Bobby and Alex discuss the [redacted] market Rays and Brewers looking like October powerhouses in their respective division series vs. the big bad New York Yankees and high-payroll San Diego Padres, respectively. Then, they zoom out and discuss the brand of baseball being played this October thus far, and the unique weirdness of the MLB postseason. After that, they’re joined by Tom Sexton of Trillbilly Workers Party to discuss the proliferation of prediction markets like Kalshi and Polymarket in professional sports — what does it mean for the integrity of the game, addiction in society at large, and the general malaise that’s begun to blanket American sports.

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Call the Tipping Pitches voicemail: 785-422-5881

Tipping Pitches features original music from Steve Sladkowski of PUP.

Bobby and Alex discuss Max Scherzer and Justin Verlander's twin flame careers and Scherzer's incredibly on-brand final game of 2026 (and maybe ever). Then, they briefly dig into Pablo Torre Finds Out's report about Life Surge — a potentially fraudulent Christian investment conference that has worked with pro athletes like Tim Tebow and David Ortiz. Finally, they react in real time to the MLB playoff bracket being set and make their World Series predictions.

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Call the Tipping Pitches voicemail: 785-422-5881

Tipping Pitches features original music from Steve Sladkowski of PUP.

Bobby and Alex speculate on what Rob Manfred gets paid as commissioner of baseball. Then, they discuss a handful of interesting quotes coming from a letter written by a Braves minority investor and the lackluster playoff bracket on the American League side. Finally, they're joined by author and journalist Julie Kliegman to discuss their biography of trans tennis trailblazer Renée Richards and the book's resonance with our current climate around trans athletes.

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Buy "Finding Renée Richards"

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Call the Tipping Pitches voicemail: 785-422-5881

Tipping Pitches features original music from Steve Sladkowski of PUP.