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Today, almost every Democratic presidential campaign starts with what one close adviser to Barack Obama calls “The Pilgrimage”: the journey to the West End to meet the former president.
The West End of Washington, D.C., sandwiched between the better-known districts of Georgetown and Dupont Circle, is known as a neighborhood that people travel through, not to. For elite Democrats, that changed four years ago when Obama set up his personal office here. You wouldn’t know from outside that one of its bland concrete and glass building houses the man whom polls rank as the most popular Democrat in America, and who, according to one global survey, is the second-most admired man in the world.
The first presidential pilgrims started in early 2018, and they continued to trickle through this summer. Not every declared candidate has met with Obama—Andrew Yang and Tulsi Gabbad were notable no-shows—but he let it be known he was available to anyone seeking advice. As a rule of thumb, the closer one is to Obama personally, the less important the West End summit is. Joe Biden, one of only two candidates who Obama knows at a familial, rather than strictly professional level, was an “exception,” said an Obama adviser, who had a rolling series of conversations about 2020, the most recent of which was backstage at the funeral for Elijah Cummings in Baltimore on October 25. Deval Patrick, a close Obama pal and board member at the Obama Foundation who parachuted into the race last week, checked in with a phone call before announcing.
For the others—Elizabeth Warren, Bernie Sanders, Pete Buttigieg, Kamala Harris, Cory Booker, Beto O’Rourke, Steve Bullock, and more—the meeting was as important as planning their kickoff rally or first campaign ad. Obama’s lair is more Restoration Hardware than Oval Office: lots of dark wood (his desk and an enormous mirror behind it), bronze accents (the bookcases), and neutral upholstery in a seating area. Obama is discreet with his guests. He knows how a stray comment could leak and change the course of the race.
He has said he usually offers three big points: Don’t run if you don’t think you are the best person to be president; make sure you understand the toll a campaign will take on your family; and ask yourself, “Can you win?” As he put it recently at a donor event in Washington, “Not are you guaranteed a win, but do you have a theory, a pathway whereby you win not just a primary but you also win a general election, because there is not an empty exercise if you, in fact, get in. Your goal should be to actually ultimately become the president and then be able to lead the country and the world in a serious way.”
Ostensibly the meetings are for the aspiring candidates to gain some wisdom from the last Democrat to win an open presidential primary and the presidency, but they also allow Obama to collect his own intelligence about what he and his closest advisers have made clear is all that matters to him: who can beat Donald Trump.
Sometimes he offers candid advice about his visitors’ strengths and weaknesses. With several lesser-known candidates, according to people who have talked to him or been briefed on his meetings, he was blunt about the challenges of breaking out of a large field. His advice is not always heeded. He told Patrick earlier this year that it was likely “too late” for him to secure “money and talent” if he jumped in the race. Occasionally, he can be cutting. With one candidate, he pointed out that during his own 2008 campaign, he had an intimate bond with the electorate, especially in Iowa, that he no longer has. Then he added, “And you know who really doesn’t have it? Joe Biden.”
Publicly, he has been clear that he won’t intervene in the primary for or against a candidate, unless he believed there was some egregious attack. “I can't even imagine with this field how bad it would have to be for him to say something,” said a close adviser. Instead, he sees his role as providing guardrails to keep the process from getting too ugly and to unite the party when the nominee is clear. There is one potential exception: Back when Sanders seemed like more of a threat than he does now, Obama said privately that if Bernie were running away with the nomination, Obama would speak up to stop him. (Asked about that, a spokesperson for Obama pointed out that Obama recently said he would support and campaign for whoever the Democratic nominee is.)
The post-presidency of Obama is unlike any other. Many presidents have had to navigate the tricky politics of leaving office when a president from the other party takes over. And plenty of presidents have had to grapple with the delicate situation of their vice president seeking a promotion. But Obama has to grapple with both situations simultaneously, and under unprecedented conditions: Obama is under near daily personal assault from the president, who has tweeted about him relentlessly in the past three years, often accusing him and his top officials of an array of crimes, a situation that no ex-president has faced or even imagined. (In 2001, during the presidential transition, it was considered a scandal when Clinton staffers mischievously removed the W keys from many White House computer keyboards before George W. Bush’s staff arrived.)
