John Regalado sits down with non-voter Carlheb to unpack their recent Surrounded debate with Wes Moore. In this follow-up, they discuss the moral tension that comes with participating in an imperfect and often corrupt system, the legacy of slavery in the current political consciousness, the influence of black revolutionaries like Fred Hampton, and whether or not Wes Moore convince Carlheb to cast his vote in future elections.

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Democratic leader Wes Moore faces 20 non-voters in a compelling episode of Surrounded, tackling political disillusionment head-on. He challenges the room with three urgent claims: 1) nothing shapes policy more effectively than your vote, 2) bad politics thrive when citizens don’t participate, and 3) abstaining from the ballot protects corruption rather than protesting it. Can Moore convince a skeptical crowd to reclaim their civic power, or will their disillusionment prove too deep to overcome?

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John Regalado sits down with Lori and Julia Kate to unpack their viral Surrounded debate with Dean Withers. In this follow-up, they dive deeper into their personal backgrounds and values, their perspectives on Donald Trump, and discuss the discourse of modern political commentary.

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Kyla Turner steps outside the circle to join John Regalado in this follow-up to the viral Dave Rubin Surrounded debate. In this discussion, Kyla shares her perspective on the debate – covering the perceived contradictions of Rubin's political alignment and identity, political extremism in American politics, economic metrics under the Trump administration and the necessity for political accountability and effective governance across the political spectrum.

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John Regalado sits down with Mat Nuclear to unpack his recent Surrounded debate with Glenn Greenwald. In this follow-up interview, John and Mat discuss the growing public sentiment against the United States' involvement in Iran, allegations of corruption within the Trump and Biden administrations, and who Mat sees as the potential political leaders for the 2028 election.

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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?

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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?

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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.

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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.

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