Surrounded

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...

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...

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...

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...

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. Learn mo...

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 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 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, 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...

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, 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...

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...

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...

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/...

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, 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...

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...

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

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 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...

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, 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...

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, 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...

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...