Isaiah Martin steps into Surrounded as the lone Democrat facing 20 MAGA Republicans. He challenges four core pillars of Trump’s agenda: that mass deportations make communities less safe, Trump serves the wealthy while leaving everyday Americans behind, DOGE was a complete failure, and Trump’s policies damage the economy. Will his arguments have an impact, or just reveal how wide the divide is?

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John Regalado sits down with Bryan, Anastasia, and Jack to unpack the most revealing moments from their Surrounded debate with Doctor Mike. In this follow-up interview, they dig into the deep mistrust between everyday people and the medical establishment, why skepticism around Big Pharma keeps growing, and how lifestyle, diet, and personal responsibility collide with institutional medicine.

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Ex–mafia boss Michael Franzese steps into the Surrounded circle to face 20 cops in a rare role reversal. He challenges four core assumptions about modern policing: that undercover stings often manufacture crime, that law enforcement justifies breaking the law to catch criminals, that success is measured by arrests instead of safer streets, and that paid informants are deeply unreliable. Will his insider perspective expose uncomfortable truths—or be shut down by those sworn to uphold the law?

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Adam Mockler joins John Regalado to revisit the most charged moments from his Surrounded debate with 20 conservative college students. In this follow-up, Adam unpacks the rise of political extremism among young voters, how inflammatory rhetoric becomes normalized from the top down, why Trump’s “golden age” economy doesn’t hold up under scrutiny,  and what real political courage might look like in 2026.

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It’s one liberal college dropout against 20 conservative college students. Adam Mockler steps into the Surrounded circle to defend four provocative claims: Trump is fueling a rise in fascism among young people, the economy is not in a so-called “golden age,” children are safer with the average undocumented immigrant than with Donald Trump, and Trump is the most corrupt president in U.S. history. Can one outsider hold his ground against a room full of undergrads?

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John Regalado sits down with Tyler, Jenny and Nick – participants from the Surrounded episode featuring Piers Morgan – to unpack the moments that sparked the most friction in their debate. In this follow-up, they dig deeper into their conversations around free speech absolutism, whether “wokeness” is truly authoritarian, the limits of cancel culture, and how media incentives and culture wars crowd out material issues like wages, housing, and healthcare.

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Tim Miller joins John Regalado to revisit some of the most thought-provoking moments from his Surrounded debate with 20 Gen Z conservatives. In this follow-up interview, Tim and John explore generational shifts on the right, how extreme immigration tactics and ICE enforcement become normalized, the moral tradeoffs of the Second Amendment, and even reflect on the famous Mehdi Hasan debate.

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Texas State Rep. James Talarico joins Surrounded to face 20 undecided Texas voters in a conversation about policy, power, and what’s at stake in 2026. He argues that cuts to healthcare and food assistance hurt everyone, that immigrants make America stronger and more prosperous, that every vote will matter next cycle, and that the real divide in politics isn’t left vs. right but top vs. bottom. Will his message resonate with voters still on the fence?

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Doctor Mike sits down with 20 RFK Jr. supporters in a heated debate over trust, science, and the future of public health. He argues that RFK Jr. is harming the nation’s wellbeing and should step down as HHS Secretary, that the MAHA movement is undermining the doctor–patient relationship, that Big Pharma is far more trustworthy than Big Supplement, and that MAHA’s leaders are driven by power and politics—not health. Can medical expertise cut through the skepticism?

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Piers Morgan steps into Surrounded to face 20 “woke liberals” in a charged cultural showdown. He defends four blunt claims: masculinity has never been toxic, woke ideology is anti-liberal and veers toward the fascistic, gender-neutral pronouns serve no purpose, and cancel culture poses a real threat to free speech. What happens when one outspoken critic meets a room full of his biggest challengers?

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