Barack Obama was looking at his legacy. It was march 25, 2019. The former president surveyed the newly elected Democratic members of Congress, face to face with the fractured, shaky future of the party he once led.
The congressional freshmen crowded in front of him were deeply divided, feuding, and facing a dangerous enemy in the White House. The group was looking to Obama for answers.
It was spring in Washington and the bright cherry blossoms that dotted the nation’s capital were in peak bloom. Obama met with the new class at a home of the Democratic Party’s old guard. The reception was held at the mansion of Esther Coopersmith, a doyenne of DC society for over seven decades.
Coopersmith’s stately redbrick mansion was located on S Street, nestled between the Irish ambassador’s residence and the Laotian embassy. Billionaire Jeff Bezos maintained a residence just up the block. This was Kalorama, the elegant neighborhood at the heart of Washington’s diplomatic community, a key node in its influence ecosystem. Unlike the many consulates, permanent missions, and organizations that dotted the leafy streets, Coopersmith’s home never held an official role. Nevertheless, she had turned it into a regular gathering place for the city’s most powerful and a museum of her own significance.
Coopersmith had met every modern US president since Harry S. Truman—all, that is, except the one who then held office, Trump. Signed photographs hung alongside the sumptuous oil paintings, antique vases sat atop marble mantels and mahogany tabletops. Her home had all the traditional trappings of power.
Though Coopersmith was a stalwart of the Democratic establishment, she had a bipartisan and international sense of hospitality. Over the years, her soirees have been attended by presidents, White House officials, a slew of foreign dignitaries, members of Congress, and even the infamous South Carolina segregationist Strom Thurmond. Coopersmith met everyone who was anyone in Washington, had probably invited them to her home more than once for an elegant luncheon or a relaxed dinner, and she had pictures to prove it hanging on the wall—alongside tickets for every presidential inauguration since 1961.
Coopersmith, then in her eighties, had reportedly broken into politics as a young woman in 1952 when she managed the ill-fated presidential campaign of liberal senator Estes Kefauver in Wisconsin. Two years later, Coopersmith came to Capitol Hill for a staff job. She married a wealthy lawyer and built a reputation as a Democratic fundraiser. Coopersmith went on to spend several years as a diplomat and ambassador under Presidents Carter, Reagan, and Clinton. She also earned a reputation as a hostess nonpareil. A New York Times profile from 1987 described Coopersmith as “one of the best at playing the Washington ‘networking’ game” and noted she “concedes that the real impetus for her party-giving is that she enjoys having power at her dinner table.” She was a major donor who paid for the privilege of mixing with politicians. The late senator William Proxmire, a Wisconsin Democrat, described her to the paper as “the Democratic political den mother of all fundraising.”
“She really is, truly, a human catalyst,” former Democratic House Speaker Nancy Pelosi once said at a birthday celebration for Coopersmith. “She just brings people together.”
On this night, it was easy to see what Pelosi meant. The House freshmen stepped out of their cars in the mansion’s trim forecourt, ascended the two white marble steps, strode between the tall cast-iron lampposts into Coopersmith’s twenty-eight-room home, and crammed themselves into the living room with its lemon-colored walls, gold-framed mirrors, and candelabras. The centerpiece of the event wasn’t Coopersmith or her lavish knickknacks, or even Pelosi, who had helped plan the evening. They were there to hear from Obama, the party’s last great champion.
Near the beginning of his remarks, which we obtained in detail, Obama assured the new House members he knew what they were up against. He also acknowledged that Democrats were split on how to confront the urgent threats posed by President Donald Trump and his increasingly militant MAGA movement.
“I know that there are debates right now taking place among the presidential candidates and among the congressional candidates and all of us who care about this country about how do we confront some pretty bad stuff,” Obama said. “How do we confront a resurgence of racist or misogynist attitudes? How do we confront things that we thought were no longer acceptable but have been made acceptable again?”
