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Surrounded

Surrounded

Jubilee Media 63 Episodes Aug 19, 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

Tim Pool vs Progressives | Surrounded Follow-Up
Tim Pool vs Progressives | Surrounded Follow-Up Aug 19, 2026 00:56:28 Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-videoLET’S BE FRIENDSInstagram: https://www.instagram.com/jubileemedia/TikTok: https://www.tiktok.com/@jubilee?lang=enWebsite: https://www.jubileemedia.comOUR LOVE + DATING CHANNEL 🍑YouTube: https://www.youtube.com/@lovecommanectarInstagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nec
1 Moderate vs 20 Progressives (ft. Tim Pool)
1 Moderate vs 20 Progressives (ft. Tim Pool) Aug 16, 2026 01:40:32 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 long
Is Trump Better for Black Americans Than Democrats? | Surrounded Follow-Up w/ Officer Tatum
Is Trump Better for Black Americans Than Democrats? | Surrounded Follow-Up w/ Officer Tatum Aug 9, 2026 01:02:20 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.
1 Black Conservative vs 20 Black Liberals (ft. Officer Tatum)
1 Black Conservative vs 20 Black Liberals (ft. Officer Tatum) Aug 2, 2026 01:59:47 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
What Has The Manosphere Taught Us? | Surrounded Follow-Up
What Has The Manosphere Taught Us? | Surrounded Follow-Up Jul 27, 2026 00:50:23 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 m
1 Anti-Manosphere vs 20 Manosphere (ft. Mark Manson) | Surrounded
1 Anti-Manosphere vs 20 Manosphere (ft. Mark Manson) | Surrounded Jul 27, 2026 01:24:29 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
How Can You Care But Not Vote? | Surrounded Follow-Up
How Can You Care But Not Vote? | Surrounded Follow-Up Jul 12, 2026 01:03:31 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
Governor Wes Moore vs 20 Non-Voters | Surrounded
Governor Wes Moore vs 20 Non-Voters | Surrounded Jul 5, 2026 01:21:47 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
Is Dean Alpha or Beta? | Surrounded Follow-Up
Is Dean Alpha or Beta? | Surrounded Follow-Up Jun 28, 2026 01:04:33 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.
Dean Withers vs 20 MAGA Women | Surrounded
Dean Withers vs 20 MAGA Women | Surrounded Jun 21, 2026 01:53:05 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:   / lovecom
Is Dave Rubin Living in Reality? Surrounded Follow-Up
Is Dave Rubin Living in Reality? Surrounded Follow-Up Jun 14, 2026 00:42:13 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
Is Trump Losing Support For The War? | Surrounded Follow-Up Jun 7, 2026 00:41:13 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

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