Just after Donald J. Trump was elected president, Barack Obama slumped in his chair in the Oval Office and addressed an aide standing near a conspicuously placed bowl of apples, emblem of a healthy-snacking policy soon to be swept aside, along with so much else.
“I am so done with all of this,” Mr. Obama said of his job, according to several people familiar with the exchange.
Yet he knew, even then, that a conventional White House retirement was not an option. Mr. Obama, 55 at the time, was stuck holding a baton he had wanted to pass to Hillary Clinton, and saddled with a successor whose fixation on him, he believed, was rooted in a bizarre personal animus and the politics of racial backlash exemplified by the birther lie.
“There is no model for my kind of post-presidency,” he told the aide. “I’m clearly renting space inside the guy’s head.”
Which is not to say that Mr. Obama was not committed to his pre-Trump retirement vision — a placid life that was to consist of writing, sun-flecked fairways, policy work through his foundation, producing documentaries with Netflix and family time aplenty at a new $11.7 million spread on Martha’s Vineyard.
Still, more than three years after his exit, the 44th president of the United States is back on a political battlefield he longed to leave, drawn into the fight by an enemy, Mr. Trump, who is hellbent on erasing him, and by a friend, Joseph R. Biden Jr., who is equally intent on embracing him.
The stakes of that re-engagement were always going to be high. Mr. Obama is nothing if not protective of his legacy, especially in the face of Mr. Trump’s many attacks. Yet interviews with more than 50 people in the former president’s orbit portray a conflicted combatant, trying to balance deep anger at his successor with an instinct to refrain from a brawl that he fears may dent his popularity and challenge his place in history.
That calculus, though, may be changing in the wake of George Floyd’s killing by the police in Minneapolis. As America’s first black president, now its first black ex-president, Mr. Obama sees the current social and racial awakening as an opportunity to elevate a 2020 election dictated by Mr. Trump’s mud-wrestling style into something more meaningful — to channel a new, youthful movement toward a political aim, as he did in 2008.
He is doing so very carefully, characteristically intent on keeping his cool, his reputation, his political capital and his dreams of a cosseted retirement intact.
“I don’t think he is hesitant. I think he is strategic,” said Dan Pfeiffer, a top adviser for over a decade. “He has always been strategic about using his voice; it’s his most valuable commodity.”
Mr. Obama is also mindful of a cautionary example: Bill Clinton’s attacks against him in 2008 backfired so badly that his wife’s campaign staff had to scale back his appearances.
Many supporters have been pressing him to be more aggressive.
“It would be nice, for a change, if Barack Obama could emerge from his cave and offer — no wait, DEMAND — a way forward,” the columnist Drew Magary wrote in a much-shared Medium post in April titled “Where the Hell is Barack Obama?”
The counterargument: He did his job and deserves to be left alone.
“Obama has now been out of office for three and a half years, and he is still facing this kind of scrutiny — no one is pressuring white ex-presidents like George W. Bush and Jimmy Carter the same way,” said Monique Judge, news editor of the online magazine The Root and author of a 2018 article arguing that Mr. Obama no longer owed the country a thing.
Mr. Obama’s head appears to be somewhere in the middle. He is not planning to scrap his summer Vineyard vacation and is still anguishing over the publication date of his long-awaited memoir. But last week he stepped up his nominally indirect criticism of Mr. Trump’s administration — decrying a “shambolic, disorganized, meanspirited approach to governance” during an online Biden fund-raiser. And he made a pledge of sorts, telling Mr. Biden’s supporters: “Whatever you’ve done so far is not enough. And I hold myself and Michelle and our kids to that same standard.”
On Thursday, during an invitation-only Zoom fund-raiser, Mr. Obama expressed outrage at the president’s use of “kung flu” and “China virus” to describe the coronavirus. “I don’t want a country in which the president of the United States is actively trying to promote anti-Asian sentiment and thinks it’s funny. I don’t want that. That still shocks and pisses me off,” Mr. Obama said, according to a transcript of his remarks provided by a participant in the event.
Mr. Obama speaks with the former vice president and top campaign aides frequently, offering suggestions on staffing and messaging. Last month, he bluntly counseled Mr. Biden to keep his speeches brief, interviews crisp and slash the length of his tweets, the better to make the campaign a referendum on Mr. Trump and the economy, according to Democratic officials.
