Surrounded

Jubilee Media

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.

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34 episodes
weekly
Avg 1 hr 19 min
English

Episodes 34

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June 28 · 1 hr 4 min
Is Dean Alpha or Beta? | Surrounded Follow-Up
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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June 21 · 1 hr 53 min
Dean Withers vs 20 MAGA Women | Surrounded
APPLY TO BE ON SURROUNDED: https://bit.ly/43MF3yZ Open General Casting Application: https://bit.ly/4xCliYn Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: / jubileemedia TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: / @lovecommanectar Instagram: / lovecommanectar Nectar app: https://lovecommanectar.co/m/download... ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com FEATURING Dean: / itsdeaann Tracey: / spartra Enya: / enyaschutsky Georgia: / georgiagchapa Gina: instagram.com/ginasbeverlyhills Shannon: / shannonseverywhere Aniela: / aniela.luluuuu Maricarmen: / maricarmensainzchapa Tish: / tishis_awinner Emilie: / enaples.in.naples Ashley: / ashley__kenya Kytia: / kytialamour Lori: https://x.com/LoriMills4CA42 Justine: / juicetinee_a Zuriel: / bal_zur Annette: / annettedjackson Leia: / leialiftz Shiva: / shivaforfreedom Julia: / juliakateofficial
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June 14 · 42 min
Is Dave Rubin Living in Reality? Surrounded Follow-Up
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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June 7 · 41 min
Is Trump Losing Support For The War? | Surrounded Follow-Up
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 corruption within the Trump and Biden administrations, and who Mat sees as the potential political leaders for the 2028 election.
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May 31 · 1 hr 40 min
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?
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May 24 · 1 hr 38 min
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?
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May 17 · 1 hr 17 min
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.
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May 10 · 1 hr 31 min
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 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.
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May 3 · 1 hr 1 min
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.
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April 26 · 1 hr 48 min
1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded
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 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?
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April 19 · 1 hr
Why a Conservative and Liberal Agree on the Epstein Files | Surrounded Follow-Up
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.
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April 12 · 1 hr 22 min
1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded
Representative 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?
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April 8 · 1 hr 4 min
Why Are Vegans So Annoying? | Jack Symes Surrounded Follow-up
Philosopher 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.
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April 5 · 1 hr 38 min
1 Vegan vs 20 Meat Eaters (ft. Jack Symes)
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Vegan advocate Jack Symes enters the circle to face 20 meat-eaters in an intense debate about the ethics of our diets. In this episode of Surrounded, Symes navigates a deeply polarizing landscape, defending four uncompromising claims: that extreme suffering for trivial pleasure is morally indefensible, that everyone should aim to be vegan, that factory farming ranks among the worst atrocities in history, and that veganism is fundamentally good for the world and humanity. In a space where personal lifestyle clashes with moral obligation, can Jack’s perspective find common ground with his critics, or are the divides too deep to bridge?
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Showing 21–34 of 34 episodes