Surrounded

Latest Episodes:

1 Liberal vs 20 MAGA (ft. The Split’s David Mauricio) | Surrounded Oct 11, 2026

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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.

Evan Revisits His Most Viral Debates | Surrounded Follow-Up Oct 04, 2026

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TIMECODES
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03:07 Clip 1
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Andrew Yang vs 20 AI Optimists | Surrounded Sep 27, 2026

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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?

Is This Conservative Actually Pro-Reparations? | Surrounded Follow Up Sep 20, 2026

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1 Conservative vs 20 Liberals (ft. The Split’s Austin Julio Broughton) | Surrounded Sep 13, 2026

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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?

Gen Z and The American Dream | Surrounded Follow Up w/Maxwell Frost Sep 06, 2026

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1 Young Politician vs 20 Boomers (ft. Maxwell Frost) | Surrounded Aug 30, 2026

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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?

Tim Pool vs Progressives | Surrounded Follow-Up Aug 19, 2026

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1 Moderate vs 20 Progressives (ft. Tim Pool) Aug 16, 2026

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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?

Is Trump Better for Black Americans Than Democrats? | Surrounded Follow-Up w/ Officer Tatum Aug 09, 2026

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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.

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