Jubilee Media

Surrounded

Society EN ↓ 68 episodes

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.

Author

Jubilee Media

Category

Society

Latest episode

Jul 5, 2026

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Episodes

Cenk Uygur vs 20 Democrats & Republicans 03.08.2025

Cenk Uygur, a prominent populist voice, engages in a compelling debate with 25 Democrats and Republicans. He presents four thought-provoking claims: Democrats and Republicans find common ground on economic issues while using culture wars as a diversion, the Democratic agenda is more about marketing than genuine mission, the Republican party primarily serves the wealthy, and political power is ulti...

Can 1 Cop Defend Himself Against 20 Criminals? | Surrounded 26.07.2025

Officer Kevin Donaldson faces 20 individuals with criminal records to discuss and defend four critical claims: that police use lethal force only as a last resort, most officers are selfless and honorable, racial profiling of Black and Brown people is not a widespread issue, and that police officers are often judged too harshly. Can the cop find common ground, or will his perspectives be challenged...

Mehdi Hasan vs 20 Far Right Republicans 20.07.2025

Progressive heavyweight Mehdi Hasan faces off against 20 Far-Right Republicans in one of the most intense episodes of Surrounded yet. He arrives armed with four bold claims: Donald Trump is pro-crime, he is defying the Constitution, immigrants are good for America, and Trump’s Gaza plan amounts to ethnic cleansing. Will he change any minds, or will the far-right conservative wall hold strong? Lear...

Charlie Kirk vs 20 Liberal College Students 13.07.2025

Charlie Kirk steps into Jubilee's Surrounded, a lone conservative against 20 woke college students, defending four claims: abortion is murder, college is a scam, trans women are not women, and Kamala Harris is a DEI candidate. Will Kirk persuade the masses or be drowned out by the dissent? Learn more about your ad choices. Visit megaphone.fm/adchoices

Is Candace Owens Living the Feminist Dream? | Surrounded Follow-Up 06.07.2025

John Regalado sits down with Candace Owens, to revisit the most heated moments of her Surrounded debate with 20 feminists. In their conversation Candace reflects on being labeled a feminist, her influence on culture, motherhood, the impact of Sex and the City, and her opinions on women's voting rights. Follow our Youtube channel:https://www.youtube.com/@jubilee Follow Candace:https://www.instagram...

Destiny vs 25 Donald Trump Voters 03.07.2025

In this Throwback Thursday episode of Surrounded, streamer and political commentator Destiny goes head-to-head with 25 Trump supporters. He defends four bold claims: Donald Trump is unfit for the presidency, Kamala Harris has the better immigration plan, Trump’s border policies will fuel inflation and tank the economy, and Donald Trump is a fascist. Revisit the debate and decide whether Destiny he...

Candace Owens vs. 20 Feminists 29.06.2025

In this episode of Surrounded, Candace Owens goes head-to-head with 20 feminists to defend four controversial claims: the sexual revolution devalued women, raising children is more fulfilling than any career, we live in a matriarchy, and feminism has made life easier for men. Will Owens sway the room or be overwhelmed by the opposition? Learn more about your ad choices. Visit megaphone.fm/adchoice...

20 Trump Supporters Take on 1 Progressive (feat. Sam Seder) 22.06.2025

Sam Seder stands alone against 20 Trump supporters, armed with four claims: Trump’s DEI attacks mask a corporate power grab, voting for Trump was a mistake unless you’re a billionaire, the GOP will gut Social Security and healthcare, and Trump’s policies only enrich the elite. Will his arguments cut through, or will MAGA loyalty shut him down? Learn more about your ad choices. Visit megaphone.fm/a...

Doctor Mike vs 20 Anti-Vaxxers 17.06.2025

In this high-stakes episode of Surrounded, Doctor Mike takes on 20 anti-vaxxers with four sharp claims: anti-vaccine lies cost lives, vaccine immunity beats natural immunity, RFK Jr. is a public health menace, and anti-vaxxers are both victims and villains of misinformation. Can science silence skepticism or will dissent hold firm? The debate starts now. Learn more about your ad choices. Visit meg...

