Chicago Rejects Trump’s Help As 54 Shot Over Weekend (ft. Drea de Matteo)

Will Cain Country · Sep 2, 2025 · 1h 21m

Story #1: In 'Quick Takes,' Will hits on the big stories of the week: Chicago Mayor Brandon Johnson and Gov. JB Pritzker (D-IL) worry about President Donald Trump's help on crime as 54 people are shot in Chicago over the weekend, and Patrick Bet-David confronts socialists in online debate while the 'New York Times' denies Zohran Mamdani's socialism

Story #2: 'Off The Weekend' takes you behind the curtain of two big interviews: Vice President J.D. Vance and Barstool’s Dave Portnoy. Will shares what you didn’t see on-air, the questions that hit hardest, and answers your questions.

Story #3…