A comprehensive oral history featuring 450 interviews with Obama administration officials shows how they consistently underestimated Donald Trump's political potential. The interviews reveal their struggle to understand changing media landscapes and voter sentiment that ultimately led to Trump's 2016 victory.
Throughout Barack Obama’s eight-year presidency, his staff remained baffled by Donald Trump’s persistent presence in politics, unable to understand how ridicule, controversies, or dismissal failed to diminish his influence.
This confusion emerges clearly in a comprehensive oral history of the Obama administration made public Tuesday, featuring conversations with 450 former officials. The extensive interviews reveal how Obama’s team of seasoned political professionals struggled to grasp an evolving electorate shaped by emerging social media platforms.
During Obama’s two White House terms, his advisers witnessed the rise of online conspiracy theories, including false claims about the president’s birthplace, but failed to recognize Trump’s political staying power or his connection with disaffected voters whom the administration viewed as supporting a “clown.”
David Simas, who served as Obama’s White House political director, remembered confidently telling the president “He’s done” in October 2016, just five weeks before the election, after showing Obama the explosive “Access Hollywood” recording on his phone. Even on the eve of voting, with Hillary Clinton’s lead narrowed to approximately three points, Simas remained optimistic, thinking “She’s fine.”
Trump ultimately secured 306 electoral votes compared to Clinton’s 232, despite losing the popular vote – a result that devastated Democrats. The oral history interviews illuminate how extensively staff members, polling experts, and media organizations dismissed Trump’s victory chances while Americans grew increasingly skeptical of government and traditional political leaders.
Former White House press secretary Josh Earnest reflected on the widespread disbelief: “Not many people even expected that he had a chance to win. 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 Obama Presidency Oral History project interviews show how advisers felt Trump rejected their administration’s key achievements: economic recovery efforts, automotive industry rescue, healthcare reform, and significant environmental regulations. Many described learning how Americans across age groups and political affiliations consumed news and engaged with social media – areas where Trump demonstrated natural skill.
A pivotal period beginning in April 2011 exemplified the administration’s dismissive approach and potentially motivated Trump’s presidential ambitions.
Trump had been promoting the baseless conspiracy theory that Obama, actually born in Hawaii, was not a natural-born citizen and therefore constitutionally ineligible for the presidency – claims that carried racial undertones and personally affected Obama. Initially, the president followed advisers’ recommendations to ignore these allegations.
David Axelrod, then serving as Obama’s senior adviser, recalled the president’s initial reluctance: “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.”
On April 27, Obama publicly released his detailed birth certificate proving his Hawaiian birth.
Nancy-Ann DeParle, former White House deputy chief of staff for policy, disagreed with this decision: “I thought it was a mistake at the time, because I thought, ‘This is absurd, and it’s unnecessary and beneath him to dignify the question.'”
The birth certificate release forced speechwriter Jon Favreau to revise Obama’s upcoming White House Correspondents Dinner remarks. Knowing Trump would attend the event, Favreau took the situation seriously, stating in his interview: “I thought what he was doing was racist. I thought that it was not just damaging to Obama but damaging to the country.”
Despite the gravity, Favreau described an intensive joke-writing session with Hollywood director Judd Apatow that left the writing team laughing uncontrollably. The possibility of Trump reaching the presidency? “Not even a brief moment did I ever think that,” he admitted.
Obama enthusiastically approved the final speech, with Favreau noting the president’s tendency toward sarcastic humor.
Obama began his remarks with a cheerful “Mahalo!” and showed a humorous birth video mocking Fox News coverage.
“I want to make clear to the Fox News table: That was a joke,” he said. “That was not my real birth video. That was a children’s cartoon.”
He then acknowledged Trump’s presence: “Donald Trump is here tonight!” as Trump sat stone-faced at his table.
“We all know about your credentials and breadth of experience,” Obama continued while the Washington elite laughed. Referencing Trump’s reality show, the president said: “At the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around.” Obama sarcastically suggested that deciding “the kind of decisions that would keep me up at night” included whom to fire in such situations.
The following day brought Obama’s announcement of Osama bin Laden’s death during a U.S. special forces operation in Pakistan. He had approved the mission earlier that week without informing most close advisers, meaning he knew about the successful raid while delivering his Trump criticism.
Axelrod described the speech’s impact on Obama: “In some ways, it was cathartic for the president.”
Earlier that evening, Axelrod recalled walking past Trump’s table and overhearing him discuss potentially running for president. Axelrod “chuckled at it and went to my seat.”
“Obviously, we misread that,” he acknowledged.