1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded

1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded

Conservative commentator Dave Rubin enters the Surrounded circle to confront 20 far-left Democrats in an intense political showdown. In this episode, Rubin navigates a deeply hostile environment, defending four divisive claims: that "wokeism" has caused more damage to America than Donald Trump, that voting for Democrats in 2026 guarantees broken cities, schools, and borders, that progressives push moderate Americans to the right, and that the modern left prioritizes ideology over reality. Can Rubin’s blunt critiques challenge the room's core convictions? Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

1 Journalist vs 20 Trump Supporters (ft Glenn Greenwald) | Surrounded

Independent journalist Glenn Greenwald steps into the circle to confront 20 MAGA supporters in a fiery political showdown. In this episode, Greenwald takes direct aim at the movement's core beliefs with four explosive claims: Trump’s legacy is defined by war rather than peace, his administration bows to the Israel lobby, his presidency was significantly more corrupt than Biden’s, and launching strikes on Iran would be a disaster for the American people. Will his relentless critiques force a reckoning, or can the room defend their champion? Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Naima vs Charlie Kirk, 1 Year Later | Surrounded Follow-Up

John Regalado sits down with recurring Surrounded guest, Naima, to look back at some of her most memorable moments from the Surrounded circle. In this special episode, Naima and John discuss whether Charlie Kirk's assassination changed how she views debate, what it was like to become a political persona overnight, and if she stand by her debate tactics with Charlie Kirk and Ben Shapiro. Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded

Kikoff: Build credit fast and get your first month for just a dollar at getkikoff.com/SURROUNDED [http://getkikoff.com/SURROUNDED] today. Thanks to Kikoff for sponsoring us! Psychiatrist Dr. K sits down with 20 individuals battling depression in a raw and deeply personal conversation about the realities of mental health. In this episode of Surrounded, Dr. K navigates profound emotional divides, defending four core claims: you are overwhelmed rather than broken, hopelessness is a symptom not a final conclusion, deep depression can coexist with productivity and success, and past therapy failures don’t mean you are beyond help. Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Israeli vs Palestinian: Can They Agree? | Surrounded Follow-up (ft. Rudy Rochman and Dr. Ahmed Soboh)

John Regalado is joined by Rudy Rochman and Dr. Ahmed Soboh to revisit their recent Surrounded debate about the Israeli-Palestinian conflict. In this follow-up, they discuss religious extremism on both sides of the conflict, what major compromises both Rudy and Ahmed would consider acceptable in order to achieve peace, and if a one state solution for all could actually be achievable. Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]