For eight years, President Barack Obama’s aides marveled that no amount of ridicule, dismissal or scandal could make Donald Trump go away.
Their frustration is threaded through hundreds of interviews with administration officials released Tuesday in a far-reaching oral history of Obama’s presidency. During this period, Obama’s advisers — among the nation’s most skilled political and policy experts — described their ongoing education about the electorate as increasingly influenced by what the newly elected social media told them.
Taking Trump’s 2016 Election Victory ‘Personally’
Over two terms in the White House, they glimpsed a future in which conspiracy theories such as the lie that Obama was born outside the United States lived online. What they lost by election night 2016 was Trump’s political flexibility and his understanding that Americans abroad could vote for someone the White House considers a “clown.”
“He did,” David Simas, Obama’s White House political director, told the president. It was October 2016, five weeks before Election Day, and Seamus had just handed Obama his phone to watch the explosive news of Trump’s “Access Hollywood” recording. Fast-forward to a few hours before voters go to the polls. Seamus acknowledged that Democrat Hillary Clinton’s lead had narrowed to perhaps three points. “She was fine,” she recalls. “It’s the night before.”
Trump beat Clinton in the Electoral College by 306 to Clinton’s 232 but lost the popular vote, a result that has long shocked and devastated Democrats. But despite the degree to which aides, pollsters and news outlets downplayed the prospect of a Trump victory, Americans increasingly distrusted government and established political figures.
Former White House press secretary Josh Earnest said, “Most people didn’t even expect him to have a chance to win.” “It wasn’t hard to take it personally, because Trump’s candidacy, the very essence of his existence, and everything he stood for, and the way he carried himself, and everything he championed, and his rhetoric, his campaign strategy — everything was antithetical to the Obama campaign and the Obama era, everything that was about the Obama administration.”
Navigating the birther conspiracy theory
In interviews with 450 people from the Obama Presidency Oral History Project, his advisers said Trump rebuked what he saw as the administration’s achievements: the emergency rescue of the economy, the bailout of the auto industry, a form of national health insurance and landmark climate change regulations. All along, many described climbing a learning curve about how Americans young and old get their news, red and blue “team” politics — and how to take advantage of social media, something Trump seems to innately understand.
An extraordinary stretch that began in April 2011 featured denials, dismissals and what became the moment that helped cement Trump’s decision to run for president.
The New York mogul has been promoting a false conspiracy theory that Obama, who was born in Hawaii, was not born in the United States. It suggested he was unfit to be president, a question that dogged Obama’s run. This bothered him personally, advisers said, and at first Obama agreed to ignore many advisers.
“He felt the need to deal with all the important things, it was silly and not honorable. But ultimately, it had to be,” recalled David Axelrod, then a senior adviser to Obama.
Obama released his long-form birth certificate on April 27, stating that he was born in Hawaii.
“I thought it was a mistake, because I thought, ‘It’s absurd, and it’s unnecessary and it’s beneath him to honor this question,'” Nancy-Anne DeParle, former White House deputy chief of staff for policy.
Obama’s ‘cathartic’ response
What it meant to speechwriter Jon Favreau was to change Obama’s jokes for the White House Correspondents’ Dinner a few days later. They knew Trump would be at the dinner and the issues at hand, Favreau said in his interview, were serious. “I thought what he was doing was racist,” Favreau said. “I thought it would not only harm Obama but harm the country.”
All seriousness aside, he described a joke-writing marathon over the phone with Hollywood director and writer Judd Apatow that left Favreau and others in hysterics. The possibility of Trump becoming president? He said, ‘I didn’t even think like this.
As for the speech, Obama “loved it,” Favreau said. Obama’s sense of humor, he notes, can lean sarcastic.
Obama opened with a cheer, “Mahlo!” And a dig at Fox News playing a fake birth video.
“I want to make it clear to the Fox News table: That was a joke,” he said. “It wasn’t a video of my actual birth. It was a children’s cartoon.”
He then noted that “Donald Trump is here tonight!” Trump beamed from his desk.
“We all know the breadth of your credentials and experience,” Obama continued, drawing Washington’s surprise. At a recent Trump event, the president said, “At the steakhouse, the men’s cooking team didn’t impress the judges at Omaha Steaks. And there was a lot of blame to go around.” Who to fire in such a situation, Obama quipped, “is one of the decisions that keeps me up at night.”
The next day, Obama announced that 9/11 mastermind Osama bin Laden had been killed during a US commando raid in Pakistan. He had authorized the strike earlier in the week without the knowledge of several close aides, and Trump knew about it as he enjoyed his takedown.
“In some ways, it was cathartic for the president,” Axelrod said of the speech.
Earlier in the evening, he recalled, he had walked by Trump’s table and heard that he was playing for the presidency. Axelrod “laughed at this and went to my seat.”
“Obviously, we got that wrong,” he said.

