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Why the Obama Administration Never Saw Trump Coming

Donald Trump first toyed with the idea of running for President in the 1988 election, but he didn't go through with it. He ran in 2000 under the Reform Party, then floated the idea again in 2012. So when he ran in 2016, it was natural for the incumbent Obama administration—like many of us—to brush it off as a joke. With a decade of hindsight, it's obvious that we and the Obama administration were sorely mistaken. With two election wins under his belt and a powerful second term in action, Trump has been an unmistakeable force in U.S. politics for a decade now. How did we all miss the signs? That question emerged again and again in a new series of interviews archived in the Obama Presidency Oral History from Columbia University. In conversations recorded between 2019 and 2023, strategists like David Axelrod, speechwriters like Jon Favreau and administration officials like press secretary Josh Earnest all mused aloud to their interviewers about the shock of the Trump win and the color it put on their legacy. Michael Smerconish and producer TC Cannon discuss the archive and reflect on how Trump shocked the world with his first win. Vote on today's poll and subscribe to the daily newsletter at www.smerconish.com