Surrounded
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 Trump Losing Support For The War? | Surrounded Follow-Up
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
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
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
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.
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1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded
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)
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.
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1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded
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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
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.
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1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded
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
Why Are Vegans So Annoying? | Jack Symes Surrounded Follow-up
Philosopher and author Dr. Jack Symes and John Regalado meet again to dissect Jack's Surrounded debate with 20 meat eaters. In this follow-up, they examine the moral weight of animal suffering, the scientific data behind plant-based longevity, and the controversial argument that modern food systems constitute a global moral crisis.
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1 Vegan vs 20 Meat Eaters (ft. Jack Symes)
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Vegan advocate Jack Symes enters the circle to face 20 meat-eaters in an intense debate about the ethics of our diets. In this episode of Surrounded, Symes navigates a deeply polarizing landscape, defending four uncompromising claims: that extreme suffering for
Top 5 Most Heated Debates | Surrounded
In this compilation episode of Surrounded, we revisit the most explosive and polarizing debates of the past year. One by one, these guests stepped into the circle to face 20 opposing voices in high-stakes clashes. Watch as Sam Seder takes on conservatives over DEI, Candace Owens defends traditional motherhood against feminists, Jordan Peterson clashes with atheists over morality and purpose, and m
Is Body Positivity Disempowering? Follow-up (ft. Jillian Michaels) | Surrounded
Fitness icon Jillian Michaels sits down with John Regalado and body positivity advocate Marcy Guevara to unpack the emotional fallout from her Surrounded debate. In this follow-up, they dive into the "primary wound" of childhood trauma, the conflict between movement loyalty and personal health, and why Jillian believes identifying as "fat" can become a psychological prison that hinders true libera
Jillian Michaels vs 20 Body Positivity Activists
Fitness trainer Jillian Michaels enters the circle to face 20 body-positivity advocates in a high-stakes debate about the future of wellness. In this episode of Surrounded, Michaels navigates a deeply personal and polarizing landscape, defending four core claims: the body-positivity movement is fundamentally disempowering, that the medical risks of obesity cannot be ignored, that large food corpor
Why It Always Comes Back to Butt Stuff | We Followed Up With Zander Moricz
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.
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1 LGBTQ+ Activist vs 25 Conservatives (ft. Zander Moricz)
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?
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Can Talarico Turn Texas Blue? | James Talarico vs 20 Undecided Voters Surrounded Follow-Up
John Regalado sits down with Texans Krista and Daniel, to revisit their Surrounded debate with James Talarico. In this follow up interview they discuss whether or not Talarico can truly deliver on the change he's promising, whether billionaires or ideology are dividing us, and what the point of voting is at all.
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Has the FBI Always Been Corrupt? | 1 Ex-Mafia Boss vs 20 Cops Surrounded Follow-Up
John Regalado is joined by retired FBI agent Tom and veteran police officer Heather to unpack the most revealing moments from their Surrounded debate with ex-Mafia Boss, Michael Franzese. In this follow-up interview, they dig into the deep mistrust between the American public and the FBI, why narratives of "hyper-partisanship" are damaging institutional integrity, and how the psychology of fear, e
Are Conservatives the Snowflakes Now? | Isaiah Martin Surrounded Follow-Up
Isaiah Martin sits down with John Regalado to unpack the most heated moments from his Surrounded debate with 20 MAGA Republicans. In this follow-up, they dive into immigration myths, Trump’s economic record, why Isaiah calls DOGE a failure, and how misinformation spreads in real time. Isaiah also reflects on what it’s like debating across deep divides—and what Democrats need to get right next.
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Isaiah Martin vs 20 MAGA Republicans
Isaiah Martin steps into Surrounded as the lone Democrat facing 20 MAGA Republicans. He challenges four core pillars of Trump’s agenda: that mass deportations make communities less safe, Trump serves the wealthy while leaving everyday Americans behind, DOGE was a complete failure, and Trump’s policies damage the economy. Will his arguments have an impact, or just reveal how wide the divide is?
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Has the Healthcare Industry Betrayed Us? | Doctor Mike Surrounded Follow-Up
John Regalado sits down with Bryan, Anastasia, and Jack to unpack the most revealing moments from their Surrounded debate with Doctor Mike. In this follow-up interview, they dig into the deep mistrust between everyday people and the medical establishment, why skepticism around Big Pharma keeps growing, and how lifestyle, diet, and personal responsibility collide with institutional medicine.
