Trump Was Totally Misjudged

Did you see the "Trump Train" coming? Michael didn’t — and neither did Barack Obama’s inner circle. Drawing from newly released oral history interviews on the Obama presidency, Michael explores how top advisers like David Axelrod, Jen Psaki, and Jon Favreau underestimated Donald Trump’s political rise. From the 2011 White House Correspondents’ Dinner roast to the escalator announcement in 2015, this episode revisits the moments many dismissed — and asks why so many got it wrong. Plus, SiriusXM’s Steve Scully joins the conversation with a behind-the-scenes account of that infamous Correspondents’ Dinner — including what was happening off-camera as Trump reacted in real time. Could it all....happen again? Listen in, then rate, review, and share this podcast! Original air date 26 February 2026.