Inside Team Obama’s Blind Spot on Trump

For eight years, President Barack Obama’s advisers marveled that no amount of ridicule, impeachment or scandal could make Donald Trump go away.

Their bewilderment is conveyed through hundreds of interviews with administration officials released Tuesday in a sweeping oral history of the Obama presidency. Over time, Obama’s advisers — some of the nation’s most accomplished political and policy experts — described their continuing education about an electorate increasingly swayed by whatever burgeoning social media told them.

Taking Trump’s 2016 election victory “personally”.

During two terms in the White House, they envisioned a future in which conspiracy theories, such as the lie that Obama was born outside the United States, survived online. What they missed, until election night in 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, told the president. It was October 2016, five weeks before Election Day, and Simas had just handed the phone to Obama to follow the breaking news of Trump’s “Access Hollywood” taping. Fast forward a few hours before voters go to the polls. Simas admitted that Democrat Hillary Clinton’s lead had narrowed to three points. “That’s good,” he remembers thinking. “That’s the night before.”

Trump defeated Clinton in the Electoral College 306 to Clinton’s 232, but lost the popular vote, a result that is known to have stunned and devastated Democrats. But the interviews underscored the degree to which advisers, pollsters and news outlets were dismissive of the prospect of a Trump victory, even as Americans increasingly distrusted the government and established political figures.

“Not many people even expected to have 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 he stood for, and everything about the way he carried himself and everything he stood for, and his rhetoric, his campaign tactics — they were all anathema to everything that had been in the Obama campaign and the Obama era, the Obama administration.”

Navigating the Birth Conspiracy Theory

In Obama Presidency Oral History Project interviews with 450 people, his aides said Trump rebuked what they considered the administration’s accomplishments: an emergency bailout of the economy, a bailout of the auto industry, some form of national health insurance and landmark climate change regulation. Over time, many described climbing a learning curve about how Americans young and old get their news, red and blue “team” politics — and how to use social media, something Trump seemed to understand naturally.

An extraordinary stretch that began in April 2011 illustrated denial, impeachment and what is believed to have been a moment that helped solidify Trump’s decision to run for president.

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

“He felt that with all the important things that needed to be addressed, this was stupid and shouldn’t be dignified. But in the end, it had to be,” recalls David Axelrod, then a senior adviser to Obama.

Obama released his long-form birth certificate on April 27, showing he was born in Hawaii.

“I thought it was a mistake at the time because I thought, ‘This is absurd and unnecessary and beneath him to dignify the question,'” said Nancy-Ann DeParle, former deputy chief of staff for policy at the White House.

Obama’s ‘cathartic’ response

What that meant for speechwriter Jon Favreau was that Obama’s jokes for the White House Correspondents’ Dinner just 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 it was not only bad for Obama, but bad for the country.”

All seriousness aside, he described a phone-in banter with Hollywood director and writer Judd Apatow that sent Favreau and others into hysterics. The prospect of Trump becoming president? “I didn’t think about it for a second,” he said.

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

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

“I want to clarify the Fox News table: It was a joke,” he said. “This wasn’t my actual birth video. It was a cartoon for kids.”

He then remarked that “Donald Trump is here tonight!” Trump looked up from his table.

“We all know about your credentials and the breadth of your experience,” Obama continued, as the Washington glitterati laughed. Recently on Trump’s show, the president said, “At the steakhouse, the all-male cooking team didn’t impress the judges at Omaha Steaks. And there was a lot of blame going around.” Who to fire in such a situation, Obama quipped, is among “the kind of decisions that would keep me up at night.”

The next day, Obama announced the killing of Osama bin Laden on 9/11 during a US commando raid in Pakistan. He had authorized the strike earlier in the week without the knowledge of his closest aides, and so he knew about it while he liked Trump’s ouster.

“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 heard him say he was toying with running for president. Axelrod “giggled and went to my seat.”

“Obviously I read it wrong,” he said.

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