It was only natural the party would turn to Obama for guidance. He was one of its most politically skilled and popular leaders. Obama’s rise to the presidency captivated the country and, after winning two terms, he left the White House with the approval of nearly nine out of ten Democrats.
As he addressed the intimate gathering in 2019, Obama admitted it had become a “different moment.”
“The Republican Party is different,” Obama said. “I don’t want people to feel as if we have to harken back to what we did then in order to succeed now.”
Obama’s conversation with the freshmen came on a particularly rough day for the party faithful.
Shortly before Obama left office, the US intelligence community released a report showing Moscow had pushed propaganda designed to help Trump defeat Hillary Clinton. The Kremlin campaign included the email hack that inflamed the division between Democrats. In the two years since Obama’s exit, distraught liberals had put their faith in Special Counsel Robert Mueller’s investigation into Russian intervention in the 2016 election, holding out hope he would bring Trump down.
Mueller had delivered his final report to the Justice Department at the end of the previous week, and on the day before the dinner at Coopersmith’s house, Attorney General William Barr released a brief letter summarizing it. Mueller’s probe had already produced sweeping indictments of Russian officials and multiple convictions of key Trump allies. It had uncovered contacts between Trump’s team and individuals linked to Russia. And it had documented myriad ways that Trump had tried to squash the investigation. However, Mueller had not found evidence that the Trump campaign conspired with the Russian government. Barr’s letter—which was later revealed to be somewhat misleading—made clear that the Justice Department would not pursue charges against Trump.
Like many Democrats, Obama and his team viewed Trump as a uniquely insidious foe, not merely a political adversary but someone who might bring the whole American experiment to ruin. As Trump heedlessly broke norms in the White House, they considered what traditions they would be willing to set aside to rein him in. But even in this fevered climate, Obama made clear he hadn’t lost his appetite for diplomacy.
“What I do believe is that the principle of reaching out beyond the people who completely agree with you is a good principle to follow,” Obama said. “You know, as I tell sometimes when I talk to young people, if you don’t talk to folks who aren’t woke, they’ll never wake up. You’ve got to be able to have some conversation with folks who don’t align with you on every issue.”
At this point, in March 2019, Obama had only recently come out of the political hibernation he had imposed on himself upon leaving office two years earlier. While Obama had largely left the public eye, he had stayed in Washington so that his daughters could finish school. Obama had once looked forward to a president’s traditional retirement, working on the task of writing his memoirs, and letting the next president do his—or, preferably, her—job. But then Donald Trump had beaten Clinton and it complicated his plans.
Obama initially resisted the entreaties to help his fellow Democrats fight Trump. He had made all his arguments during the 2016 campaign, doing his best to summon the better angels of Americans’ nature against Trump’s demagoguery.
“He’s betting that if he scares enough people, he might score just enough votes to win this election. And that’s another bet that Donald Trump will lose,” Obama had thundered during the Democrats’ convention in Philadelphia. “And the reason he’ll lose it is because he’s selling the American people short. We’re not a fragile people. We’re not a frightful people.”
But it was Obama who had bet wrong.
Obama’s first public speech after leaving office, in April 2017, didn’t once mention Trump’s name. He largely avoided the midterm primaries. However, by the final months of the 2018 race, the former president had made appearances in multiple states and earned a reputation as a “closer” who could help secure victories for the Democrats.
Standing at a lectern in late October, Obama didn’t need to stake out a place on the spectrum between Clinton’s moderate establishment politics and Sanders’s transformative reimagining of the American system. Obama could simply root for the Democrat on the general election ballot, and tout voting as the remedy for an ailing democracy.
Coupled with deep anxiety and dissatisfaction with Trump’s daily parade of scandals, the late campaign appearances from Obama and his wife, Michelle (who may have been even more popular than he was at that point), helped the Democrats summon what was widely dubbed a “blue wave” that swept them into the majority in the House of Representatives.
