1992 and 1996. While the Reform Party has faded from memory, in 1999 it represented a serious political vehicle because it assured its nominee access to all fifty-one ballots and money from the Federal Election Commission. Those said to consider pursuing its nomination included everyone from Oprah Winfrey and Cybill Shepherd to Warren Beatty and Pat Buchanan. Trump, sizing up Winfrey as the biggest star, declared her his dream running mate. While he reveled in the attention that came with his presidential flirtation, Trump also seemed to absorb some of the ideas and tactics that had animated Perot’s success. He rushed into print another book, The America We Deserve, that railed against NAFTA and aped Perot’s famous warning about “a giant sucking sound” of American jobs heading south to Mexico. Perot was a kind of ur-Trump. In an era before Twitter, he used unconventional methods to organize his followers and draw attention to his campaigns, including an 800 number and frequent appearances on Larry King’s CNN show. Although Trump, with characteristic braggadocio, vowed to spend $100 million, he took a page from Perot and relied mostly on a blitz of free media to win Reform Party primaries in Michigan and California, before eventually dropping out (during a Today show appearance).
Trump briefly toyed with challenging George W. Bush in 2004, this time sensing that his opportunity lay on the left. “You’d be shocked,” he told CNN’s Wolf Blitzer, “if I said that in many cases I probably identify more as a Democrat.” As public sentiment soured on Bush after his reelection, Trump stepped up his criticism, hinting to the New York Post that he might run in 2008, although he never took steps beyond orchestrating suggestive leaks to newspapers.
Each of these episodes coincided so obviously with some other angle Trump was pursuing at the time—either hawking a book or promoting The Apprentice, which began airing on NBC in 2004—that people in politics grew inured to them, rolling their eyes as each new self-promotional campaign got underway. So nobody paid much attention when, after Obama’s election, Trump became more active in politics.
In February 2011, he was a late addition to the roster of speakers at the Conservative Political Action Conference, his first ever appearance at the annual cattle call for Republican presidential hopefuls held every year in Washington, D.C. To fan interest in this latest feint at the White House, one of his lawyers had created a website, ShouldTrumpRun.com. “While I’m not at this time a candidate for the presidency,” Trump announced grandly at CPAC, “I will decide by June whether or not I will become one.” Reporters soon realized that his announcement timeline just happened to coincide with sweeps week and dismissed it as a ratings stunt, the usual Trump-presidential-hype cycle cranking up again.
That’s why it didn’t register as particularly significant when Trump, in the same speech, deployed a curious line of attack against Obama, one previously confined mostly to the fever swamps of far-right websites. “Our current president came out of nowhere. Came out of nowhere,” Trump said, shaking his head. “In fact, I’ll go a step further: the people that went to school with him, they never saw him; they don’t know who he is. It’s crazy!”
In the weeks that followed, Trump traveled the talk-show circuit making explicit what he’d merely hinted at in his CPAC speech: his contention that Obama hadn’t been born in the United States, had somehow forged his birth certificate, and therefore was an illegitimate president. “I want him to show his birth certificate,” Trump said, in March, on ABC’s The View. “There’s something on that birth certificate that he doesn’t like.” A week later on Fox News he went further: “People have birth certificates. He doesn’t have a birth certificate. He may have one, but there’s something on that—maybe religion, maybe it says he is a Muslim. I don’t know. Maybe he doesn’t want that. Or he may not have one. But I will tell you this: if he wasn’t born in this country, it’s one of the great scams of all time.”
Trump was plumbing the depths of latent racist hostility toward the president and discovering that there was a lot of it there. Everybody in politics knew this sentiment existed, but the long-standing consensus had been that it should be kept out of the public arena. In the 2008 presidential campaign, John McCain had quickly upbraided a woman at his rally who prefaced a question to him about Obama by stating, “He’s an Arab.” The crowd booed McCain for correcting her.