A Palestinian Who Doesn’t Agree With Protestors | Ahmed Fouad Alkhatib Surrounded Follow-Up 15.06.2025

John Regalado sits down with Ahmed Fouad Alkhatib, to revisit the most heated moments of his Surrounded debate with 20 Pro-Palestine protesters. They discuss his experience being at the centre of the Surrounded format, some of the most polarizing aspects of the pro-Palestine movement, and the difficulty of threading the path between both sides. Follow our YouTube channel: https://www.youtube.com/@...

20 Pro-Palestine Protestors vs Ahmed Fouad Alkhatib 08.06.2025

Ahmed Alkhatib steps into the circle, challenging 20 Pro-Palestine protestors with four divisive claims: October 7th was a disaster that opened the worst chapter in Palestinian history, armed resistance will get Palestinians nowhere, angry protests in the West are not helpful, and being pro-Palestine necessitates accepting a free Palestine side by side next to Israel. Will his arguments hold, or w...

Is Jordan Peterson Actually a Christian? | Surrounded Follow Up 01.06.2025

John Regalado sits down with Cade, Zina and Danny, to revisit the most heated moments of their Surrounded debate with Jordan Peterson. They discuss their debate tactics as well as their personal backstories as atheists. Follow our YouTube channel:https://www.youtube.com/@jubilee Follow Cade:youtube.com/@GayExTradFollow Zina:tiktok.com/@zinaaweenaaFollow Danny:youtube.com/@DannyPhilTalk Follow John...

1 Atheist vs 25 Christians (feat. Alex O'Connor) 29.05.2025

Alex O'Connor steps into Jubilee's Surrounded, challenging 25 Christians with four seismic claims: suffering shatters God's likelihood, the Bible commands genocide, the resurrection lacks evidence, and Jesus never claimed divinity. Will his arguments hold, or will faith prevail? Follow our YouTube channel: https://www.youtube.com/@jubilee Follow Alex O'Connor:https://www.youtube.com/cosmicskeptic...

Jordan Peterson vs 20 Atheists 25.05.2025

Jordan Peterson faces 20 atheists in Jubilee's Surrounded, defending four controversial claims: atheists reject God without understanding what they're rejecting, science can't provide morality or purpose, everyone worships something whether they know it or not, and atheists steal Christian values while denying Christianity's foundation. Will Peterson convert the non-believers or get crushed by the...

Why It Always Comes Back to Butt Stuff | We Followed Up With Zander Moricz 18.05.2025

John Regalado sits down with Zander Moricz, to revisit the most heated moments of his surrounded debate. They discuss Trans Youth, misinformation, and the future of LGBTQ+ politics. Follow our YouTube channel: https://www.youtube.com/@jubilee Follow Zander Moricz & SEE Alliance: https://www.instagram.com/zandermoricz https://seeourpower.org https://x.com/zandermoricz Follow John Regalado: https://...

1 Sports Analyst vs 25 NBA/NFL Fans (ft. Skip Bayless) 11.05.2025

Skip Bayless faces 25 NBA and NFL fans in Jubilee’s Surrounded, defending four bold takes: Magic Johnson is the greatest Laker, Jordan is laughably better than LeBron, Mahomes is overrated, and Brady made Belichick. Will Skip stand his ground or get shut down? Follow our YouTube channel: https://www.youtube.com/@jubilee Follow Skip Bayless: https://www.instagram.com/skipbayless https://www.youtube...

1 LGBTQ+ Activist vs 25 Conservatives (ft. Zander Moricz) 11.05.2025

One LGBTQ+ activist is surrounded by twenty-five conservatives in a raw conversation about identity, power, and the future of America’s youth. Zander Moricz steps into the circle to challenge assumptions and open a dialogue. From banned books to drag queens, healthcare to political power, this conversation asks: What are we really protecting, and at what cost? Follow our YouTube channel: ⁠https://...

Surrounded Podcast | Show Trailer 30.04.2025

When one brave soul enters a room full of disagreers, what human interactions will follow? From Jubilee Media, this is the Surrounded podcast. Join John Regalado every week for audio versions of the main episodes, as well as exclusive follow-up interviews with cast members, where we dig deeper into the disagreements that happen on the show. Learn more about your ad choices. Visit megaphone.fm/adch...

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