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Ex-Mafia Boss vs 20 Cops
Ex–mafia boss Michael Franzese steps into the Surrounded circle to face 20 cops in a rare role reversal. He challenges four core assumptions about modern policing: that undercover stings often manufacture crime, that law enforcement justifies breaking the law to catch criminals, that success is measured by arrests instead of safer streets, and that paid informants are deeply unreliable. Will his i
Gen Z’s Being Fed Fascism
Adam Mockler joins John Regalado to revisit the most charged moments from his Surrounded debate with 20 conservative college students. In this follow-up, Adam unpacks the rise of political extremism among young voters, how inflammatory rhetoric becomes normalized from the top down, why Trump’s “golden age” economy doesn’t hold up under scrutiny, and what real political courage might look like in
Adam Mockler vs 20 Gen Z Conservatives
It’s one liberal college dropout against 20 conservative college students. Adam Mockler steps into the Surrounded circle to defend four provocative claims: Trump is fueling a rise in fascism among young people, the economy is not in a so-called “golden age,” children are safer with the average undocumented immigrant than with Donald Trump, and Trump is the most corrupt president in U.S. history. C
Is Wokeness Really The Issue?
John Regalado sits down with Tyler, Jenny and Nick – participants from the Surrounded episode featuring Piers Morgan – to unpack the moments that sparked the most friction in their debate. In this follow-up, they dig deeper into their conversations around free speech absolutism, whether “wokeness” is truly authoritarian, the limits of cancel culture, and how media incentives and culture wars crowd
Why Gen Z Politics Have Become So Extreme
Tim Miller joins John Regalado to revisit some of the most thought-provoking moments from his Surrounded debate with 20 Gen Z conservatives. In this follow-up interview, Tim and John explore generational shifts on the right, how extreme immigration tactics and ICE enforcement become normalized, the moral tradeoffs of the Second Amendment, and even reflect on the famous Mehdi Hasan debate.
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James Talarico vs 20 Undecided Voters
Texas State Rep. James Talarico joins Surrounded to face 20 undecided Texas voters in a conversation about policy, power, and what’s at stake in 2026. He argues that cuts to healthcare and food assistance hurt everyone, that immigrants make America stronger and more prosperous, that every vote will matter next cycle, and that the real divide in politics isn’t left vs. right but top vs. bottom. Wil
Doctor Mike vs 20 RFK Jr. Supporters
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
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
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?
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Is Bryan Johnson's Immortality a Hoax? | Surrounded Follow-Up w/ Chelsea Gods & Bryton Snyder
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.
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Bryan Johnson vs 20 Skeptics
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
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
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.
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20 Boomer Trump Supporters vs 1 GenZ Liberal (ft. Luke Beasley) | Surrounded
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?
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Is There Only One Way to Read the Bible? | Surrounded Follow-Up w/ Allie Beth Stuckey
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.
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Allie Beth Stuckey vs 25 Liberal Christians
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?
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Are We Really Going To End All Abortions? | Surrounded Follow-Up w/ Lila Rose
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.
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Andrew Callaghan vs 20 Conspiracy Theorists
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?
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Lila Rose vs 25 Pro-Abortion Activists
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
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?
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Is Capitalism The Best We Can Do? | Surrounded Follow-Up
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 vs 20 Anti-Capitalists
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
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 vs 25 Black Conservatives
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
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 vs 20 Democrats & Republicans
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
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
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 vs 20 Liberal College Students
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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Is Candace Owens Living the Feminist Dream? | Surrounded Follow-Up
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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Destiny vs 25 Donald Trump Voters
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
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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20 Trump Supporters Take on 1 Progressive (feat. Sam Seder)
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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Doctor Mike vs 20 Anti-Vaxxers
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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A Palestinian Who Doesn’t Agree With Protestors | Ahmed Fouad Alkhatib Surrounded Follow-Up
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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20 Pro-Palestine Protestors vs Ahmed Fouad Alkhatib
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
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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1 Atheist vs 25 Christians (feat. Alex O'Connor)
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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Jordan Peterson vs 20 Atheists
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
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.
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1 Sports Analyst vs 25 NBA/NFL Fans (ft. Skip Bayless)
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?
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1 LGBTQ+ Activist vs 25 Conservatives (ft. Zander Moricz)
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?
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Surrounded Podcast | Show Trailer
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.
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