At the Coopersmith residence in Kalorama, Obama met the new Democrats he had helped bring to power and faced their questions. His answers provided a unique glimpse into his closely guarded thinking on many of the party’s core issues.
“I think that this was the most candid I had ever seen Obama, because it was a safe space,” California’s Katie Hill, who had handily won a race in a competitive district in Los Angeles’s northern suburbs, said in an interview for this book.
Obama relished playing the party elder and cheerleader-in-chief. In front of the room alongside Pelosi, who had helped arrange the gathering and served as the master of ceremonies, he began the formal discussion of the evening by gushing to the new members, “I’m so proud of all of you.”
“I think you are going to be outstanding. Not just for the remainder of this Congress, but for a long time to come,” Obama said.
“And you have a really good example in the Speaker of the House,” he continued. “Most of you know I love Nancy Pelosi. I mean [her husband] Paul knows it. Michelle knows it. I mean, I just love Nancy—I don’t lie about it.”
“I love you too,” Pelosi shot back immediately.
The warm banter between the two of them sent a wave of laughter rolling through the crowd.
“Many of us had met President Obama before at various campaign events and other fundraisers or whatever, but this was definitely the most intimate setting, in somebody’s living room,” said Hill.
The night was Pelosi’s as much as Obama’s. At that time, the senior and most powerful elected Democrat in the nation, she had been in Congress since 1987—longer than some of the new members at the event had been alive. Pelosi had been Speaker once before during a stretch spanning the end of George W. Bush’s presidency and Obama’s first two years in office. It was a moment when the party had ridden the coattails of Obama’s unique brand of celebrity to huge majorities in both houses of Congress. With that supermajority, Pelosi had wrestled the Affordable Care Act, Obama’s signature health care bill, across the line.
“There is not a piece of legislation that I passed or an initiative that I was able to accomplish during the course of my presidency that [didn’t] happen, in part, because of the extraordinary leadership that Nancy already showed,” Obama said.
After losing the Speaker’s gavel in the Tea Party–driven midterms rout Democrats suffered in 2010, Pelosi hung on as party leader for eight years in the minority. She gained the gavel back again thanks to this new group of Democrats, and she kicked the conversation off by celebrating the fact they had made it the most diverse Congress in history.
“Before we were fifty percent women, people of color, LGBTQ,” Pelosi said. “With the arrival of this class we are now sixty percent women, people of color, LGBTQ.”
Pelosi had been there long before Obama, and she was still in power years after he left office. To some Democrats, she was the lioness who had saved Obamacare. For others, she had failed to do enough with that rare supermajority. The left viewed her as a prime example of how the party’s aging leadership was blocking a younger generation from setting ambitious new priorities.
Obama’s choice to speak to the freshmen rather than the broader Democratic caucus meant he wouldn’t encounter any of the presidential candidates who were already hatching campaigns in the halls of Congress that spring. A little over a month before the gathering at Coopersmith’s home, Bernie Sanders had officially announced another White House bid to “complete” the “political revolution” he had started in 2016. He would ultimately be joined in the field by five other sitting senators as well as four House members who hoped to lead the party against Trump.
By 2019, the question of an endorsement already hung over Obama. Besides the many Democrats in Congress with dreams of the White House, Obama had to consider his loyal vice president over two terms, Joseph Robinette Biden Jr. About a week before Obama’s reception with the new members, Biden had telegraphed his own desire to run with a slip of the tongue where he dubbed himself one of the candidates who was “running” before correcting and reframing it as a hypothetical.
As the discussion began, Obama noted he and Coopersmith were neighbors. Kalorama was supposed to be the site of his quiet retirement. Obama and his wife had purchased an $8.1 million mansion of their own shortly after signing a publishing deal that was reportedly worth over eight times that amount.
“This is a little more intimate group and my goal is not for us to have … speeches and sound bites but to actually have a conversation. And since this is really close to my house, we can hang out for a while,” Obama quipped.