Trump, who has an uncanny ability to read an audience, intuited in the spring of 2011 that the birther calumny could help him forge a powerful connection with party activists. He also figured out that the norms forbidding such behavior were not inviolable rules that carried a harsh penalty but rather sentiments of a nobler, bygone era, gossamer-thin and needlessly adhered to by politicians who lacked his willingness to defy them. He could violate them with impunity and pay no price for it—in fact, he discovered, Republican voters thrilled to his provocations and rewarded him. National polls taken in mid-April, two weeks before the White House Correspondents’ Dinner, showed Trump leading the field of 2012 GOP presidential candidates.
Privately, what amused him the most, he later told a friend, was that no party official in a position of power dared to stand up to him. In his first nationally televised interview, on C-SPAN, the new chairman of the Republican National Committee, Reince Priebus, was confronted about Trump’s possible candidacy and his birther attacks on Obama. “Is the birther debate good for the party?” Jeff Zeleny, a reporter for The New York Times, asked him. “I think all these guys are credible,” Priebus replied, looking slightly nauseated. “I mean, I think it’s up to the primary voters to decide that. I mean, obviously, people are going to have different opinions. And, you know, you’re going to have a lot of different candidates that are running, they’re gonna talk about different things at different times. . . . I think having a diversity of opinion is fine.”
The lesson Trump took away was that the party gatekeepers, who were privately appalled at his behavior and did not want him in the race, would pose no threat to him at all if he decided to run.
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Obama’s humiliation of Trump at the Correspondents’ Dinner appeared to smother the hype that had been building around Trump for months. Years later, when Trump won the Republican nomination, analysts seeking to understand his rise and how they had missed it would look back at the evening as the catalyst that launched his subsequent climb to the pinnacle of American politics. Essentially, they understood Trump’s pursuit of the presidency to be a revenge fantasy exacted upon his tormentors to establish, with sweeping certainty, his dominance over all who had mocked him.
Trump himself has rejected this view (in no small part, one suspects, because accepting it would involve an un-Trumpian admission that he had indeed been humiliated). “It’s such a false narrative,” he complained in 2016. He added, less convincingly, “I had a phenomenal time. I had a great evening.” Trump also could have pointed out that he had long ago developed many of the themes that became hallmarks of his eventual campaign—everything from the evils of Chinese currency manipulation to the economic damage that NAFTA inflicted on a broad swath of U.S. workers.
What is clear in hindsight, however, is that Trump’s interest in politics intensified right after the dinner, instead of quickly melting away, as it had after each of his presidential flirtations in the past. “I realized,” he said, “that unless I actually ran, I wouldn’t be taken seriously.” For years, Trump had sought political advice from Roger Stone, a junior Richard Nixon henchman turned lobbyist and a notorious self-promoter, whose carefully cultivated image as a master of the political dark arts often seduced wealthy naïfs like Trump (The New Republic once dubbed Stone a “state-of-the-art Washington sleaze ball” for his ability to fleece credulous newcomers). Now Trump decided to broaden his circle of advisers. He turned to Bossie to school him in the rudiments of preparing for a presidential campaign.
Trump’s decision to reach out to Bossie was consequential in ways that he probably couldn’t appreciate because it immediately plunged him deep into the anti-Clinton milieu in which Bossie was a chieftain. The match might have been more or less inevitable. Trump also sought meetings with more mainstream Republican consultants, some of whom had experience in presidential campaigns. But none took him seriously or envisioned any future for him in high-level politics, particularly not after his public comedown from the birther attacks. As he had with Obama and Meyers, Trump registered with them mainly as a punch line.
The connection to Bossie, however, brought entrée to a whole menagerie of characters who were eager to advise Trump and would figure prominently in his future. Most of them belonged to a distinct subcategory within Republican politics: professional anti-Clinton operatives. As Bossie’s own résumé testified, Bill and Hillary Clinton had been prominent Democratic fixtures on the national political scene for so long—two decades, at this point—that it was possible for a conservative to build an entire career out of specializing in devising ways to oppose and attack them. No equivalent job category exists on the left. A liberal simply couldn’t sustain himself professionally by developing a specialized capacity for attacking, say, Romneys or Bushes. Either there wasn’t sufficient continuity across election cycles or, as in the case of the dynastic Bushes, they didn’t inspire the kind of visceral loathing among the opposition that is necessary to maintain a permanent counter-operation. The Clintons, on the other hand, registered to most conservatives as the primary and ever-present enemy.
