Surrounded

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Andrew Yang faces 20 AI optimists in Jubilee’s Surrounded , defending four provocative claims: AI will accelerate inequality, eliminate jobs faster than new ones can emerge, make Universal Basic Income necessary, and push markets to prioritize profit over human dignity. Will Yang’s warnings withstand the optimism—or will the AI believers dismantle his case?

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Austin Julio Broughton steps into the hot seat on Jubilee’s Surrounded to defend four incendiary claims against 20 Liberals: The Left cares more about LGBTQ+ issues than Black Americans. Elective abortion is modern America’s greatest moral failure. Civil rights were won with Bibles and churches, not pronouns and DEI. Republicans care more about free speech than Democrats. Will Austin hold the line...

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Maxwell Frost takes center stage in Jubilee’s Surrounded , facing off against 20 Boomers to defend four hard-hitting claims: Gen Z is the most politically active generation in American history, they aren't too spoiled or lazy, all student debt should be canceled, and while Boomers lived the American Dream, Gen Z can only read about it. Can the youngest member of Congress hold his own against a roo...

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Tim Pool steps into the ring with 20 progressives in this explosive episode of Jubilee’s Surrounded . Standing alone as the sole moderate voice, Pool defends four radical premises: the mainstream left commits more violence than the mainstream right, the Democratic Party has fully embraced authoritarianism, America is actively heading toward a civil war, and the U.S. Constitution effectively no lon...

On this week's episode, Officer Brandon Tatum joins host Parris Rose to recap Tatum's time in the Surrounded Circle. They discuss several clips with the guest debators, and break down some of the most heated moments of the discussion.

Officer Tatum steps into the center of Jubilee’s Surrounded to take on 20 Black Liberals in a high-stakes debate over race, politics, and responsibility. He stands alone to defend four explosive claims: Trump and the GOP are better for the Black community than Democrats, police do more good than harm, Black-on-Black crime is the most critical threat, and systemic racism is used as an excuse to avo...

Mark Manson steps outside the circle to unpack his debate with 20 manosphere creators. Is the manosphere helping men—or trapping them in an echo chamber of insecurity? What We Unpack in This Episode The Looksmaxxing Trap: Why hyper-focusing on superficial traits turns dating into a transaction—and leaves men feeling more isolated than ever. Echo Chambers vs. Reality: How the manosphere monetizes m...

Mark Manson steps into the circle against 20 manosphere creators in Jubilee’s Surrounded, defending four hard-hitting claims: the manosphere is a predatory business profiting off male anger, a woman's body count is irrelevant, porn has ruined men far more than feminism, and true attractiveness stems from respecting women. Will Manson dismantle the echo chamber with reason, or will the pack overrun...

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...

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 skep...

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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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 accountabil...

Kikoff: Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us! 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 corrupti...

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...

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 str...

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...

Kikoff: Build credit fast and get your first month for just a dollar at 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...

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 ab...

Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us! Jewish and Israel rights activist Rudy Rochman rights activist Rudy Rochman faces 20 pro-Palestinian advocates in a deeply emotional and urgent debate over the Israeli-Palestinian conflict. In this episode of Surrounded, Rochman defends four core claims: that...

John Regalado sits down with Andrew (Liberal) and Marien (Conservative) from Ro Khanna’s Epstein Files Surrounded debate to unpack the fallout. They revisit why the Epstein Transparency Act fell short, whether holding the “Epstein class” accountable has become empty political rhetoric, and if Marien’s loyalty to Trump has shifted at all. Learn more about your ad choices. Visit megaphone.fm/adchoic...