After the jokes and pleasantries, the questions began. Pelosi selected new members to stand and address the former president. They had only been sworn in about two months before, but the freshmen had already begun sorting themselves into the factions that made up the Democratic delegation.
There was the Congressional Progressive Caucus, or CPC, a large and heterogeneous collection of about one hundred left-leaning members. Others joined the New Democratic Coalition or New Dems, a similarly sized group of avowed centrists. Beyond those major ideological groups, there were racial and multiethnic organizations like the Congressional Black Caucus and the Congressional Hispanic Caucus, as well as smaller organizations like the Blue Dogs, a handful of the most conservative Democrats, and the Problem Solvers Caucus, a bipartisan group ostensibly focused on compromise.
It was the Capitol Hill equivalent of a high school lunchroom. As they joined the various groups, members needed to account for the poll numbers and preferences of the voters as much as their own personal preferences. Some were part of multiple coalitions, but there were also bitter rivalries. A member might, for example, join both the Blue Dogs and the New Dems. However, it would be hard to imagine a Blue Dog being part of the CPC.
Four of the freshmen had formed their own small group, which they called “the Squad.” They were supported by an organization called Justice Democrats, which was founded by Sanders campaign alumni and dedicated to his mission of pulling the party leftward. Two of them—Alexandria Ocasio-Cortez and Ayanna Pressley—had won their seats after defeating powerful establishment incumbents. In the months since their primaries, the quartet had sparred noisily with party leaders while generating a maelstrom of media attention. Pelosi had a particularly fraught relationship with the group. While they were not necessarily following her lead, perhaps they might listen to Obama.
The first questions for the former president came from the center. Michigan’s Haley Stevens and Texas’s Colin Allred, a pair of New Dems who were presidents of the freshman class and had both served in Obama’s administration, stepped up and asked how the party could maintain a “positive” message while taking on Trump. It was a fraught, fundamental question that indicated just how much Democrats were struggling to find their footing.
Obama admitted that it was a “different era” from his time in office and encouraged the pair to reach out to people with different views.
But, Obama said: “You don’t have to sing ‘Kumbaya’ and pretend to paper over differences. You don’t have to chase a phony bipartisanship that somehow—if we just split the difference between sane and crazy—that somehow, we’re better off.”
Nor did Obama think Democrats should adopt Trump’s smashmouth rules.
“This idea that somehow, we can give as good as we get, I think, is a losing proposition. Because when we get that nasty and dishonest and make up stuff … unmoored from facts, that’s playing in their field,” Obama said.
Obama had direct experience with the sitting president’s malice. Trump’s transition from Page Six to presidential politics owed a great deal to his promotion of the racist and thoroughly debunked “birther” conspiracy theory, which held that Obama was actually born in Africa and, as a result, disqualified from the White House. The Republican Party’s media ecosystem had stoked its audience’s rage with racial and cultural resentment during Obama’s time in office. Trump was the distilled expression of that anger.
Obama implied that race was at least part of why he, as a Black man, would not be able to practice Trump’s angry and factually challenged brand of governance.
“Like I couldn’t do what the guy in office currently does.… It’s not just an issue that I couldn’t get away with it, it’s that—that’s not who I am,” explained Obama. “Don’t fall into the trap of thinking that being tough involves being mean. Don’t fall into the trap of thinking that being effective means that you have to set aside some core values that help get you here.”
Then, Hill spoke. Fresh off an approximately nine-point victory against a Republican incumbent, she, like many of those in the room who needed independent and moderate voters to win, was worried about young people who demanded Democrats take a more aggressive, progressive approach.
“We’ve seen a gap of young people voting for Democrats by thirty-five points and we’ve seen historic turnout among young people in this past election,” Hill began, adding: “But also, there are many of us who flipped districts in these more conservative seats, so when you’re talking about progressive policies … that mobilize and inspire young people, they don’t always align with those that might be the ones … you’re most inclined to support if you’re in a red to blue seat. So, I am just wondering if you had any thoughts on kind of balancing that.”