For many Democrats, former President Obama can be as maddeningly cerebral and detached as President Obama was. In early 2017, there were desperate cries for him to become more engaged in response to Trump. Obama mostly resisted those calls. But then gradually he started to speak up, and then he started to make endorsements and speeches and give advice, and by the fall of 2018 he was so involved in campaigning for the midterms that he could credibly take some responsibility for winning back the House, the single most important check on Trump’s presidency.
As the presidential race unfolded this year, the cycle looks familiar. Obama disappeared from public view, dispensed his advice privately during his West End sessions, and infuriated close political friends, and not just Biden, who wanted a nudge. But recently he has started to speak out publicly, offering Democrats, in two appearances, a unified Obama theory of how they can win—and how they can stave off the same kind of forces that took over the GOP.
‘It was very intense’
Obama designed his post-presidency in 2016, at a time when he believed Hillary Clinton would win and Biden would be out of politics. With a handpicked successor as president and his former vice president happily retired, Obama planned on focusing on setting up his foundation, writing a memoir and devoting his energies to long-term issues like developing youth leaders around the world. The most overtly political aspect of his original plan was an initiative to fight gerrymandering, now up and running in the form of the National Democratic Redistricting Committee. But even that endeavor, which is led by his close friend and former attorney general, Eric Holder, is relatively nonpartisan: The group advocates for fair legislative maps, not just newly redrawn districts designed to benefit Democrats.
But the original plan of a relaxed post-presidency of writing and thinking and mentoring, one that was relatively unencumbered by partisan politics, was blown up by the twin surprises of Trump’s victory and Biden’s decision to challenge him in 2020. Instead of remaining above the fray, Obama was forced back into the center of politics by Trump and Biden, who, for opposite reasons, talk about him and his legacy at every opportunity.
“In a perfect world, he would have retreated to a greater degree from public life than he has, much in the same way that I think George W. Bush did in his post-presidency,” Holder told me. “He would have liked to have been, though he’s too young, an elder statesman.”
This was not the hand he got to play. Throughout 2017 the main struggle of the small staff Obama assembled in the West End was how to deal with what they viewed as a crazy president personally obsessed with Obama. After running against Obama’s legacy, and then holding one awkward but collegial meeting in the White House—“He knows absolutely nothing,” Obama privately told a visitor about Trump, immediately after the meeting—Trump discarded historical precedent and began attacking Obama personally as he worked to overturn his policies. For the most part, Obama and his staff chose to ignore the personal and weighed in only on big policy questions.
Even after the election, Obama still “held out hope” that he and Trump could have some kind of normal president/former president relationship, similar to how Obama and George W. Bush operated in 2009. “He wanted to be a resource,” said Kevin Lewis, Obama’s first post-presidential press secretary. “What we didn’t expect at the level that it was done were the attacks.”
There was one attempt to connect Trump and Obama for a conversation in 2017, when Trump called to thank him for the note he’d left in the Oval Office, but Obama was already on his way to Palm Springs. They never connected again.
In retrospect, this isn’t just when the two leaders diverged; it’s also when Obama began to diverge from what his own party was hoping, and often pleading, for him to do. Two of Obama’s favorite and most frequently cited quotes from Martin Luther King Jr. describe opposite modes of activism. The first quote—“the fierce urgency of now,” from King’s “I Have a Dream” speech—is about immediate change in the face of a sudden threat. The second one—“the arc of the moral universe is long, but it bends toward justice,” which Obama had embroidered into his Oval Office carpet—counsels patience and working toward incremental change over the long term.
With Trump’s victory, most Democrats were suddenly in a “fierce urgency” mood, while Obama retreated to an “arc of the moral universe” post-presidency. It was Lewis’ job to help Obama figure out the balance. The plan was to stay quiet, let other Democrats step up as the face of the party, and weigh in only when, as Obama said at the time, “our core values may be at stake.” The first test came within 10 days of leaving.
Just as they were getting settled in at the West End office, Lewis recalled, the White House issued its executive order banning immigrants from several countries with majority Muslim populations. Lewis and others huddled to discuss “whether or not we were going to say anything about the Muslim ban.” Obama’s concern was the long-term damage: Would a statement from him permanently break the norm that a president should refrain, at least in the initial months, from attacking his successor, which he believed was a vital part of the peaceful transition of power in America? Obama was on vacation in Palm Springs, and he and his aides debated. “It was very intense,“ Lewis said. “Do we have this come from him? From me?” They settled on a statement from Lewis that said Obama “fundamentally disagrees with the notion of discriminating against individuals because of their faith or religion” and was “heartened” by the activists protesting the ban.
