A 'clown' who wouldn't go away: Inside Obama's team’s blind spot on Trump

For eight years, President Barack Obama's aides marveled that no amount of mockery, dismissal or scandal could make Donald Trump go away.

Their bewilderment is threaded through hundreds of interviews with administration officials released Tuesday in a far-reaching oral history of the Obama presidency. Throughout, Obama's advisers — some of the nation’s most accomplished political and policy experts — described their ongoing education about an electorate increasingly influenced by whatever the nascent social media told them.

Taking Trump's 2016 election victory 'personally'

Over two terms in the White House, they got glimpses of a future in which conspiracy theories, such as the lie that Obama was born outside the United States, survived online. What they missed, right up to Election Night 2016, was Trump's political resilience and his understanding that alienated Americans could vote for a man the White House considered a “clown.”

“He's done,” David Simas, Obama's White House political director, recalls telling the president. It was October 2016, five weeks before Election Day, and Simas had just handed his phone to Obama to watch the explosive news of Trump's “Access Hollywood” recording. Fast-forward to hours before voters went to the polls. Simas recognized Democrat Hillary Clinton's lead had shrunk to perhaps three points. “She’s fine,” he recalls thinking. “That’s the night before.”

Trump defeated Clinton in the Electoral College by 306 to Clinton's 232 but lost the popular vote, an outcome long known to have stunned and devastated Democrats. But the interviews filled in the degree to which aides, pollsters and news outlets disregarded the prospect of a Trump victory 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.”

Navigating the birther conspiracy theory

Across the Obama Presidency Oral History project's interviews with 450 people, his advisers said that Trump rebuked what they saw as the administration's accomplishments: An emergency rescue of the economy, a bailout of the auto industry, a form of national health insurance and landmark climate change regulation. All along, many described climbing a learning curve on how young and old Americans get their news, red and blue “team” politics — and how to leverage social media, something Trump seemed to innately understand.

An extraordinary stretch that began in April 2011 illustrated the denial, the dismissal and what's thought to have been a moment that helped cement Trump's decision to run for president.

The New York mogul had been fueling the false conspiracy theory that Obama, who was born in Hawaii, had not been born in the United States. That suggested he was not qualified to be president, a question that touched on Obama's race. It bothered him personally, advisers said, and initially Obama agreed with many advisers to ignore it.

“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'd been born in Hawaii.

“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,” Nancy-Ann DeParle, a former White House deputy chief of staff for policy.

Obama's ‘cathartic’ response

What it meant for speechwriter Jon Favreau was that Obama's jokes for the White House Correspondents Dinner just a few days later had to be changed. 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 that it was not just damaging to Obama but damaging to the country.”

Seriousness aside, he described a marathon of joke-writing with Hollywood director and writer Judd Apatow on the phone that left Favreau and others in hysterics. The prospect of Trump becoming president? “Not even a brief moment did I ever think that,” he said.

As for the speech, Obama “loved it,” Favreau said. Obama's sense of humor, he noted, can lean sarcastic.

Obama opened with a cheery, “Mahalo!” and played a mock birth video in a dig at Fox News.

“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.”

Then he noted that “Donald Trump is here tonight!” Trump glowered from his table.

"We all know about your credentials and breadth of experience,” Obama continued, as the Washington glitterati snickered. Just recently on Trump's 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.” Whom to fire in such a situation, Obama said sarcastically, was among “the kind of decisions that would keep me up at night.”

The next day, Obama announced the killing of Sept. 11 mastermind Osama bin Laden during a U.S. commando raid in Pakistan. He'd authorized the strike earlier in the week without the knowledge of most close aides, and so knew about it as he relished his takedown of Trump.

“In some ways, it was cathartic for the president,” Axelrod said of the speech.

Earlier in the evening, he recalled, he walked by Trump's table and overheard him saying he's toying with running for president. Axelrod “chuckled at it and went to my seat.”

“Obviously, we misread that,” he said.