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Surrounded

Surrounded

Jubilee Media 63 Episodes Jun 28, 2026

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.

Episodes

Is Dean Alpha or Beta? | Surrounded Follow-Up Jun 28, 2026 4083 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
Dean Withers vs 20 MAGA Women | Surrounded Jun 21, 2026 7055 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:   / lov
Is Dave Rubin Living in Reality? Surrounded Follow-Up Jun 14, 2026 2743 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
Is Trump Losing Support For The War? | Surrounded Follow-Up Jun 7, 2026 2683 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 corruptio
1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded May 31, 2026 6224 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
1 Journalist vs 20 Trump Supporters (ft Glenn Greenwald) | Surrounded May 24, 2026 6103 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
Naima vs Charlie Kirk, 1 Year Later | Surrounded Follow-Up May 17, 2026 4883 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
1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded May 10, 2026 5690 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 o
Israeli vs Palestinian: Can They Agree? | Surrounded Follow-up (ft. Rudy Rochman and Dr. Ahmed Soboh) May 3, 2026 3878 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
1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded Apr 26, 2026 6725 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: th
Why a Conservative and Liberal Agree on the Epstein Files | Surrounded Follow-Up Apr 19, 2026 3846 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
1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded Apr 12, 2026 5145 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

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