

Surrounded
Jubilee Media
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
Mentioned books

Aug 10, 2025 • 1h 8min
Why Cenk Uygur Thinks It’s All One Big Scam
Cenk Uygur, co-founder of The Young Turks and a vocal progressive, joins John Regalado to dissect the political landscape. They discuss how both Republicans and Democrats cater to donors, labeling the system as a scam. Cenk critiques identity politics and the need for Democrats to adopt a genuine populist approach. He expresses frustration over unfulfilled promises by Democratic leaders and highlights the growing disconnect between political elites and everyday citizens. The conversation also addresses the challenges of diversity initiatives and the potential for a third political party.

Aug 3, 2025 • 1h 44min
Cenk Uygur vs 20 Democrats & Republicans
Cenk Uygur, a Turkish-American political commentator and co-founder of The Young Turks, passionately debates 25 Democrats and Republicans on fundamental issues. He argues that both parties often sidestep critical economic concerns through culture wars, pointing out that the Democratic agenda leans more on marketing than real change. He claims corporate money dominates political power, serving the wealthy's interests over the working class. The discussion challenges listeners to rethink activism and political engagement in a climate of misinformation.

Jul 26, 2025 • 1h 11min
Can 1 Cop Defend Himself Against 20 Criminals? | Surrounded
Kevin Donaldson, a retired New Jersey police officer, engages in a thought-provoking dialogue with 20 individuals who have criminal records. They tackle critical issues of police accountability and the use of lethal force. Donaldson defends claims of officer honor and integrity, while discussing the complexities of racial profiling and public perception. The conversation dives deep into necessary reforms in policing training and emphasizes the importance of community trust. Can understanding bridge their vastly different experiences?

21 snips
Jul 20, 2025 • 1h 42min
Mehdi Hasan vs 20 Far Right Republicans
Join Mehdi Hasan, a progressive journalist known for his sharp political insights, as he confronts 20 far-right Republicans in a heated debate. He boldly asserts that Trump is pro-crime and defies the Constitution. The discussions span immigration's pivotal role in America, the validity of presidential pardons, and the nuanced complexities of the Gaza conflict. Hasan delves deep into issues of citizenship, democracy, and accountability, challenging opposing views with fervor and well-researched arguments, all while navigating a politically charged atmosphere.

Jul 13, 2025 • 1h 35min
Charlie Kirk vs 20 Liberal College Students
In this lively discussion, Charlie Kirk, founder of Turning Point USA and known for his conservative activism, faces off against a group of 20 liberal college students. He passionately defends controversial views, claiming abortion is murder and asserting that college is a scam. The debate about gender identity heats up as Kirk challenges the notion of trans women being women. Topics also include the implications of Kamala Harris's DEI candidacy and a critical look at the value of college education in today’s economy. Expect fiery exchanges and thought-provoking arguments!

11 snips
Jul 6, 2025 • 35min
Is Candace Owens Living the Feminist Dream? | Surrounded Follow-Up
Candace Owens, a cultural and political commentator known for her conservative stance, joins John Regalado for a thought-provoking discussion. They reflect on her recent debate with feminists, diving into her perspectives on feminism, motherhood, and societal expectations. Owens challenges traditional views on women's fulfillment, arguing that authentic choices matter more than societal definitions of success. The conversation also explores shifting gender roles and the impact of modern feminism on family dynamics, all while navigating the complexities of content creation.

9 snips
Jul 3, 2025 • 2h 2min
Destiny vs 25 Donald Trump Voters
Destiny, a well-known online streamer and political commentator, engages in an intense debate with 25 Trump supporters. He presents bold claims about Trump’s fitness for presidency and contrasts his policies with Kamala Harris's immigration plan. The discussion dives into the Capitol riot's implications, the complexities of U.S. immigration laws, and the economic impacts of both administrations. Through fiery exchanges, Destiny challenges misinformation and highlights the importance of civil discourse in political debate.

9 snips
Jun 29, 2025 • 1h 41min
Candace Owens vs. 20 Feminists
In a riveting discussion, Candace Owens, a provocative political commentator and author, takes on 20 feminists about the implications of feminism and societal norms. She argues that the sexual revolution may have devalued women and asserts that motherhood can be more fulfilling than a career. They debate whether we truly live in a matriarchy and whether feminism has made life easier for men. The conversation navigates the balance of work and family, empowerment, and the changing roles of women in society, stirring a dynamic clash of ideas.

Jun 22, 2025 • 1h 33min
20 Trump Supporters Take on 1 Progressive (feat. Sam Seder)
Join Sam Seder, host of The Majority Report and a fierce advocate of progressive values, as he stands against a group of 20 Trump supporters. They delve into Trump's controversial DEI policies, suggesting they're a cover for corporate interests. Seder argues that voting for Trump benefits only the wealthy, questioning the future of Social Security and healthcare. The debate touches on gender identity, poverty alleviation through tax reforms, and the broader implications of America's cultural identity under the Trump movement.

7 snips
Jun 17, 2025 • 1h 33min
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. Learn more about your ad choices. Visit megaphone.fm/adchoices