It was the beginning of Trump’s effort to repeatedly drag Obama out of retirement. “He needs an enemy,” said Lewis of the president. A few weeks later, on a Saturday in early March, he was awakened just after 6:30 am to a phone exploding with emails and Twitter notifications. “Trump was tweeting out a false claim that President Obama wiretapped him in Trump Tower,” Lewis recalled. “What do you do?” Obama told Lewis and other aides that they would have to respond or Trump’s lie would be taken seriously. “He desperately wanted to adhere to the precedent but it was an unprecedented moment. So we focused more on addressing the lie than talking about Trump’s character.”
Obama tried to maintain a sense of normalcy. His social media feeds became an unusual mix of book and movie recommendations, appeals to help the victims of natural disasters, and tributes to statesmen or celebrities who passed.
Just figuring out a normal private life in Washington could sometimes be difficult for him and Michelle. “They divide the world into two halves: people who knew them before they were famous and everyone else,” said a former political adviser. “They are very walled off. They are afraid of hangers on.”
When Obama tried to join Woodmont Country Club, a predominantly Jewish club in Rockville, Maryland, some members tried to block him because they deemed his views on Israel to be insufficiently supportive of the Jewish state. When that tiff became public, Obama joined Columbia Country Club, in Chevy Chase, instead (“Mostly white Catholics,” said a member there). It wasn’t the end of his golf club difficulties. Columbia has a strict policy that allows members to have just one guest at a time, but Obama was bringing three. “There was a whole internal process to figure out how to tell him,” the member said. “He just seemed to not know. And once he was told he was compliant.”
‘There was a time where I might have been a Republican’
As Trump’s first year plowed onward, Obama’s public statements inevitably became, longer, more frequent, and signed by Obama himself, not his spokesman. The first, in the spring, well before Obama had wanted to speak up, it was Trump pulling out of the Iran nuclear agreement (“misguided“). In the summer, as a Senate vote to repeal the Affordable Care Act loomed, he wrote a long missive to Republicans making the case for preserving it. (After Sen. John McCain cast the deciding vote killing repeal, Obama called and thanked him.) In the fall, he spoke up when Trump rescinded the Deferred Action for Childhood Arrivals immigration program (“wrong,” “self-defeating,” “cruel”).
Obama has the most followed Twitter account in the world, but rather than use it as a political weapon, he acts more like a celebrity social media influencer. He’s also a social media skeptic. One of his recent book recommendations was The Shallows, Nicholas Carr’s examination of how the internet is turning our brains to mush. While many of his closest advisers are well-known Twitter combatants, Obama has consistently voiced skepticism about the partisan “siloing” that social media encourages.
Obama’s public initiatives still hew to his original strategy to serve as a removed ex-president, engaged but above the fray. “It's typical Obama,” said presidential historian Douglas Brinkley, “he's trying to be the cerebral political thinker.”
Last year, in May, when he announced a new partnership with Netflix, he revealed he and Michelle’s production company would be called Higher Ground. In July, just after Trump and Vladimir Putin met in Helsinki, Obama gave his most extensive public remarks, the annual Mandela Lecture, in Johannesburg, and his subject was the populist backlash to globalization, which he said, “first came from the left but then came more forcefully from the right.” He never mentioned Trump by name.
In that speech, while cataloging the litany of authoritarian trends and making obvious references to the ways that he believes Trump has debased American politics, nonetheless his prescription was defined by anti-radicalism. He decried equally “unregulated, unbridled, unethical capitalism” and “old-style command-and-control socialism” in favor of traditional American liberalism, “an inclusive market-based system.” In case he wasn’t clear that populist demagoguery can come from either ideological direction, he added, “So those who traffic in absolutes when it comes to policy, whether it’s on the left or the right, they make democracy unworkable.”
