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

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: Emmy-winning actress Drea de Matteo joins Will to talk about her career, the state of Hollywood, and why she’s charting her own path in an industry that feels more broken than ever. From The Sopranos to today, Drea opens up about fame, resilience, and reinvention. Subscribe to 'Will Cain Country' on YouTube here: Watch Will Cain Country! Follow Will on X: @WillCain Learn more about your ad choices. Visit podcastchoices.com/adchoices