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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.
25 Episodes
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In this episode of Surrounded, Lila Rose, a staunch pro-life advocate, debates 25 pro-choice advocates. She presents and defends four controversial claims: that abortion causes lasting harm to women, is never morally justified, that every unborn child has a right to life, and that abortion is unconstitutional and should be banned. Will her perspective hold up under pressure, or be challenged into reconsideration?
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1Dean Withers enters Jubilee’s Surrounded as the lone liberal facing 20 Trump voters. He defends four fiery claims: Donald Trump is a racist, Trump doesn’t care about the American people, Kamala Harris would make a better president, and conservatives don’t actually care about family values. Will Dean hold his ground or be overrun by the conservative crowd?
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John Regalado sits down with Mason, Gabby, James and Isabella to revisit their Surrounded debate with Patrick Bet-David. They share their experiences that led them to becoming anti-capitalist and discuss taxing the ultra-rich, enduring poverty, reimagining socialism and the potentially life-changing offers that Patrick put on the table during the episode.
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Patrick Bet-David, entrepreneur and outspoken capitalist, takes the hot seat in Jubilee’s Surrounded, facing 20 anti-capitalists. He argues four bold claims: incentive drives capitalism, capitalism has lifted more people out of poverty than any other system, equal wealth distribution would collapse within five years, and the U.S. is already more socialist than capitalist. Will Patrick defend his vision, or get dismantled by the opposition?
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Amanda Seales joins John Regalado to revisit the most memorable moments from her Surrounded debate with 20 black conservatives. In this follow up interview, Amanda discusses the necessity of reparations, the problems with policing, and why she believes Socialism is an alternative to capitalism that would better serve Black Americans.
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Amanda Seales, outspoken comedian and cultural critic, faces 25 Black conservatives in Jubilee’s Surrounded. She stands by four uncompromising claims: reparations are both just and necessary, “Black-on-Black crime” is fueled by underinvestment and over-policing, systemic racism is a lived reality grounded in history and data, and Black conservatism fails the working class. Will her arguments be enough to sway the room?
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Cenk Uygur joins John Regalado to unpack the most revealing moments from his Surrounded debate with a room full of Republicans and Democrats. From calling out identity politics to exposing how both parties bow to their donors, Cenk lays out why he believes the entire political system is rigged and what real populism actually looks like.
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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 ultimately controlled by media and money. Will Cenk's arguments resonate, or will he face an uphill battle against the bipartisan consensus?
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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 by the experiences of the group?
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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?
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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?
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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.
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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 held his own against the MAGA faithful.
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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?
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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?
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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.
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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.
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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 will the group shut him down?
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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.
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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?
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PBD is awful. If you ever listened to his pod he never answers anything. "Let me answer your question with a question....."
Great format and most have been brilliant and respectful with the exception of Amanda Seales, she just roared and shouted down those who she struggled with. Maybe try have someone keep it as a debate, it ruined it.
I really appreciate the information you shared. It's well-explained and very helpful. Keep it up the great work! 👍 Looking forward to more valuable insights from you. 😊 https://minecrftipa.com/
I agree. We can only move forward if we work together.