The Hangover w/ Pete Kaliner On The Brett Winterble Show

Tune in here to this Friday’s edition of the Brett Winterble Show! 

Brett kicks off the program with Pete Kaliner for this fist 2026 edition of the Hangover as they discuss the political future of New York City under its new mayor and what early warning signs could mean for his long-term ambitions. The conversation breaks down how long sweeping progressive promises—like free buses and expanded city services—can survive economic reality, especially when crises such as snowstorms or infrastructure failures test basic governance.

Pete explains why a mayor’s ability to handle day-to-day operations may matter more to voters than ideology, and how failure itself can become a political strategy. The discussion then widens to the national stage, examining divisions within the Democratic Party, the absence of clear establishment leadership, and how figures like AOC fit into that power shift. Brett and Pete also analyze how President Trump may selectively engage, choosing battles that resonate with “normie” voters. The segment closes with a sobering discussion of a recent ISIS-related terrorism case, highlighting warning signs, family intervention, and broader concerns about online radicalization.

Listen here for all of this and more on The Brett Winterble Show!

For more from Brett Winterble check out his YouTube channel.