This clinical detachment was on display the following day as well, when he hosted a town hall event for his foundation. Obama was asked by a young woman from Cameroon about how he decided on which political party to join. Obama’s answer was broad and sweeping in its view of America’s two parties and barely hinted at the common view among Democrats that the Republican Party under Trump is a radical outlier that should be vilified.
“In the United States,” Obama said, speaking in the slow and deliberate style that was the basis for comics who mimicked him, “there was a time where I might have been a Republican because Abraham Lincoln was a Republican. And at that time it was the Republican Party that was opposing the expansion of slavery in the United States. Today, it’s the Democratic Party that reflects the values that I spoke about at the Mandela Lecture yesterday. And that doesn’t necessarily mean that will always be the case. It doesn’t mean that in every instance I have agreed with the Democratic Party platform, but broadly speaking, when you look at who’s been concerned about broad-based economic growth, who’s been concerned about civil rights, who has been most supportive in making sure that women are treated fairly in the workplace, who’s supported collective bargaining, who has been most concerned with environmental issues, including climate change. Right now, that happens to be the Democratic Party. And again, that wasn’t always the case. There used to be more variation and different ideological views even within the parties so you might have more flexibility.”
This odd tangent, delivered by someone with less impeccable progressive credentials, might be attacked from the left as a kind of false equivalence, a statement about the two parties that is so abstract that it drains the very real differences between them today. But one way to make sense of it, as well as his “whether it’s on left or the right” warning of the day before, is that Obama has come to see the threat to stability differently now: Although the peril is more acute today from the right, his own party needs to be on guard against an absolutism rising on the left, which also happens to be the source of the attacks on his own legacy.
‘The Biden people ask, “Why won’t Obama say something”?’
Obama stayed away from campaign politics at the start of his post-presidency, but by the fall of 2018, when a wave was building and hundreds of his former administration officials were running for office, he dove in headfirst, endorsing dozens of candidates, a group from across the country that he described in non-ideological terms as “diverse, patriotic, and bighearted.” He focused on races that would help Holder’s redistricting project and many swing areas where party leaders knew he would be an asset.
According to several people close to him, his experience campaigning during 2018 made him even more convinced that Democrats had to be careful not to mistake the passion and excitement on Twitter for candidates like Alexandria Ocasio-Cortez for where the public was ideologically, especially in the coming general election against Trump.
A close family friend told me, “Remember he ran to the right of Hillary in 2008 on a lot of issues, and because he happened to be young and new on the scene and he happened to be African American, people just assumed that he would be running as a community organizer. And the reality is, on many issues he was running equal to or to the right of her. His politics are not strong left of center. I mean it's left, but he's nowhere near where some of the candidates are currently sitting, at least when he got himself elected.”
A close Obama adviser added: “There's a whole big country out there, so don’t just go to a rally and everybody's cheering and you think that that's always the pulse of the country. Those are just the people who showed up to hear you.”
While Trump’s early assault on American political norms created a cottage industry of “Where’s Obama?” outcry on the left, Obama’s own view, perhaps a bit self-serving, was that the more he became the face of his party, the less of a chance it allowed for new faces to emerge. And once the Democrats took over the House and the enormous Democratic presidential field began to emerge, the demands for him to weigh in on everything receded. These days when his staff brings him ideas, issues, outrages that he might address, Obama always asks a simple question, “To what end?” More often than not, he stays mum.
And then Joe Biden announced he would run for president. Presidents have always struggled with how much to support their vice presidents. At one level, a Biden win would be a profound vindication, an almost direct restoration of the Obama administration. But Obama had already passed over Biden for Hillary Clinton in 2016. With Biden out of the race in 2020, the psychodrama of their relationship and the intrigue about Obama’s assessment of Biden could have been avoided. Obama’s commitment to non-interference would have seemed less fraught.
Biden, Obama told people close to him before Biden even entered the race, would have to “earn” it. There would be no endorsement. (Biden has said he never asked for one.) Besides, he liked to say, fighting it out in a tough primary is what made Obama a strong candidate for the general election.
Last year, Obama let it be widely known that he would not make his preference known or, in the phrase that his close advisers frequently use, “put his thumb on the scale.” It wasn’t just Biden who was disappointed. Holder was particularly wounded that his close friend wasn’t more encouraging of his own ambitions. ”He’s still pretty sensitive about it,” said someone close to Holder. “He was really frustrated about having arrived at the decision not to run. Holder couldn’t get in because Biden and Holder have the same set of people. Once Biden was getting in then Eric couldn’t get in. So that frustrated Holder. It blocked him. And Biden has turned out the way they all feared, and that’s really frustrating to Eric.”
