Jubilee Media

Surrounded

Society EN ↓ 87 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

Nov 4, 2026

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Episodes

Doctor Mike vs 20 RFK Jr. Supporters 07.12.2025

Doctor Mike sits down with 20 RFK Jr. supporters in a heated debate over trust, science, and the future of public health. He argues that RFK Jr. is harming the nation’s wellbeing and should step down as HHS Secretary, that the MAHA movement is undermining the doctor–patient relationship, that Big Pharma is far more trustworthy than Big Supplement, and that MAHA’s leaders are driven by power and po...

Piers Morgan vs 20 Woke Liberals 30.11.2025

Piers Morgan steps into Surrounded to face 20 “woke liberals” in a charged cultural showdown. He defends four blunt claims: masculinity has never been toxic, woke ideology is anti-liberal and veers toward the fascistic, gender-neutral pronouns serve no purpose, and cancel culture poses a real threat to free speech. What happens when one outspoken critic meets a room full of his biggest challengers...

Tim Miller vs 20 Gen Z Conservatives 26.11.2025

Tim Miller, a former Republican strategist turned Democrat, faces 20 Gen Z conservatives in a tense generational face-off. He argues that ICE has become a fascist institution, that gun rights aren’t worth the lives lost, that the Trump administration undermines American values, and that red states are run worse than blue ones. Can his insider perspective bridge the divide—or deepen it? Learn more...

Is Bryan Johnson's Immortality a Hoax? | Surrounded Follow-Up w/ Chelsea Gods & Bryton Snyder 23.11.2025

John Regalado sits down with Chelsea Gods and Bryton Snyder to dive deeper into some of the most thought-provoking moments from their Surrounded debate with Bryan Johnson. In this follow up interview, Chelsea and Bryton discuss their criticisms of Bryan's "Don't Die" philosophy, the value of a confrontational approach to debate, and their own perspectives on life, religion and spirituality. Learn...

Bryan Johnson vs 20 Skeptics 16.11.2025

Bryan Johnson, tech entrepreneur and founder of the “Don’t Die” movement, faces 20 skeptics in a provocative debate on life, death, and human potential. Guided by his mission to wage a 'war' with death and its causes, Johnson argues that ending death should be humanity’s top goal, that we may be the first generation to achieve it, that fast food should never be eaten, and that sleep is life’s high...

1 Politician vs 25 Undecided Voters (Feat. Pete Buttigieg) | Surrounded Rewind 09.11.2025

Pete Buttigieg sat down with 25 undecided voters for a Surrounded debate before the 2024 US Presidential Election. He laid out four core arguments: Donald Trump is running for himself while Kamala Harris is running to improve people’s lives, the economy would be stronger under Harris, Americans would gain more rights and freedoms with a Harris–Walz administration, and crime would continue to fall...

What's the Future of The Democrats' Platform? | Surrounded Follow-Up w/ Luke Beasley 02.11.2025

Luke Beasley joins John Regalado to unpack some of the most important talking points from his Surrounded debate with 20 MAGA Boomers. In this follow up interview, Luke and John discuss whether political extremism is more concentrated on the left or the right, which party is better with the economy, the future of the Democratic Party and whether Luke himself would enter politics. Learn more about y...

20 Boomer Trump Supporters vs 1 GenZ Liberal (ft. Luke Beasley) | Surrounded 26.10.2025

Luke Beasley, a Gen Z liberal commentator, faces 25 boomer Trump supporters in a generational clash of politics and perspective. He argues that MAGAnomics hurts the economy, Trump threatens democracy, his supporters lack true patriotism, and Kamala Harris would have made a better president. Can one Gen Z voice cut through decades of conviction? Learn more about your ad choices. Visit megaphone.fm/...

Is There Only One Way to Read the Bible? | Surrounded Follow-Up w/ Allie Beth Stuckey 19.10.2025

Allie Beth Stuckey sits down with John Regalado to revisit some of the most thought-provoking moments from her Surrounded debate with 20 liberal Christians. In this follow up interview, Allie and John discuss homosexuality and whether or not the Bible approves of it, abortion, polarization in our political culture, and the assassination of Charlie Kirk. Learn more about your ad choices. Visit mega...

Allie Beth Stuckey vs 25 Liberal Christians 12.10.2025

Allie Beth Stuckey, a conservative Christian commentator, faces 25 liberal Christians in a charged debate on faith and ideology. She defends four provocative claims: marriage is between one man and one woman, abortion is a grave moral evil, empathy can become sinful, and progressivism clashes with Christianity. Can conviction hold its ground against compassion? Learn more about your ad choices. Vi...

Are We Really Going To End All Abortions? | Surrounded Follow-Up w/ Lila Rose 05.10.2025

Lila Rose joins John Regalado to look back at some of the most heated and interesting interactions from her Surrounded debate with 20 pro-choice activists. In this follow up interview, Lila and John discuss the Catholic approach to sex and reproduction, whether or not life begins at conception, and her controversial vision of a world without abortions. Learn more about your ad choices. Visit megap...

Andrew Callaghan vs 20 Conspiracy Theorists 28.09.2025

Journalist Andrew Callaghan sits down with 20 conspiracy theorists to debate four hot-button claims: QAnon has no basis in fact, 9/11 was carried out by Al-Qaeda, Hunter Biden’s laptop doesn’t prove corruption, and the earth is round. What happens when one journalist goes head-to-head with a room full of skeptics? Learn more about your ad choices. Visit megaphone.fm/adchoices

Lila Rose vs 25 Pro-Abortion Activists 21.09.2025

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...

Dean Withers vs 20 Trump Supporters 14.09.2025

Dean 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? Learn more about your ad choices. Visit me...

Is Capitalism The Best We Can Do? | Surrounded Follow-Up 07.09.2025

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. Learn more about your ad choices. Visit me...

Patrick Bet-David vs 20 Anti-Capitalists 31.08.2025

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 v...

How Radical Is Amanda Seales? | Surrounded Follow-Up 24.08.2025

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Amanda Seales vs 25 Black Conservatives 17.08.2025

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 en...

Why Cenk Uygur Thinks It’s All One Big Scam 10.08.2025

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. Follow our YouTube channel:⁠https://www.youtube.com/@jubilee⁠...

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...

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