Hill, who had been seen as a rising star by the party’s establishment, would later become a vivid example of how some members of the party were seeking to hold their behavior to the higher standard Obama was advocating.
The issue wasn’t limited to Trump’s coarse language and many ethical lapses. At the time, society was in the midst of a broader reckoning. The MeToo movement that began with high-profile sexual assault and harassment cases in Hollywood was spreading to misconduct in government as well. During the Trump era, Democrats sought to cast themselves as the party that respects and believes women and lives by a higher standard of behavior. However, they also found taking the high road came with a political toll. In late 2017, Minnesota senator Al Franken, a popular figure among the Democratic base, stepped down after he faced accusations from multiple women. Franken’s case played out abruptly and he would later say he wished that he had stuck around to see through an investigation of the claims against him, some of which were called into question by subsequent reporting. That feeling was shared by some Democratic politicians and wistful supporters.
Seven months after the night in Kalorama, Katie Hill herself would resign amid allegations she had inappropriate relationships with multiple staffers. Her choice to leave amid controversy rather than holding on to her seat and fighting off the scandal was driven in part by a desire to maintain the image of a Democratic Party that had more stringent ethical standards than their opponents.
“I didn’t wanna give any other fodder to the motherfuckers on the other side,” Hill said of her decision to resign.
Hill’s story showed the price Democrats could pay for pursuing Obama’s high-minded politics. Following her exit, the district flipped back to the Republicans.
In Ms. Coopersmith’s ballroom, Obama responded to Hill’s question by urging the freshmen to focus on hands-on leadership, and providing direct services. He related that the number-one suggestion of his first Senate chief of staff, the veteran Capitol Hill hand Pete Rouse, was to answer the mail from constituents.
“Somebody sent you here to do a job and you have to respond to them,” Obama said. “You work for them. You don’t work for CNN. You don’t work for Twitter. You work for them. And that, I think, is a useful thing to remember.”
Obama heard in Hill’s question a genuine anxiety about how freshmen in purple districts might hold their seats. He warned them against being overly preoccupied with their poll numbers.
“Don’t operate out of fear. One of [the] things that I was surprised about when I got here is, I’d met people who fought really hard to get into the Senate and they were afraid of their own shadow,” he said, recalling senators he’d seen who were constantly hedging in light of their reelection prospects. “There has to be a time at which you’re actually going to do something that you care about. And if it’s significant then it means that … there are going to be some people who don’t like it.”
Growing philosophical, Obama advised that, for a politician, “the vanity of holding office should burn away fairly quickly; it’s not lasting, it’s insubstantial” compared to holding onto one’s convictions and delivering for one’s constituents.
In other words, they weren’t in Washington simply to enjoy the perks of political notoriety.
“Remember why you got here and don’t start thinking that the reason you want to stay here is because you got a pin on, and you got an office, you’re on TV once in a while. First of all, nobody watches cable TV … ordinary people aren’t reading Politico. If you want to be famous, go to Hollywood. Do something, you know, be a celebrity for the sake of being a celebrity. But it’s not worth all the sacrifice your family makes; it’s not worth calling donors—” Obama said, allowing a burst of laughter and applause from the young politicians to drown the end of that sentence.
Obama was reminding the members they were elected to perform a public service.
“All that stuff is only worth it if there’s something that, at the end of the day, you feel like, ‘Man, I’m proud of that, I know that helped somebody, I know that made the country better,’ ” he said.
As for the young voters that Hill had fretted about, Obama pointed out they “have a pretty good nose for who’s in it for the right reasons and who’s sincere.” However, even as he urged the freshmen to be heartfelt, Obama admitted they can’t entirely ignore political realities.