Through Bossie, Trump forged a connection with people such as Kellyanne Conway, who first rose to cable news fame in the late nineties as part of a trio of blond conservative “pundettes” (along with Ann Coulter and Laura Ingraham) who became anti–Bill Clinton fixtures during the Monica Lewinsky scandal and Clinton’s subsequent impeachment.* Conway’s husband, George T. Conway III, helped to impeach Clinton by drafting the Supreme Court brief when Paula Jones sued the president. The court agreed with Conway’s argument that a sitting president could be subjected to a civil lawsuit. (Clinton’s denial under oath that he’d had sexual relations with Lewinsky eventually led to his impeachment.) George Conway earned a special place in conservative lore by reportedly e-mailing Matt Drudge an infamous tip, which Drudge quickly published, about the shape of the president’s penis. Even Roger Stone, sensing opportunity, had begun fashioning himself into an author of heated anti-Clinton polemical books.
All of these influences helped shape Trump’s view of politics and steer it in a sharply anti-Clinton direction just as Trump was starting to think seriously about running for president. In 2012, he surprised Mitt Romney’s campaign by repeatedly and forcefully offering his endorsement. Somewhat reluctantly, Romney’s team agreed to accept it at a Trump hotel in Las Vegas two days before Nevada’s GOP caucus, though not before taking steps to minimize the association by hanging blue curtains around the ballroom where the endorsement would take place, so that Romney wouldn’t appear to be standing “in a burlesque house or one of Saddam’s palaces,” a Romney aide, Ryan Williams, later recalled. (They missed the gold-emblazoned “Trump” lectern at which both men spoke.) Another adviser was surprised by Trump’s expectation that the campaign would want him to barnstorm the country on Romney’s plane. “We finally had to tell him: it’s not gonna happen,” the adviser said. “He couldn’t believe that we were saying no.” Trump seemed to imagine a role for himself that would have amounted to a kind of dry run for his own campaign four years later.
No one whom Bossie brought into Trump’s orbit would exert a greater influence than Bannon would. Not long after the fateful Correspondents’ Dinner, Bossie, who knew Bannon from fringe conservative circles, brought him along on a trip to Trump Tower to offer advice about how Trump might prepare for a run. By all accounts, the two men clicked right away. Like Trump, Bannon had cycled through multiple marriages and was rich, brash, charismatic, volcanic, opinionated, and never ruffled by doubt. He, too, was a businessman and a deal maker, and he had faced down moguls ranging from Ted Turner to Michael Ovitz. Fluent in the argot of Wall Street and Hollywood, Bannon specialized in media, having moved from financing television shows and films to making movies himself. He had plenty of experience maneuvering among the outsize egos of aggressive billionaires such as Trump and seemed to possess a sixth sense about how to connect with them.
Perhaps owing to this background, Trump, whose habit was to surround himself with obsequious lackeys, took Bannon’s counsel more seriously than he did that of other advisers. “[Steve] was the only alpha male in his universe,” said a Trump associate. When Trump began visiting conservative conferences, such as the South Carolina Freedom Summit, which Bossie hosts each year, he would make a point of seeking out Bannon. “I remember Trump at the Freedom Summit going, ‘Where’s my Steve? Where’s my Steve?’” said Sam Nunberg, an ex–Trump aide. “He loved the guy.” It was clear the connection was genuine, said Roger Stone, “because Steve is a slob, and Trump hates slobs.”
Initially, Bannon was no more inclined to take Trump’s presidential ambitions seriously than anyone else who wasn’t on Trump’s payroll. He also met with more plausible candidates, such as Ted Cruz, Rand Paul, and Ben Carson. Always on the lookout for a new adventure, Bannon viewed the meetings with Trump as a lark and a chance to possibly conscript him into one of his many enterprises.
To prepare for one meeting, Bossie conducted some cursory opposition research, mostly combing through public records, in order to give Trump a sense of where he might be vulnerable to attack. Bannon and Bossie traveled up to New York City to present what they’d found. Trump was astonished when the pair informed him that he had bothered to vote only sporadically and had given money to Democratic politicians. “How did you get that information?” he asked them, unaware that it was readily available in public records.