He has taken a particular interest in Mr. Biden’s work-in-progress digital operation, the officials said, enlisting powerful friends, like the LinkedIn founder Reid Hoffman and the former Google chief executive Eric Schmidt, to share their expertise, they said.
Yet he continues to slow-walk some requests, especially to headline more fund-raisers. Some in Mr. Obama’s camp suggest he wants to avoid overshadowing the candidate — which Mr. Biden’s people aren’t buying.
“By all means, overshadow us,” one of them joked.
‘Obama Will Not Be Able to Rest’
From the moment Mr. Trump was elected, Mr. Obama adopted a minimalist approach: He would critique his policy choices, not the man himself, following the norm of civility observed by his predecessors, especially George W. Bush.
But norms are not Mr. Trump’s thing. He made it clear from the start that he wanted to eradicate any trace of Mr. Obama’s presence from the West Wing. “He had the worst taste,” Mr. Trump told a visitor in early 2017, showing off his new curtains — which were not terribly different from Mr. Obama’s, in the view of other people who tramped in and out of the office during that chaotic period.
The cancellation was more pronounced when it came to policy. One former White House official recalled Mr. Trump interrupting an early presentation to make sure one staff proposal was not “an Obama thing.”
During the transition, in what looks in hindsight like a preview of the presidency, one Trump aide got the idea of printing out the detailed checklist of Mr. Obama’s campaign promises from the official White House website to repurpose as a kind of hit list, according to two people familiar with the effort.
“This is personal for Trump; it is all about President Obama and demolishing his legacy. It’s his obsession,” said Omarosa Manigault Newman, an “Apprentice” veteran and, until her abrupt departure, one of the few black officials in Mr. Trump’s West Wing. “President Obama will not be able to rest as long as Trump is breathing.”
When the two men met for a stilted postelection sit-down in November 2016, the president-elect was polite, so Mr. Obama took the opportunity to advise him against going scorched-earth on Obamacare. “Look, you can take my name off of it; I don’t care,” he said, according to aides.
Mr. Trump nodded noncommittally.
As the transition dragged on, Mr. Obama became increasingly uneasy at what he saw as the breezy indifference of the new president and his inexperienced team. Many of them ignored the briefing binders his staff had painstakingly produced at his direction, former Obama aides recalled, and instead of focusing on policy or the workings of the West Wing, they inquired about the quality of tacos in the basement mess or where to find a good apartment.
As for Mr. Trump, he had “no idea what he’s doing,” Mr. Obama told an aide after their Oval Office encounter.
Jared Kushner, Mr. Trump’s son-in-law and close adviser, made an equally indelible impression. During a tour of the building he abruptly inquired, “So how many of these people are sticking around?”
The answer was none, his escort replied. (West Wing officials serve at the president’s pleasure, as Mr. Trump would amply illustrate in the coming months.)
When the Kushner story was relayed to Mr. Obama, aides recalled, he laughed and repeated it to friends, and even a few journalists, to illustrate what the country was up against.
A White House spokesman did not deny the account, but suggested Mr. Kushner might have been talking about security and maintenance personnel rather than political appointees.
During other conversations with editors he respected, including David Remnick of The New Yorker and Jeffrey Goldberg of the Atlantic, Mr. Obama was more ruminative, according to people familiar with the interactions. At times, he would float some version of this question: Was there anything he could have done to blunt the Trump backlash?
Mr. Obama eventually came to the conclusion that it was a historic inevitability, and told people around him the best he could do was “set a counterexample.”
Others thought he needed to do more. During the transition, Paulette Aniskoff, a veteran West Wing aide, began assembling a political organization of former advisers to help Mr. Obama defend his legacy, aid other Democrats and plan for his deployment as a surrogate in the 2018 midterms.
He was open to the effort, but his eye was on the exits. “I’ll do what you want me to do,” he told Ms. Aniskoff’s team, but mandated they carefully screen out any appearances that would waste time or squander political capital.
Mr. Obama was, then as now, so determined to avoid uttering the new president’s name that one aide jokingly suggested they refer to him as “He-Who-Must-Not-Be-Named” — Harry Potter’s archenemy, Lord Voldemort.