“I want to make sure that I’m not having all of you … go in front of the Capitol and set yourself on fire,” Obama said. “You guys are also politicians and … you are obligated to think through how you can be effective. And for me, at least, the way I always used to think about it was that I would never compromise on my core positions, but I think strategically and tactically about ‘How do I advance them?’ and ‘How do I talk about them?’ ”
As an example, Obama pointed to a maneuver from early on in his White House tenure. During his historic “HOPE” campaign in 2008, he had vowed to end the military’s “Don’t Ask, Don’t Tell” policy, a compromise with the right made by President Bill Clinton that banned gay people from serving openly in the armed forces. Obama told the story of how he strategically took a slower path to that promise.
Ending “Don’t Ask, Don’t Tell” was “important” to him, he said, but he also worried it could be controversial. Obama described bringing together members of his cabinet to come up with a plan.
“So, I brought Bob Gates, the then defense secretary, and I told him, I said ‘Look, we’re going to end ‘Don’t Ask, Don’t Tell,’ but I recognize this is a transition that folks have to wrap their heads around, so how are we going to do this?’ ” Obama recalled. “Then I got the Joint Chiefs, and essentially Jeh Johnson who was an extraordinary lawyer and African American who was general counsel over at the Pentagon … came up with the idea of, look, let’s do like a year-long survey of all the troops and find out how are they thinking.”
The survey bought time. It also undermined a core argument from opponents who had argued soldiers would be uncomfortable serving with gay colleagues. The survey results helped give Obama the political capital to end “Don’t Ask, Don’t Tell” two years into his first term. Speaking to the new members, Obama framed the story as an example of how Democrats needed to find a “balance” between progressivism and pragmatism.
“I just want to make sure that you heard the point. The key point is, you have to be principled. That doesn’t mean you have to be absolutist. That doesn’t mean you have to be impatient. That doesn’t mean you have to be sanctimonious with your fellow Democrats,” Obama said.
Lauren Underwood, a progressive who had taken out an established incumbent in the midterms, was up next. Her question returned to one of the more pressing puzzles facing the party: young voters.
Voters under thirty overwhelmingly back Democrats, which should theoretically cement a major advantage for the party. However, older voters are far more likely to show up to the polls. Turnout rates for the younger demographic are typically at least 10 percent lower than they are for those above the mark. There are similar trends among voters of color. Overall, the dynamic has made voter engagement something of a holy grail for Democrats.
Those younger voters who did come out had been showing far more enthusiasm for Sanders and the new wave of progressives. They also had a sharp hunger for social justice and for increased equity for people of different races, religions, national backgrounds, sexualities, and gender identities. Even some proponents of the progressive economic agenda were wary of the identity issues and cultural concerns some younger activists saw as urgent priorities. Embracing the needs of the new generation risked potentially turning off more moderate voters or falling prey to Republicans eager to paint new political correctness and gender equality as a dangerous ideology.
When Underwood asked Obama for his “thoughts about engaging young people,” the former president responded that there is “power in people just being seen and recognized.”
“When we lose them, it’s because they don’t feel seen and they don’t feel heard,” he added.
Obama then harkened back to his roots as a community organizer.
“When I used to organize, one of the basic principles was, before you ask people to do something, no matter what it is, try listening to them first. Try. It’s a magical thing. You take the time to listen to other people. Find out what is on their minds, find out what their issues are but, more importantly, find out what their stories are, right?” Obama said. “Because we have a story inside us that’s sacred about how we see the world and meaning and our deepest values.”
Obama also shared an anecdote from his first presidential race.
“One of the reasons my campaign back in ’08 did well with young people: It wasn’t just that I was young; we just put them in charge. We were all like, okay you figure this out. Go,” Obama said. “So, they come to the office, yeah there [was] grunt work but there was also ‘Oh, we’re just going to drop you off in the middle of a cornfield, and you figure out how all those people are going to end up caucusing for Obama.’ ”
Rather than giving young staffers a “script,” Obama said his campaign encouraged them to “just go talk to people and listen to them and find out what they care about.” He made the case that being “predisposed to the power of those young people” and listening to them was how Democrats should operate on the Hill in between elections, as well as on the trail.