According to a former Trump adviser, Bannon was also behind a needling stunt Trump pulled two weeks before the 2012 election. Having badgered Obama into releasing his birth certificate the year before, Trump had started insinuating that his passport and college transcripts may also be forged or missing. “I’m very honored to have gotten him to release his long-form birth certificate—or whatever it may be,” Trump said in a blurry video he posted to YouTube. “I have a deal for the president, a deal that I don’t believe he can refuse, and I hope he doesn’t. If Barack Obama opens up and gives his college records and applications, and if he gives his passport applications and records, I will give, to a charity of his choice . . . a check, immediately, for $5 million.” Bannon told an associate he had lined up a donor willing to supply half the sum.
The media, chastened by the birther episode, didn’t bite on this one. But by now, Trump and Bannon had forged a connection, and Trump’s thoughts were already shifting to 2016. “I knew Trump was running in 2013,” said Nunberg, an aide to Trump at the time. “I knew because he got a taste of it in 2012—he was surprised that he was number one [in the polls].” Nunberg called Bannon to make sure he knew they weren’t screwing around. “I remember telling Steve, ‘We’re going to rage against the machine,’” said Nunberg. “And Steve just loved it. I still remember his reply. He goes, ‘That’s amazing, brother.’”
Although neither of them could have had any inkling of where they would end up, Bannon would provide Trump with two great services in the years ahead—services without which Trump probably wouldn’t be president. First, he supplied Trump with a fully formed, internally coherent worldview that accommodated Trump’s own feelings about trade and foreign threats, what Trump eventually dubbed “America first” nationalism. One aspect in particular that preoccupied Bannon—the menace of illegal immigration—was something Trump would use to galvanize his supporters from the moment he descended the Trump Tower escalator on June 16, 2015, to declare his candidacy. By then, Bannon had left banking and Hollywood to take over the combative right-wing populist website Breitbart News after the death of its founder, Andrew Breitbart, in 2012. Breitbart’s fixation on race, crime, immigration, radical Islam, and the excesses of political correctness—as well as the site’s dark and inflammatory style—did much to shape Trump’s populist inclinations and inform his political vocabulary. (An analysis of his Twitter feed conducted after the election showed that Breitbart is far and away Trump’s primary source of news.)
The second service Bannon provided Trump was to conceive and create over several years an infrastructure of conservative organizations that together would work, sometimes in tandem with mainstream media outlets, to stop the woman everyone believed would become the 2016 Democratic nominee: Hillary Clinton. What Bannon built was in essence the very thing Clinton herself was mocked for invoking in 1998: a “vast right-wing conspiracy” designed to tear her down. Bannon didn’t set out to do this specifically for Trump. Rather, Trump was the fortunate beneficiary of an elaborate plot to discredit his opponent—and then, either through luck or foresight, he put the architect of that plot in charge of his campaign for the critical final stretch before the election, producing a result that shocked the world.
How did this happen? Why did no one see it coming? And why did conservatives succeed in stopping a Clinton this time, when they had failed so badly to stop one before?
Many of the answers trace back to the Oz figure of Bannon. Though he befriended Bossie and other veterans of the anti-Clinton movement, he was not a part of their world when Bill Clinton was president. Watching from afar, he developed a perceptive critique of why they failed. “In the 1990s,” he explained, “conservative media couldn’t take down Clinton because most of what they produced was punditry and opinion, and they always oversold the conclusion: ‘It’s clearly impeachable!’” Stunts like Dan Burton’s watermelon murder theory and Bossie’s doctored tapes cost conservatives the public’s trust—and they didn’t even recognize it, until voters took their power away. Bannon’s diagnosis of their chief flaw was simple and direct: “They wound up talking to themselves in an echo chamber.”
To be effective, he believed, a conservative effort to thwart Clinton would need to be based on facts, not punditry, and reach beyond the conservative bubble to turn liberals and independents against her. The insular world of anti-Clinton conspiracists was ill equipped to mount such a campaign, of this Bannon had no doubt. So instead, he drew upon the lessons of his own strange and peripatetic career, which had equipped him with a set of skills and a grand theory about how he could pull it off.