Over the past year, Obama and his closest advisers were clinical in their assessments of the candidates. They discussed doubts about Kamala Harris’ appeal to African Americans. Obama was deeply skeptical about the prospects of Mayor Pete Buttigieg. During their West End meeting, he was complimentary about Steve Bullock’s record as a governor and frank about his challenges: “Nobody knows who you are,” he told him.
When it comes to Sanders, I asked one close adviser whether Obama would really lay himself on the line to prevent a Sanders nomination. “I can’t really confirm that,” the adviser said. “He hasn’t said that directly to me. The only reason I'm hesitating at all is because, yeah, if Bernie were running away with it, I think maybe we would all have to say something. But I don't think that's likely. It's not happening.” (Another close Obama friend said, “Bernie's not a Democrat.”)
As for Warren, the candidate who has tried to bridge the worlds of Sanders and Obama, Obama’s relationship with Warren is famously complicated. Back in early 2015, when Warren was considering running for president and started to excite progressives, Obama said privately that if Democrats rallied around her as their nominee it would be a repudiation of him—a clear sign that his economic decisions after the Great Recession had been seen as inadequate. There are very few former senior Obama officials in Warren’s campaign.
The Obama diaspora is most heavily represented in Biden’s campaign. While Obama may have been cutting about Biden’s feel for the electorate, people close to him suggest that Obama, like many other Democrats who are clear-eyed about Biden’s weaknesses, has been surprised by his resilience.
“So many scenarios here are dependent on this idea that Biden is going to collapse,” said former Obama adviser David Axelrod, who has occasionally been withering about Biden’s campaign. “But he continues to have pretty strong appeal to African Americans and to working-class whites. What happens to those working-class whites? I mean is [Michael] Bloomberg really the default candidate for noncollege educated white voters? Is Deval? Or any of them? Maybe Amy [Klobuchar], but I honestly don't think she's getting out of Iowa. So the Biden thing is the strangest thing I've ever seen in politics because the guy is up there in the air and everybody is just assuming he's going to come down. There is kind of a Mr. Magoo kind of quality to the whole thing but he's still driving, you know? He's still moving forward. You worry that he's going to hit the wall at any given moment, but he hasn’t.”
One person who is very close to both Obama and Biden said the only time the Biden campaign has been disappointed in Obama is over Trump’s Ukraine scandal. “I don't think anybody in the Biden world challenges Obama’s affection for Biden, or challenges his strategy of not weighing in for anybody,” this person said. ”I do think there's frustration when Joe Biden and Hunter Biden get attacked by Republicans on the Ukrainian thing and they say, ’Obama and his administration looked the other way back when this was happening,’ and Obama doesn't say anything. The Biden people ask, ‘Why won’t Obama say something?’”
‘Who do we get along with a hundred percent? Nobody.’
Obama’s aides think of his voice as like a cannon. Because he so rarely speaks, especially about the nitty-gritty of 2020 politics, when he does go public, there is an enormous boom. He fired it on November 15, at an event in Washington for the Democracy Alliance, the network of wealthy progressive donors, during a question-and-answer session with Stacey Abrams.
“I don't take it as a criticism when people say, ’Hey, it's great, Obama did what he did and now we want to do more,’” Obama said. ”I hope so. That's the whole point.”
But he went on to deliver a line that was taken as a stinging criticism of Warren. He said Democrats should not be “deluded” that “resistance” to “bold” proposals will just melt away or that it’s the result of “false consciousness.” America, he said, is “less revolutionary than it is interested in improvement.” He was particularly pointed about immigration policies that went too far left, and suggested that adopting a policy to decriminalize the border, as Warren has, was deadly. “You go survey the average Democrat and they still think there's such a thing as a border,” he said. “And if you don't speak to those values, then you may be in for a rude shock.” He advised candidates not to confuse “left-leaning Twitter feeds” for the real electorate, and said “the average American doesn't think we have to completely tear down the system and remake it.”
