Obama's Team Underestimated Trump's Political Resilience

New oral history reveals how the Obama administration dismissed Trump's chances of winning the presidency.

Published on Feb. 20, 2026

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A new oral history of the Obama presidency reveals how the president's advisers were repeatedly surprised by Donald Trump's political resilience, even as they mocked and dismissed him. The interviews show that Obama's team failed to anticipate Trump's ability to connect with an electorate increasingly distrustful of government and establishment figures, ultimately leading to his unexpected victory in the 2016 election.

Why it matters

The Obama administration's blindspot regarding Trump's political appeal highlights the challenges facing established political figures in understanding and connecting with a changing electorate. The interviews provide insight into how the political and media elite can sometimes misread the public mood, with significant consequences.

The details

The oral history, which includes interviews with over 450 people, shows that Obama's advisers were repeatedly caught off guard by Trump's ability to withstand mockery and scandals that they believed would end his political ambitions. They described a 'learning curve' on how Americans, both young and old, were getting their news and the rise of 'team' politics. Despite Trump's controversial rhetoric and actions, the White House failed to anticipate his political resilience and connection with voters distrustful of government.

  • In October 2016, five weeks before Election Day, Obama's political director David Simas told the president that Trump was 'done'.
  • On the night before the 2016 election, Simas recognized that Clinton's lead had shrunk to just 3 points, but still believed she would win.

The players

Barack Obama

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

Donald Trump

The 45th President of the United States, who defeated Hillary Clinton in the 2016 election despite being dismissed by the Obama administration.

David Simas

Obama's White House political director, who wrongly believed Trump had no chance of winning the 2016 election.

Josh Earnest

Obama's former White House press secretary, who said it was 'hard not to take it personally' when Trump won the election.

David Axelrod

Obama's former senior adviser, who acknowledged that the administration 'misread' Trump's political appeal.

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What they’re saying

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

— Josh Earnest, Former White House Press Secretary (Obama Presidency Oral History)

“Obviously, we misread that.”

— David Axelrod, Former Senior Adviser to President Obama (Obama Presidency Oral History)

What’s next

The oral history project is expected to provide further insights into the Obama administration's perspective on the rise of Donald Trump and the 2016 election.

The takeaway

The Obama team's failure to anticipate Trump's political resilience and connection with disaffected voters highlights the challenges facing established political figures in understanding and responding to a rapidly changing electorate influenced by social media and shifting news consumption patterns.