“That’s true in campaigns, I think that’s true as a party. That should be true in your office, by the way,” said Obama.
Obama broke down the math that made young voters such a vital target for Democrats. Most Americans support the party’s platform of reproductive rights, increased access to health care, gun control, and gay rights. It’s just a question of who’s actually motivated to vote.
“You’re not going to get one hundred percent involved. It’s never going to happen. But as all of you, I think, are aware, if you get a ten percent boost in the youth vote in the next election or in your district, then it is basically a different match,” Obama explained. “This is not a fifty-fifty country. This is a sixty-forty country except older folks vote more. And our folks are distracted, discouraged, disempowered, and so we have to work to make them feel included and empowered. But if we do, they’ll respond.”
Obama was one of the few Democrats among his contemporaries who managed to captivate both young voters and older ones. As he talked to the freshmen at the Coopersmith mansion, he showed why he had been so good at bridging the party’s many gaps. Obama could be both the progressive candidate who ran on hope and the enthusiasm of young Americans and the sober, sensible pragmatist who steered a safe course. In the years since his departure, the party had struggled to find a similarly unifying figure.
The next question came from Conor Lamb, who had been elected to Congress in a special election in March 2018. In an interview for this book, Lamb said he was caught “off guard” since Pelosi “cold-called” on him rather than letting him know he would be part of the event. And, like many of the new members in the room, he was somewhat awed by Obama.
“He was someone I really admired, obviously,” Lamb said of Obama, adding, “This is a personal thing, … you know, when I was a Marine officer, he was the commander in chief.… I just always looked up to him.”
Lamb’s rise was held up as proof that a more moderate version of the Democratic Party could deliver swing districts. He won an upset in Western Pennsylvania, a hotly contested swath of a key battleground state filled with shuttered steel mills and white working-class voters who had ditched Democrats to back Trump. Those voters fascinated the political press, as did Lamb. He was cast by pundits as living proof the arguments espoused by Sanders and Ocasio-Cortez, and her progressive Squad, were losers on the national level. Lamb had won his seat by presenting himself as a pro-gun and not-necessarily-pro-abortion independent who was against increasing the minimum wage and opposed Sanders’s vision for a single-payer health care system.
Over the next two years, Lamb would increasingly get drawn into arguments with progressives. A little over a year later, Ocasio-Cortez called him out by name in an interview where she criticized his campaign strategies. Lamb fired back by suggesting her strident progressivism was “damaging” in swing states. By 2021, Lamb was running for Senate against a more progressive opponent, John Fetterman, and telling reporters he would not accept any endorsement from Sanders. Fetterman ultimately won their race.
Yet, as he questioned Obama, Lamb said he was eager to focus on common ground between the warring wings of the party. He asked if Obama could offer advice on how to “focus” on policies like social security.
“You know people in Western Pennsylvania, at least, overwhelmingly asked about the same things over and over again: social security, Medicare, prescription drug prices. It is kind of amazing to come down here and see how many other issues get put on the table day to day,” Lamb said.
Expanding social security was an area where Lamb and the left were in agreement. He and Sanders were co-chairs of a caucus dedicated to the issue. At the moment he brought it up to Obama, Lamb said he was eager to see the policy—and economic concerns more broadly—become a central part of Democrats’ public engagement.
“I felt like our day-to-day legislative focus was not very concrete and economic as far as the things that we were offering,” Lamb recounted later on. “It may have been just because the Trump vortex made it impossible for us to set the agenda. But I think at the time I was hungry to see Democrats set an agenda that was not about Trump and that was more about the people we were representing in their basic economic concern.”
Obama responded by acknowledging the larger debate Lamb had waded into.
“I will say—just a little bit editorializing—because I know there has been this discussion about—in the Democratic party, there’s like super, super progressives versus the moderately progressive. And then there’s the somewhat conservative progressives. Everybody wants progress,” Obama began.
