July 27, 2026 - Kaitlan Collins

Jon Stewart breaks down the rescheduled White House Correspondents’ Dinner, after the original event was derailed by an attempted shooting. Trump’s defiant return to the stage featured timely 2016 references, wordy roasts that missed the mark, and trailing explanations of jokes that bombed. Jon gives the speech a Comedy 101 critique and wonders which correspondents’ dinner ended more unceremoniously. He also sits down with CNN’s award-winning chief White House correspondent and “The Source” anchor Kaitlan Collins to discuss the dinner, how she handles insults from the president, how the press corps has changed over 10 years of covering Trump, reporters’ frustration with his refusal to answer questions, and the value of follow-ups. Plus, Jon prepares a little roleplay to encourage Collins to give Trump a taste of his own medicine.