Inside Obama’s advisers’ blind spot on Trump
Former and current aides describing the Obama presidency in a new oral history account say their internal understanding of Trump was shaped by what they believed should have ended his candidacy. They describe an extended period in which, despite ridicule and controversy, Trump did not fade—something they said left them bewildered about how an electorate increasingly influenced by online content could view him differently than the Obama White House did.
The account, released Tuesday, threads those observations through hundreds of interviews with administration officials about what they were learning over eight years in office. Several advisers and policy figures, the oral history suggests, were tracking both political behavior and how voters processed information, while underestimating the ability of conspiracy theories to survive outside the White House’s preferred frame.
David Simas, who served as Obama’s White House political director, described a moment in October 2016 when he said he told Obama, “He’s done,” about Trump. Simas said he had given Obama his phone so the president could watch developments from the “Access Hollywood” recording, and he added that he later viewed Hillary Clinton’s lead as having narrowed to perhaps three points before the election. In Simas’s recounting, he also looked at the timing—“That’s the night before”—as evidence that the race still should have broken toward Clinton.
Josh Earnest, a former White House press secretary, said it felt personal for Democrats as the election approached. Earnest said, “Not many people even expected that he had a chance to win,” and he added that it was “hard not to take it personally” because of what Trump represented to the Obama campaign—its opponents’ view of him and the way he carried himself, campaigned, and used rhetoric that advisers said conflicted with what they said the Obama era stood for.
The oral history also describes how aides wrestled with misinformation, including birther allegations that President Barack Obama was born outside the United States. Over the Obama Presidency Oral History project’s interviews with 450 people, advisers said Trump rebuked what they considered accomplishments of the administration, from what they described as help for the economy and auto industry through to efforts including national health insurance and landmark climate change regulation. At the same time, they said they watched how conspiracy narratives—such as the claim that Obama was not qualified because of birth—remained present in political discussion.
Advisers tied a stretch beginning in April 2011 to a wider lesson about the way such claims could persist. They said Trump had been fueling the false conspiracy theory about Obama’s birthplace, which advisers said touched on Obama’s race and that Obama initially agreed with some advisers to ignore it. David Axelrod, then a senior adviser, recalled that Obama felt the issue was “stupid and shouldn’t be dignified,” but he said the president concluded it “had to be.”
The oral history describes the White House’s response in April 2011, when Obama released a long-form birth certificate showing he was born in Hawaii. Nancy-Ann DeParle, a former deputy chief of staff for policy, said, “I thought it was a mistake at the time,” because she said she believed the question was absurd and beneath the presidency. DeParle’s recollection emphasized that she viewed it as unnecessary to dignify the issue.
That sequence, advisers said, carried forward into the White House correspondents’ dinner shortly afterward, as aides said they had to adjust plans and the tone of jokes. Jon Favreau, a speechwriter, said he saw what Trump was doing as racist, and he described writing jokes in coordination with Hollywood director and writer Judd Apatow after Trump’s presence was confirmed. Favreau said he and others did not treat Trump’s participation as light, even as the event demanded humor, and he said the speech had to address the birther storyline in a way that did not turn it into a serious endorsement of the conspiracy.
Favreau also recalled the “marathon of joke-writing” with Apatow on the phone, describing a call that left him and others in hysterics. He said he never believed, even briefly, that Trump would become president. When it came to the speech itself, Favreau said Obama “loved it” and noted that Obama’s sense of humor could lean sarcastic; Obama’s remarks included a mock dismissal aimed at Fox News and a line that explicitly told the Fox News table that what the president was using was a joke—“That was a joke,” Obama said, and he added, “That was not my real birth video. That was a children’s cartoon.”
In the account, Obama’s remarks also played to the moment of political tension in the room, with the president turning to Trump’s presence at the dinner. The narrative includes Obama saying, “Donald Trump is here tonight!” and describing the kinds of satirical references that followed, including sarcasm about credentials and the “kind of decisions” that would “keep me up at night.” Axelrod later said the speech was “cathartic” for the president, and he recalled walking by Trump’s table earlier in the evening.
Axelrod said he overheard Trump saying he was “toying with running for president,” and Axelrod said he “chuckled at it” before returning to his seat. In the oral history’s closing of that thread, Axelrod said, “Obviously, we misread that,” describing a turning point advisers said they did not anticipate—despite watching Trump’s persistence long before Election Night 2016.