Obama Advisers Reflect on Underestimating Trump in Newly Released Oral History

For eight years, President Barack Obama’s aides marveled that no amount of mockery, dismissal or scandal could make Donald Trump go away. This bewilderment runs throughout hundreds of interviews with administration officials released Tuesday in a comprehensive oral history of the Obama presidency.

Throughout the interviews, Obama’s advisers—some of the nation’s most accomplished political and policy experts—described their ongoing education about an electorate increasingly influenced by social media. What became clear was how conspiracy theories, such as the false claim that Obama was born outside the United States, gained traction online and refused to die.

What these seasoned political professionals missed, even up to Election Night 2016, was Trump’s remarkable political resilience and his connection with alienated Americans who could vote for a man the White House dismissed as a “clown.”

“He’s done,” David Simas, Obama’s White House political director, recalls telling the president in October 2016, just five weeks before Election Day, after showing Obama the explosive “Access Hollywood” recording. Hours before voters went to the polls, Simas recognized Democrat Hillary Clinton’s lead had shrunk to perhaps three points but still thought, “She’s fine.”

Trump’s subsequent victory in the Electoral College—306 to Clinton’s 232, despite losing the popular vote—left Democrats stunned. The interviews reveal just how deeply Obama’s team had dismissed the possibility of a Trump presidency, even as Americans increasingly distrusted government and established political figures.

“Not many people even expected that he had a chance to win,” said former White House press secretary Josh Earnest. “It was hard not to take it personally, because Trump’s candidacy, the essence of his being, and everything that he stood for, and everything about the way that he carried himself, and everything that he championed, and his rhetoric, his campaign tactics—all were anathema to everything that the Obama campaign and the Obama era, the Obama administration, had been about.”

The oral history project, which includes interviews with 450 people, portrays Trump as a repudiation of what Obama’s team viewed as their accomplishments: economic recovery measures, the auto industry bailout, the Affordable Care Act, and landmark climate change regulations. Throughout the interviews, advisers described their learning curve regarding how Americans consume news, partisan “team” politics, and the power of social media—a platform Trump seemed to intuitively understand.

A pivotal moment came in April 2011 when Trump was actively promoting the false “birther” conspiracy theory questioning Obama’s U.S. birth. Initially, Obama preferred to ignore these claims.

“He felt with all the important things that needed to be dealt with, this was stupid and shouldn’t be dignified. But ultimately, it had to be,” recalled David Axelrod, then Obama’s senior adviser.

Obama released his long-form birth certificate on April 27, showing he was born in Hawaii. Nancy-Ann DeParle, a former White House deputy chief of staff for policy, believed this was a mistake: “I thought, ‘This is absurd, and it’s unnecessary and beneath him to dignify the question.'”

Days later came the White House Correspondents’ Dinner, where Obama delivered a blistering comedic takedown of Trump, who sat stony-faced in the audience. Speechwriter Jon Favreau recalled working with Hollywood director Judd Apatow on jokes that left the writing team in hysterics. The possibility of Trump becoming president never crossed his mind.

“Obama “loved it,” Favreau said of the speech, noting the president’s tendency toward sarcasm. Obama mocked Trump’s “credentials and breadth of experience,” referencing his reality show “The Apprentice” and suggesting that firing contestants at a steakhouse represented “the kind of decisions that would keep me up at night.”

What made the moment even more remarkable was that Obama knew something almost no one else in the room did—he had already authorized the raid that would kill Osama bin Laden the following day.

“In some ways, it was cathartic for the president,” Axelrod said of the speech. Earlier that evening, Axelrod had walked past Trump’s table and overheard him discussing a potential presidential run. Axelrod “chuckled at it and went to my seat.”

“Obviously,” he concluded in hindsight, “we misread that.”