Investigative Reporting

How Obama’s Administration Failed to See the Trump Surge Coming

By National Security Desk | February 18, 2026

Despite relentless mockery and dismissal, Obama’s top aides failed to grasp Donald Trump’s political resilience, revealing a critical disconnect that reshaped America’s political landscape.

For eight years, President Barack Obama’s administration watched in disbelief as Donald Trump — dismissed repeatedly as a "clown" — refused to fade from the national stage. This glaring blind spot exposed deep flaws within the Washington establishment: an inability to understand America’s growing distrust of government and a failure to recognize the rising power of social media-driven populism. Why Did Obama’s Team Underestimate Trump’s Strength? Interviews with hundreds of former Obama aides reveal a pattern of underestimation and denial. From dismissing Trump's candidacy as laughable to failing to anticipate his eventual Electoral College triumph in 2016, these officials clung...

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