President Barack Obama's administration underestimated President Donald Trump's political potential, viewing him as a 'con man' and 'clown'. Photo / Getty Images
It was an evening in April 2011, and then-United States President Barack Obama had just given the order to go ahead with the commando raid to kill Osama bin Laden when he took to a podium in a Washington hotel and grinned at Donald Trump.
“I know that he’s taken some flak lately, but no one is happier, no one is prouder to put this birth certificate matter to rest than the Donald,” the President quipped, citing Trump’s championing of a conspiracy theory that Obama had been born overseas and was thus ineligible to be President.
“And that’s because he can finally get back to focusing on the issues that matter – like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”
As Trump grew more annoyed, and Obama’s grin grew only wider, the speechwriter responsible for the mockery was revelling in the effect of his words.
“I was at the table behind Trump,” says Jon Favreau in one of hundreds of interviews with Obama-era officials released this week.
“I remember seeing the side of Trump’s face during the speech and seeing how angry he was.
“I thought and still do think that he is a ridiculous human being who deserves to be ridiculed at every possible chance,” he adds.
But “not even for a brief moment” did Favreau believe the target of his ire would prove to be a political force of nature.
Trump’s election victory, five years later, would prove that to be a massive misconception on the part of the young speechwriter.
But a vast tranche of documents and interviews related to the Obama presidency – newly released by a social science research centre at Columbia University in co-ordination with the Obama Foundation – show that Favreau was not alone.
More than 450 interviews with Obama-era officials, his relatives and political opponents have cast new light on how catastrophically the 44th US president – and others – failed to grasp the electoral threat posed by his eventual successor.
The interviews do not include testimony from Obama himself, his wife, Michelle, or then vice-president, Joe Biden. But they do involve key figures in his administration and wider political circle.
And they show that to many in Obama’s White House, Trump was nothing but a “conman”, “clown”, and a “laughing stock”.
So how did his administration, so focused on “change” and which regarded its own election as a landmark victory against the Washington status-quo, get it so badly wrong?
It started, it seems, with an outright – some would say arrogant – refusal to take Trump seriously.
Another moment from the 2011 correspondent’s dinner, captured in the oral history and made public by the Incite Institute, is particularly revealing.
David Axelrod, Obama’s chief strategist, recounts overhearing Trump saying: “I know it’s crazy … but I’m in front of the polls”.
“I kind of chuckled at it and went to my seat,” Axelrod says. “I don’t think any of us really anticipated that Donald Trump would be a serious candidate for president, much less president.”
The puzzling thing, according to US pollster Bruce Stokes, an associate fellow at Chatham House and a former director of the Pew Research Centre, is that almost none of the brightest brains in the Democratic Party spotted trends that were hiding in plain sight.
“The polling data suggested he was stronger than people gave him credit for. And people underestimated that this was someone who had spent almost his entire life as a salesman,” Stokes tells the Telegraph.
What’s more, adds Stokes, the ructions and dissatisfactions that Trump has seized upon should have been no secret.
“For years now, going back to the 1990s, polling data showed that Americans were increasingly disenchanted with what they saw as the burden of global leadership, military or economic. And the question we would ask at Pew all the time was in essence: do you think we do too much or not enough? And people basically said, ‘We do too much, and the world takes advantage of us.’”
The oral histories (the majority of which were recorded between 2019 and 2023) show the Obama White House was not entirely oblivious to the shifting sentiment in the US – and yet missed the true depth of many voters’ despair and frustration.
In fact, says Charles Kupchan, a foreign affairs expert who advised Obama on national security in the last three years of his presidency: “We were all aware of these issues, all aware of the problem, talked about it regularly, openly”.
But, he adds, the administration “underestimated how much traction these issues got, and the degree to which [now] President Trump would be able to tap into that discontent and communicate to a disaffected segment of the electorate that he had their back and that he was their guy”.
