Obama's Team Underestimated Trump's Political Resilience

New oral history reveals how Obama's advisers were blindsided by Trump's rise to power

Published on Feb. 20, 2026

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A new oral history of the Obama presidency reveals how the former president's team was repeatedly surprised by Donald Trump's political resilience, even as they mocked and dismissed him. The interviews show that Obama's advisers, including top officials like political director David Simas, failed to anticipate Trump's ability to connect with alienated voters, despite the administration's accomplishments like the economic recovery and healthcare reform.

Why it matters

The interviews provide insight into how the political establishment, including the highly experienced Obama team, misjudged the public's growing distrust of government and openness to an outsider candidate like Trump. This blind spot had major consequences, contributing to the shock of Trump's 2016 victory over Hillary Clinton.

The details

The oral history, which includes interviews with 450 people, shows that Obama's team was repeatedly caught off guard by Trump's staying power, even as they tried to dismiss him as a 'clown.' White House political director David Simas told Obama just weeks before the 2016 election that Trump had no chance of winning, only to see Clinton's lead shrink on Election Day. Speechwriter Jon Favreau said he never even briefly considered the possibility of Trump becoming president. The interviews also reveal how the Obama team struggled to adapt to the growing influence of social media and conspiracy theories that helped fuel Trump's rise.

  • In April 2011, Trump fueled the false conspiracy theory that Obama was not born in the United States.
  • On April 27, 2011, Obama released his long-form birth certificate to address the issue.
  • A few days later, at the White House Correspondents' Dinner, Obama mocked Trump in his speech, which speechwriter Jon Favreau said was 'cathartic' for the president.
  • The next day, Obama announced the killing of Osama bin Laden during a U.S. commando raid in Pakistan.

The players

Barack Obama

The 44th President of the United States, who served two terms from 2009 to 2017.

David Simas

Obama's White House political director, who incorrectly told the president that Trump had no chance of winning the 2016 election.

Jon Favreau

Obama's speechwriter, who said he never even briefly considered the possibility of Trump becoming president.

David Axelrod

Obama's senior adviser, who initially advised the president to ignore Trump's false claims about Obama's birthplace.

Nancy-Ann DeParle

A former White House deputy chief of staff for policy, who thought Obama's decision to release his birth certificate was a mistake.

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What they’re saying

“He's done.”

— David Simas, White House political director (ksgf.com)

“Not many people even expected that he had a chance to win. 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.”

— Josh Earnest, Former White House press secretary (ksgf.com)

“I thought what he was doing was racist. I thought that it was not just damaging to Obama but damaging to the country.”

— Jon Favreau, Speechwriter (ksgf.com)

What’s next

The Obama Presidency Oral History project plans to release additional interviews in the coming months, providing further insights into the administration's perspectives on the rise of Donald Trump.

The takeaway

The Obama team's failure to anticipate Trump's political resilience and connection with disaffected voters highlights the blind spots of the political establishment, even among experienced and accomplished officials. This episode underscores the need for greater understanding of the changing dynamics of American politics and the growing influence of social media and alternative narratives.