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Brian Wolff

Democratic strategist with experience working on Capitol Hill and for House Democrats, providing political analysis and perspective for the episode.

Top 3 podcasts with Brian Wolff

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10 snips
Dec 11, 2025 • 1h 2min

Trump Announces Seizure of Oil Tanker near Venezuela, Demands CNN Be Sold as Part of Any WBD Deal

Guests Todd Ricketts, a businessman and co-owner of the Chicago Cubs, and Brian Wolff, a seasoned Democratic strategist, dive into the current political landscape. They discuss Trump's comments on the U.S. seizure of an oil tanker near Venezuela and the potential legal implications. The conversation also explores economic concerns, with insight into the Federal Reserve's decisions. Additionally, they evaluate the political motivations behind Trump’s call to sell CNN amid ongoing debates about the 2028 Democratic favorites. It’s a lively exchange filled with sharp analysis!
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Oct 10, 2025 • 1h 2min

2WAY TONIGHT | Mark Halperin on Trump’s Second Term, the Democrats and the Latest Political News

Joining Mark Halperin are Jeff Roe, a Republican strategist with extensive campaign experience, and Brian Wolff, a Democratic strategist and former Hill operative. They dive into the implications of Trump's potential second term and analyze the recent Middle East breakthrough, including its next steps. Tensions rise as they tackle government shutdown negotiations and dissect the Texas Senate race landscape. The discussion heats up with listener questions on immigration messaging and the impact of legal battles surrounding federal deployments. An insightful bipartisan dialogue!
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Sep 17, 2025 • 57min

Jimmy Kimmel Show Suspended After Kimmel Blames "MAGA Gang" for Charlie Kirk's Death; Probe Latest

Brian Wolff, a Democratic strategist known for his progressive insights, and Elizabeth Pipko, a Republican commentator and activist, engage in a lively discussion on recent political turmoil. They analyze the fallout from Charlie Kirk's tragic death, reacting to media coverage and notable comments from figures like J.D. Vance and Barack Obama. The conversation takes a turn as they tackle the responsibilities of tech platforms and the implications of Jimmy Kimmel's controversial remarks, navigating rising political violence while pushing for accountability and unity.

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