Podcast
Surrounded
Hosted by Jubilee Media · EN
Welcome to Surrounded, where one brave person faces twenty five. Every Sunday, dive into bold debates as a single guest takes on twenty five people with opposing views. No echo chambers, just raw, unfiltered conversations that challenge assumptions and spark connection.If you’re hungry for perspective, ready to wrestle with complexity, and believe in the power of debate, you’re in the right place. Subscribe now and join a community built on curiosity, empathy, and conversation that matters.
64episodes
Episodes
Newest firstAll episodes
Is Trump Losing Support For The War? | Surrounded Follow-Up
2d ago00:44:43Summary readyKikoff: 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 corruption within the Trump and Biden administrations, and who Mat sees as the potential political leaders for the 2028 election. Learn more about your ad choices. Visit megaphone.fm/adchoices
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1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded
1w ago01:43:44Summary readyConservative 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
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1 Journalist vs 20 Trump Supporters (ft Glenn Greenwald) | Surrounded
2w ago01:41:43Summary readyIndependent 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
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Naima vs Charlie Kirk, 1 Year Later | Surrounded Follow-Up
3w ago01:21:23Summary readyJohn 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
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1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded
May 1001:34:50Summary readyKikoff: 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 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
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Israeli vs Palestinian: Can They Agree? | Surrounded Follow-up (ft. Rudy Rochman and Dr. Ahmed Soboh)
May 301:04:38Summary readyJohn 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
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1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded
Apr 2601:52:05Summary readyBuild 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 Israel is not committing genocide or apartheid, that anti-Zionism equates to anti-Semitism, that Jews are indigenous to Israel, and that Zionism is a movement of decolonization. As historical trauma meets fierce human rights arguments, can Rochman find a path to mutual understanding with his critics? Learn more about your ad choices. Visit megaphone.fm/adchoices
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Why a Conservative and Liberal Agree on the Epstein Files | Surrounded Follow-Up
Apr 1901:04:06Summary readyJohn 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/adchoices
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1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded
Apr 1201:25:45Summary readyRepresentative Ro Khanna enters the circle to face 20 Americans in a high-stakes debate about power, privilege, and the Epstein files. In this episode of Surrounded, Khanna navigates a deeply polarizing political landscape, defending four uncompromising claims: that America's justice system is two-tiered, the DOJ is illegally withholding crucial files, Commerce Secretary Howard Lutnick must resign, and the U.S. must finally hold its powerful elites accountable. In a space where demands for political transparency clash with fractured public trust, can Khanna find common ground with his critics? Learn more about your ad choices. Visit megaphone.fm/adchoices
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Why Are Vegans So Annoying? | Jack Symes Surrounded Follow-up
Apr 801:08:06Summary readyPhilosopher and author Dr. Jack Symes and John Regalado meet again to dissect Jack's Surrounded debate with 20 meat eaters. In this follow-up, they examine the moral weight of animal suffering, the scientific data behind plant-based longevity, and the controversial argument that modern food systems constitute a global moral crisis. Learn more about your ad choices. Visit megaphone.fm/adchoices
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