Obama continued by saying social security was an area where Democrats should be willing to make the kind of fundamental changes to the economic system that progressives clamored for.
“I think people feel deeply insecure about the economy right now in all sorts of ways despite the fact that we’ve got a great economy, relatively speaking.… I mean I left a really good economy but … we didn’t fix some of the core structure stuff that is part of making people feel insecure. The wages still don’t go up as fast as profits do. Inequality continues to rise,” said Obama. “And so, I think it’s important for us to protect things like social security that people care about, and they feel is like a lifeline for them. But I think it’s entirely appropriate for us to try and reimagine what some of our social arrangement institutions are and update them for this new economy.”
Even as Obama embraced the left’s concerns about economic inequality, he trotted out the standard centrist rebuttal to the progressive agenda, that they had no way to fund their ambitious ideas. Obama said the voters in places like Lamb’s district don’t “believe in free lunch” and, if you’re proposing to have the government give them something, they “kind of want to know ‘well, how are you going to pay for it?’ ”
Progressives like Sanders and Ocasio-Cortez reject the suggestion they can’t fund their proposals. Raise taxes on the wealthy and cut the defense budget, they argue, and the government will find it has abundant revenue to fund expanded social programs.
But Obama was zeroing in on a core component of those Pennsylvanians’ stories. Those voters, he said, “have a responsibility gene”—one, Obama added, “that apparently doesn’t apply to the folks who create trillion-dollar deficits.”
It was likely a lightly veiled shot at Trump and Republicans in Congress, whose ambitious tax cuts—which were not offset by any reduction in outlays—had swollen the federal deficit by nearly 17 percent in the previous fiscal year, and would top a trillion dollars a year before the next presidential election. Of course, those Republicans would probably point out that Obama ran up some trillion-dollar deficits himself in the early years of his presidency.
Still, Obama deployed the Republican excesses as a cautionary tale for progressives.
“We have to think practically about how we imagine these big ideas, we have to think about how to pay for them,” Obama said, adding, “None of us as Democrats should be afraid of big, bold ideas. But we should also hold ourselves accountable to think of the nitty-gritty of how those big bold ideas are going to work.”
Obama also warned that even staunchly progressive voters might not “automatically sign on” if they were told a given policy would raise their taxes substantially.
The nuanced discourse at Esther Coopersmith’s ballroom was typical of the forty-fourth president, who had joked early on in the reception about his “bad habit of giving too long of answers.” As the one-time candidate of “hope,” his remarks were, at the very least, sympathetic to the concerns of the left and their youthful base.
But a source who worked with the Squad said the group of progressive freshmen viewed the session with Obama as a “chastising.” According to the source, the Squad members who were able to attend were “excited” to see Obama, who won the White House in 2008 as a progressive taking on the establishment. They left the room feeling let down by Obama’s remarks, much as they did with his time in office.
“They felt like parts of it were targeted at the Squad and trying to get them to settle down,” the source said. “It was disappointing.… Candidate Obama was who they were looking for, but second-term Obama showed up.”
Despite his best efforts to stay above the fray, even Obama, the master tactician, was finding himself caught in the party’s divisive new dynamics. DC’s newest Democrats had come to Esther Coopersmith’s mansion that night consumed by questions. Could they beat Trump? What was the path towards winning over young voters without losing purple states? How should they strike a balance between aspirational, transformational politics and cold, hard realities?
On that night in Kalorama, Obama attempted to give them a road map. He had a deep-seated desire to unify the party to unseat his successor, Trump. However, his answers hadn’t sold everyone in the room. Which led to the biggest question of all: If Obama, the party’s most magnetic leader, was not able to articulate a way forward, then who could?
Obama departed into the soft air of the spring evening, returning to his writing desk and his memoirs. The House freshmen filed out to an uncertain future. For now, this was Trump’s Washington, the damage Democrats inflicted on themselves in 2016 remained unhealed, and the leader of hope and change had left the next generation to sort out the party’s future on its own.