The 2011 White House Correspondents’ Dinner is seen as a landmark moment partly because Obama’s public mockery of Trump now looks like hubris, and partly because a story has grown up that it was his humiliation that evening that drove Trump to seek the White House.
But the seeds of miscomprehension were laid much earlier, argued Richard Trumka, a Democrat-aligned trade unionist who died in 2021.
It was Obama’s decision to bail out the banks following the 2008 financial crisis, he told researchers, that “actually destroyed, in many workers’ minds, the belief that there was somebody out there that was going to fight for them over Wall Street”.
Obama, he said, knew that workers were losing homes and jobs, but just seemed incapable of taking on board the anger that would be felt by many millions.
“It was not that we didn’t have meetings. We had meetings. It’s just that after the meetings were over, not much changed, because the inner circle and the predominant thinking inside the administration was Wall Street-driven,” Trumka said.
At one dinner with critical prominent economists, he added: “The president says, ‘I understand you guys are upset.’ They said, ‘Yes, we’re upset. You’re choosing a path. Instead of restructuring the banks, you’re going to put millions of people out of homes. Yes, we’re upset.’”
Obama, Trumka said, replied: “I understand that, but they give me peace and quiet in the capital market. And I need peace and quiet in the capital market so that I can get this other important work done.”
Trumka never forgot the exchange. “That still rings in my head,” he said. “They [the Obama administration] never understood the anger. Quite frankly, when that [the financial crash and subsequent bailouts] happened, people wanted vengeance.”
That tale of a breakdown of trust between Obama’s White House and the American public, which Trump seized on in his rise to office, comes up in a range of policy areas covered by the oral histories.
Michael Morell, who was a deputy director of the CIA under Obama, describes Edward Snowden’s revelations about data surveillance programs as disastrous for trust in security institutions.
The President may have been confident that the intelligence gathering was constitutional, but “we were all wrong about the public perception of that,” he says.
“It raised questions among Americans about the intelligence community and what it was doing with Americans, not spying on foreigners, but spying on Americans, particularly young people, particularly Silicon Valley.”
Taken together, the picture that emerges from the interviews is one of collapsing popular belief in a system that simply could not, seemingly for its own psychological reasons, grasp what was truly going on.
But that failure to come to terms with the realities of the moment was by no means confined to 1600 Pennsylvania Ave. There were also plenty of high-ranking Republicans who misread the national mood and were blindsided by Trump’s rise.
“I just didn’t think he was going to go the distance. I didn’t think he’d get the nomination [as the Republican candidate for the presidency in 2016]. He did, and so, that was my first taste of just how far the base had moved, and how Trump had really gripped this populism, tapped this vein,” says Paul Ryan, who served as the Republican speaker of the House of Representatives between 2015-2019.
It was only weeks before the 2016 election that Ryan fully realised the changes that were underway.
“I’ve been doing grassroots politics in Wisconsin for 20 years, and almost always I recognise every face in the crowd, because I’ve met everybody,” he says to the researchers, recalling a particular rally from which he had banned Trump following the latter’s notorious comments about grabbing women “by the p**sy”.
“That crowd, I recognised half the people. The other half were people I’ve never seen before, and they were p***ed at me for disinviting Donald Trump, and that’s when it sort of occurred to me like, ‘Wow, there is something happening here.’”
Stokes, who admits to being as surprised as anyone else by Trump’s political ascent, says there is a thread that unites the establishment’s dismissal of him, which runs from Obama through to his Republican rivals.
“The majority [of them] come out of elite backgrounds, went to good universities, but most importantly, they formed their world view at a time when America was primus inter pares, free trade was gospel, and we would lead the world,” he says.
“I know, because I’m part of that generation, and I think there was a divorce between our life experience and the world view we’ve developed, and life experience and the world view of those guys who I went to high school with who went to work in the steel mills, but their life didn’t work out the way they hoped.
“We saw the data, but we didn’t understand what it meant.”
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