Mr. Trump had no trouble naming names. In March 2017, he falsely accused Mr. Obama of personally ordering the surveillance of his campaign headquarters, tweeting, “How low has President Obama gone to tapp my phones during the very sacred election process. This is Nixon/Watergate. Bad (or sick) guy!”
It was an inflection point of sorts. Mr. Obama told Ms. Aniskoff’s team he would call out his successor by name in the 2018 midterms. But not a lot.
It was telling how Mr. Obama talked about Mr. Trump that fall: He referred to him less as a person than as a kind of epidemiological affliction on the body politic, spread by his Republican enablers.
“It did not start with Donald Trump — he is a symptom, not the cause,” he said in his kickoff speech at the University of Illinois in September 2018. The American political system, he added, was not “healthy” enough to form the “antibodies” to fight the contagion of “racial nationalism.”
The pandemic has, if anything, made him more partial to the comparison.
The virus, he said during his appearance with Mr. Biden last week, “is a metaphor” for so much else.
Golf Going ‘Better Than My Book’
Mr. Obama felt one of the best ways to safeguard his legacy was by writing his book, which he envisioned as both a detailed chronicle of his presidency and as a serious literary follow-up to his widely praised 1995 memoir, “Dreams From My Father.”
In late 2016, Mr. Obama’s agent, Bob Barnett, began negotiating a package deal for Mr. Obama’s memoir and Michelle Obama’s autobiography. Random House eventually won the bidding war with a record-shattering $65 million offer.
The process has been a gilded grind. One former White House official who checked in with Mr. Obama in mid-2018 was told the project “was like doing homework.”
Another associate, who ran into the former president at an event last year, remarked at how fit he looked. Mr. Obama replied, “Let’s just say my golf game is going a lot better than my book.”
It was not especially easy for the former president to look on as his wife’s book, “Becoming,” was published in 2018 and quickly became an international blockbuster.
“She had a ghostwriter,” Mr. Obama told a friend who asked about his wife’s speedy work. “I am writing every word myself, and that’s why it’s taking longer.”
The book’s timing remains among the touchiest of topics. Mr. Obama, a deliberate writer prone to procrastination — and lengthy digression — insisted that there be no set deadline, according to several people familiar with the process.
In an interview shortly after Mr. Obama left office, one of his closest advisers had predicted that the book would be out in mid-2019, before the primary season began in earnest, an option preferred by many working on the project.
But Mr. Obama did not finish and circulate a draft of between 600 and 800 pages until around New Year’s, too late to publish before the election, according to people familiar with the situation.
He is now seriously considering splitting the project into two volumes, in the hope of getting some of it into print quickly after the election, perhaps in time for the Christmas season, several people close to the process said.
Mr. Obama’s other big creative enterprise, a multimillion-dollar 2018 contract with Netflix to produce documentaries and scripted features with his wife, has been a tonic, and quick work by comparison.
Mr. Obama got a kick out of screening dozens of potential projects and offered specific suggestions — scrawled onto the yellow legal pad he used to write his book — to directors and writers. His production firm, Higher Ground Productions, is run out of a small bungalow on a Hollywood studio lot once home to Charlie Chaplin’s company, and he spent a day kibbitzing with its small staff during a visit in November.
One of the first efforts was “Crip Camp,” an award-winning documentary about a summer camp in upstate New York, founded in the early 1970s, that became a focal point of the disability rights movement.
Mr. Obama saw the project as a vehicle for his vision of grass-roots political change, and provided feedback during the 18 months the movie was in production.
“We saw footage that the filmmakers had just begun to cut together and sent it to the president to look at,” said Priya Swaminathan, co-head of Higher Ground. “He wanted to know how we could help the filmmakers make this the best telling of the story and they were into the collaboration. We watched many, many cuts together.”
A ‘Tailor-Made’ Moment
Part of what Mr. Obama finds so appealing about filmmaking is that it allows him to control the narrative. In that respect, the 2020 campaign has been a disorienting experience: His political career is supposed to be over, yet he has a semi-starring role in a production he has not written or directed.
Nowhere has that low-grade frustration been more apparent than in his complicated relationship with Mr. Biden, who is concurrently covetous of his support and fiercely determined to win on his own.