According to his advisers, Obama thought he was offering up equal rebuke to both the Warren wing and the Biden wing in the primaries. The message to Biden was that he shouldn’t coast on Obama’s legacy, or attack Warren if she criticizes it.
Nobody who knows Obama well or who has been following him closely since he left office was surprised by what he said. One of his closest advisers said he was trying to give Warren some room on her “Medicare for All” proposal. “It wasn't about who he favors, it was about, ’let me give you all some advice from my experience about what wins,’” the adviser said. “That's not saying Elizabeth shouldn't be the nominee, because you know what? Maybe she emerges and we can't let one issue determine whether or not you support a person either. Who do we get along with a hundred percent? Nobody. I do think it gives permission for candidates to wiggle away from a hard and fast position if they want. If you know the most popular person in the party says it's OK to be a little bit more moderate, maybe that gives you some permission.”
Another adviser added, “I don’t think he was trying to benefit Biden here. Buttigieg benefits from this too. Knowing Obama as well as I do, he doesn’t want to help anyone or hurt anyone, he just wants to win the 2020 election.”
When I asked Holder who he thought Obama supports, he said, “As I talked to him, I'm not sure that I can honestly say that he has a particular candidate who he would at this point say that he’d vote for.”
‘He’s an extraordinarily self-confident guy’
In August, the Obamas’ Higher Ground production company released its first project, a Netflix documentary called American Factory. The film is about a Chinese conglomerate, Fuyao Glass Industry Group, that in 2014 bought a recently shuttered GM factory in Dayton, Ohio. The filmmakers, Julia Reichert and Steven Bognar, secured exceptional access to the company, both in the U.S. and China, from factory floor machinists all the up to the company’s chairman, Chinese billionaire Cho Tak Wong. When Fuyao’s American outpost struggles to make money, despite paying many former GM employees half of what they were previously making, he fires the local American leadership he had pledged would run the company, crushes a unionization effort by the United Auto Workers, and starts automating the assembly line. The company becomes profitable.
The film, which is already on some Oscar lists, was mostly finished when Higher Ground bought it, but Obama was involved in reviewing edits. In different hands the movie could have easily been a more forceful jeremiad about globalization and union-busting. Instead it strives to achieve a respectful and empathetic point of view for even the most villainous characters, like Wong who is shown, back in China, praying, reminiscing about his hardscrabble childhood, and second-guessing his life choices. In an unnerving scene toward the end of the movie, after the UAW has been defeated and new Chinese managers installed, Wong tours the Ohio factory while an aide points to American employees who will soon be fired and replaced by robots.
In a conversation released to promote the film, Reichert told Obama that she and Bognar don’t do “muckraking,” movies and American Factory’s nuanced portrayal has been pilloried from the socialist left. Jacobin, the pro-Sanders journal, lamented that the movie “reduces the class conflict in the plant to apolitical ‘storytelling’ — where no one is at fault and we are all bound by impersonal economic forces — and ‘culture clashes.’”
To Obama, this was a feature, not a bug. “I think one of the things that makes the movie powerful is the fact that it’s not all black and white,” he said in the film’s promo. “There’s a bunch of gray.”
Over the next year, Obama, according to his closest advisers, will start to emerge with slightly bolder colors. The boldest might be riding into a battle unfolding on his own side, if he did lead a potential stop-Bernie campaign. But absent that unlikely development, one adviser suggested that Obama could also be pulled into the primary and forced to play a major role if Democrats failed to pick a nominee before the convention. “The only kind of wrench in this, and I have not discussed this with him, is like what happens if we have a brokered convention?” the adviser said.
The ultimate test of whether Obama has successfully navigated his unexpectedly fraught post-presidency—the era of being caught between Trump and Biden and the rising left—will be whether Democrats win next year, when Obama is expected to fully reemerge as a partisan and campaign against Trump. He knows that’s when he will be expected to finally offer the full-throated case against his successor.
One close adviser remarked that Obama actually enjoyed the backlash and debate that his recent comments created and that he was eager to help quarterback the campaign against Trump next year. “As we all know, he’s an extraordinarily self-confident guy,” he said.
There was a hint of this recently. At one point in the interview with the directors of American Factory, Barack, sounding like a former star who had deftly left the audience wanting more, turns to Michelle, and says with a chuckle, “We still got a little pull, you know?”