Surrounded

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In this episode of Surrounded, commentator David Mauricio from The Split steps into the hot seat as one liberal voice facing off against 20 MAGA debaters.

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Andrew Yang faces 20 AI optimists in Jubilee’s Surrounded, defending four provocative claims: AI will accelerate inequality, eliminate jobs faster than new ones can emerge, make Universal Basic Income necessary, and push markets to prioritize profit over human dignity. Will Yang’s warnings withstand the optimism—or will the AI believers dismantle his case?

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Austin Julio Broughton steps into the hot seat on Jubilee’s Surrounded to defend four incendiary claims against 20 Liberals: The Left cares more about LGBTQ+ issues than Black Americans. Elective abortion is modern America’s greatest moral failure. Civil rights were won with Bibles and churches, not pronouns and DEI. Republicans care more about free speech than Democrats. Will Austin hold the line against overwhelming odds, or will the room shut him down?

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Maxwell Frost takes center stage in Jubilee’s Surrounded, facing off against 20 Boomers to defend four hard-hitting claims: Gen Z is the most politically active generation in American history, they aren't too spoiled or lazy, all student debt should be canceled, and while Boomers lived the American Dream, Gen Z can only read about it. Can the youngest member of Congress hold his own against a room full of seasoned skeptics, or will the generational divide prove too wide to cross?

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Tim Pool steps into the ring with 20 progressives in this explosive episode of Jubilee’s Surrounded. Standing alone as the sole moderate voice, Pool defends four radical premises: the mainstream left commits more violence than the mainstream right, the Democratic Party has fully embraced authoritarianism, America is actively heading toward a civil war, and the U.S. Constitution effectively no longer exists. Will Tim withstand the crossfire, or will the consensus collapse his defense?

On this week's episode, Officer Brandon Tatum joins host Parris Rose to recap Tatum's time in the Surrounded Circle. They discuss several clips with the guest debators, and break down some of the most heated moments of the discussion.

Officer Tatum steps into the center of Jubilee’s Surrounded to take on 20 Black Liberals in a high-stakes debate over race, politics, and responsibility. He stands alone to defend four explosive claims: Trump and the GOP are better for the Black community than Democrats, police do more good than harm, Black-on-Black crime is the most critical threat, and systemic racism is used as an excuse to avoid personal accountability. Will Tatum hold his ground under heavy fire, or will the panel dismantle his conservative playbook?

Mark Manson steps outside the circle to unpack his debate with 20 manosphere creators. Is the manosphere helping men—or trapping them in an echo chamber of insecurity? What We Unpack in This Episode The Looksmaxxing Trap: Why hyper-focusing on superficial traits turns dating into a transaction—and leaves men feeling more isolated than ever. Echo Chambers vs. Reality: How the manosphere monetizes male insecurity and converts genuine loneliness into online hostility. The Middle School Mindset: Uncovering why so many digital "alphas" struggle to build lasting, adult relationships. Redefining Modern Masculinity: What self-improvement actually looks like when you strip away the posture, the performance, and the podcasts.

Mark Manson steps into the circle against 20 manosphere creators in Jubilee’s Surrounded, defending four hard-hitting claims: the manosphere is a predatory business profiting off male anger, a woman's body count is irrelevant, porn has ruined men far more than feminism, and true attractiveness stems from respecting women. Will Manson dismantle the echo chamber with reason, or will the pack overrun him? They debate the 4 following claims that Mark Manson, has: 1. The manosphere is a business that profits off keeping men angry, 2. A woman's body count doesn't matter, 3. Porn has done more damage to men than feminism has, 4. The most attractive men are those who respect women

John Regalado sits down with non-voter Carlheb to unpack their recent Surrounded debate with Wes Moore. In this follow-up, they discuss the moral tension that comes with participating in an imperfect and often corrupt system, the legacy of slavery in the current political consciousness, the influence of black revolutionaries like Fred Hampton, and whether or not Wes Moore convince Carlheb to cast his vote in future elections.

Democratic leader Wes Moore faces 20 non-voters in a compelling episode of Surrounded, tackling political disillusionment head-on. He challenges the room with three urgent claims: 1) nothing shapes policy more effectively than your vote, 2) bad politics thrive when citizens don’t participate, and 3) abstaining from the ballot protects corruption rather than protesting it. Can Moore convince a skeptical crowd to reclaim their civic power, or will their disillusionment prove too deep to overcome?

John Regalado sits down with Lori and Julia Kate to unpack their viral Surrounded debate with Dean Withers. In this follow-up, they dive deeper into their personal backgrounds and values, their perspectives on Donald Trump, and discuss the discourse of modern political commentary.

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Kyla Turner steps outside the circle to join John Regalado in this follow-up to the viral Dave Rubin Surrounded debate. In this discussion, Kyla shares her perspective on the debate – covering the perceived contradictions of Rubin's political alignment and identity, political extremism in American politics, economic metrics under the Trump administration and the necessity for political accountability and effective governance across the political spectrum.

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 corruption within the Trump and Biden administrations, and who Mat sees as the potential political leaders for the 2028 election.

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 moderate Americans to the right, and that the modern left prioritizes ideology over reality. Can Rubin’s blunt critiques challenge the room's core convictions?

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 strikes on Iran would be a disaster for the American people. Will his relentless critiques force a reckoning, or can the room defend their champion?

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.

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 overwhelmed rather than broken, hopelessness is a symptom not a final conclusion, deep depression can coexist with productivity and success, and past therapy failures don’t mean you are beyond help.

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.

Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us! 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: that Israel is not committing genocide or apartheid, that anti-Zionism equates to anti-Semitism, that Jews are indigenous to Israel, and that Zionism is a movement of decolonization. As historical trauma meets fierce human rights arguments, can Rochman find a path to mutual understanding with his critics?

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.

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, and the U.S. must finally hold its powerful elites accountable. In a space where demands for political transparency clash with fractured public trust, can Khanna find common ground with his critics?

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.

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 trivial pleasure is morally indefensible, that everyone should aim to be vegan, that factory farming ranks among the worst atrocities in history, and that veganism is fundamentally good for the world and humanity. In a space where personal lifestyle clashes with moral obligation, can Jack’s perspective find common ground with his critics, or are the divides too deep to bridge?

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 more.

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 liberation.

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 corporations are capitalizing on the movement, and that current discourse oversimplifies the complexities of disordered eating. The group then debates a counterclaim: that shame remains a greater threat to health than the movement itself. In a space where personal identity meets public health, can Jillian’s perspective find common ground with her critics, or are the divisions too deep to bridge?

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://x.com/odalager_j⁠ ⁠https://www.youtube.com/@j_regalado

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://www.youtube.com/@jubilee⁠⁠ Follow Zander Moricz & SEE Alliance: ⁠⁠https://www.instagram.com/zandermoricz⁠⁠ ⁠⁠https://seeourpower.org⁠⁠ ⁠⁠https://x.com/zandermoricz⁠

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.

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, empathy, and the heavy toll of service collide in modern policing.

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.

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?

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.

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 insider perspective expose uncomfortable truths—or be shut down by those sworn to uphold the law?

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 2026.

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. Can one outsider hold his ground against a room full of undergrads?

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 out material issues like wages, housing, and healthcare.

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.

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. Will his message resonate with voters still on the fence?

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 politics—not health. Can medical expertise cut through the skepticism?

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?

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.