Mr. Obama was supportive of Mr. Biden, personally, from the start of the campaign, but he promised Senator Bernie Sanders, in one of their early chats, that his public profession of neutrality was genuine and that he was not working secretly to elect his friend, accoding to a party official familiar with the exchange.
Moreover, Mr. Obama has always been cleareyed about his friend’s vulnerabilities, urging Mr. Biden’s aides to ensure that he not “embarrass himself” or “damage his legacy,” win or lose.
When a Democratic donor raised the issue of Mr. Biden’s age late last year — he is 77 — Mr. Obama acknowledged those concerns, saying, “I wasn’t even 50 when I got elected, and that job took every ounce of energy I had,” according to the person.
Still, he is an enthusiastic supporter, and played a central role in pushing Mr. Sanders to “accelerate the endgame” that led to Mr. Biden’s earlier-than-expected victory in April. He spent the next few weeks tidying up a few messy political loose ends, working to improve his chilly relationship with Senator Elizabeth Warren, who irked him by criticizing his Wall Street speaking fees as emblematic of the scourge of money in politics, calling it a “snake that slithers through Washington.”
He has never seen Mr. Biden’s campaign as a proxy war between himself and Mr. Trump, his aides insist. But he is, nonetheless, tickled by the lopsided metrics of their competition of late.
Mr. Obama monitors their respective polling numbers closely — he gets privately circulated data from the Democratic National Committee — and takes pride in the fact that he has millions more Twitter followers than a president who relies on the platform far more than he does, people close to him said.
The former president devours online news, scouring The New York Times, The Washington Post and Atlantic sites on his iPad constantly, and keeps to his White House night-owl hours, sending texts and story links to friends between midnight and 2 a.m. Even during the pandemic he does not sleep late, at least on weekdays, and is often on his Peloton bike by 8 a.m., sending off a new round of texts, often about the latest Trump outrage.
Mr. Obama was already stepping up his criticism of Mr. Trump before Mr. Floyd’s killing in May. Ms. Aniskoff organized an online meeting with 3,000 former administration officials whose purpose, in part, was to soft-launch his tougher line. (Democrats close to Mr. Obama helpfully leaked the recording of his remarks.)
Yet the rising cries for racial justice have lent the 2020 campaign a coherence for Mr. Obama, a politician most comfortable cloaking his criticism of an opponent — be it Mrs. Clinton or Mr. Trump — in the language of movement politics.
Mr. Obama’s first reaction to the protests, people close to him said, was anxiety — that the spasms of rioting would spin out of control and play into Mr. Trump’s narrative of a lawless left.
But peaceful demonstrators took control, igniting a national movement that challenged Mr. Trump without making him its focal point.
Soon after, in the middle of a strategy call with political aides and policy experts at his foundation, an excited Mr. Obama pronounced that “a tailor-made moment” had arrived.
Mr. Obama has lately been in close contact with his first attorney general, Eric H. Holder Jr., sharing his outrage over the way the current attorney general, William P. Barr, personally inspected the phalanx of federal law enforcement officers who tear-gassed demonstrators to clear the path for Mr. Trump’s walk to a photo op at a historic church near the White House.
Mr. Holder has few qualms about calling Mr. Trump a racist in the former president’s presence. Mr. Obama has never contradicted him, but he avoids the term, even in private, preferring a more indirect accusation of “racial demagoguery,” according to several people close to both men.
His response to the Floyd killing was less about hammering Mr. Trump than about encouraging young people, who have been slow in embracing Mr. Biden, to vote. When he chose to speak publicly, it was to host an online forum highlighting a slate of policing reforms that went nowhere in his second term.
In that sense, the role he is most comfortable occupying is the job he was once so over.
On June 4, an hour or so before Mr. Floyd’s memorial service in Minneapolis, the former president called his brother, Philonise Floyd — a reprise of the calls he made to grieving families over his eight years in office.
“I want you to have hope. I want you to know you are not alone. I want you to know that Michelle and I will do anything you want me to do,” Mr. Obama said during the emotional 25-minute conversation, according to the Rev. Al Sharpton, who was on the call. Two other people with knowledge of the call confirmed its contents.
“That was the first time, I think, that the Floyd family really experienced solace since he died,” Mr. Sharpton said in an interview.
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