THE NEW YORK TIMES: Obama took on recession, health care and Iraq. What he didn’t see coming was Trump

As President Barack Obama’s chief strategist, David Axelrod, made his way across a hotel ballroom on the night of the White House Correspondents’ Association dinner in 2011, he happened to overhear Donald Trump boasting to other guests. “I know it’s crazy,” Trump was saying, “but I’m in front of the polls.”

“I kind of chuckled at it and went to my seat,” Mr Axelrod recalled. “I don’t think any of us really anticipated that Donald Trump would be a serious candidate for president, much less president.”

It was later that same evening that Obama would mock Trump from the stage, ridiculing the reality television star in a moment that would go viral.

In fact, Obama and his team never saw Trump coming, as a new set of oral history interviews released Tuesday makes abundantly clear. He was, to them, a “con man,” a “clown,” a “laughingstock.”

He was a thorn in the side with his birther lies and demagogic bloviating. But as it turned out, Obama and his advisers, like many others, missed the shifting mood of the country that would ultimately upend Mr Axelrod’s assumptions.

The oral history, compiled by Incite Institute, a social science research centre at Columbia University, represents the most extensive set of interviews made public to date from the Obama presidency.

The institute, in cooperation with the Obama Foundation, conducted more than 450 interviews totalling more than 1100 hours of audio and video with Cabinet secretaries, White House aides, family members, opposition leaders and outside figures affected by administration policies.

Two limited tranches of the oral history interviews were released previously, but the institute posted the full set online Tuesday morning for the perusal of historians, researchers and the merely curious.

The interviews do not include Obama or his wife, Michelle Obama, or vice president, Joe Biden, but do include major figures such as Hillary Clinton, John F. Kerry, Robert M. Gates, Paul D. Ryan, Oprah Winfrey and even the former president’s mother-in-law, Marian Robinson, who died in 2024.

The interviews tell the back story of a presidency that pulled the country out of the worst economic crisis since the Great Depression; rescued the auto industry; passed landmark legislation on health care, LGBTQ+ rights and financial regulation; brought home most troops from Iraq; and hunted down and killed Osama bin Laden.

They also explore the failure to stop the Russian annexation of Crimea, the slaughter in Syria, the collapse of Libya and the rise of the Islamic State group.

But nine years after he left office with high approval ratings and one year into Trump’s second term, what remains striking is how inconceivable it seemed to Obama and his team that populist disenchantment with the establishment, globalisation and demographic changes would elevate a figure they scorned.

It was a question that hovered over the interviews as they struggled for answers.

“The outcome of the election was a direct rebuke of everything that we had been trying to do for the last 10 years,” reflected Josh Earnest, who was Obama’s last White House press secretary.

“Trump’s candidacy,” he added, “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.”

Mr Axelrod recounted that the first time he ever spoke with Trump was in 2010 during the BP oil leak in the Gulf of Mexico.

Trump reached out through Mika Brzezinski, one of the hosts of “Morning Joe” on MSNBC, to offer his services to plug the leak. Mr Axelrod thought it was preposterous and politely declined.

But when the spill was finally halted, Trump had another idea for Mr Axelrod. “I build ballrooms, I build the greatest — you can ask anybody, my ballrooms are the greatest ballrooms,” Trump told him by phone, as Mr Axelrod recalled.

“You have these state dinners, and you have them in these shitty little tents out in the backyard. Let me build a modular ballroom that you can assemble when you have state dinners so it’ll look good.”

Mr Axelrod thought that would be a bad signal in the midst of “this monstrous recession” and brushed him off. “I said: ‘Well, that’s really nice of you. I’m going to pass this on to the social secretary and I’ll have her call you,’” Mr Axelrod recalled. “I did. She didn’t.”

Nearly a decade later, Trump is now finally building his ballroom.

The decision to roast Trump at the 2011 correspondents’ dinner stemmed from aggravation over the continuing lies about Obama’s birthplace.

“I thought what he was doing was racist,” recalled Jon Favreau, the speechwriter who helped draft the remarks. “I thought and still do think that he is a ridiculous human being who deserves to be ridiculed at every possible chance.”

Mr Favreau and his colleagues came up with lines making fun of Trump’s “Celebrity Apprentice” television show.

“We gave it to Obama and he loved it,” Mr Favreau said. “He was so excited to do it.”

Did Mr Favreau think at the time that Trump might be a formidable presidential candidate? “Not even a brief moment did I ever think that.”

After the dinner, Mr Favreau said Trump approached Seth Meyers, the late-night comic who performed that night and also made fun of Trump.

“He told Seth: ‘That was very unfair what you did. It was very unfair.’” At the after-party, Mr Favreau said, he and Mr Meyers laughed at Trump. “We were like, ‘Wow, we really got him.’”

There are those who speculate that Trump’s red-faced fury that evening may have played a part in motivating him to run for president. He kicked off his campaign four years later, in June 2015.

“Nobody took it seriously at the time,” said Cody Keenan, another speechwriter for Obama.

Indeed, after Trump proposed banning Muslims from entering the United States, Mr Earnest dismissed the Republican candidate from the White House lectern.

“I talked about Donald Trump and his ideas being relegated to the dustbin of history,” Mr Earnest recalled. “I think I was kind of wrong about that unfortunately.”

Trump surged to the Republican nomination despite the Obama team’s expectations, but even then they assumed he could not beat Clinton in the general election.

Obama wanted to give a speech at the Democratic National Convention pushing back against the forces that Trump represented.

“At the time, I don’t think anybody thought Donald Trump was going to win,” Mr Keenan said.

“So it wasn’t aimed at him, and that’s because his party is the party that made it happen. None of this began with Donald Trump. These were trends that have been happening for a long time, stoking fear of the others, stoking misinformation, kind of this phony populism that turned people against each other.”

While more voters cast ballots for Clinton, making her the popular-vote winner, the Electoral College lined up for Trump, making him the president-elect. The White House was a dark place in the days that followed.

“There’s a pall over everything because you have no idea what the Trump stuff is going to be, and everything feels at risk,” said Denis McDonough, the last White House chief of staff for Obama.

“I feel like we accomplished what we set to accomplish. Except Trump won.”

This article originally appeared in The New York Times.

© 2026 The New York Times Company