Bobby and Alex discuss MLB’s fluctuating October slogans and decide whether “There’s No Time Like October” is actually pretty good, all things considered. Then, they check in on the status of the Championship Series and recap some Division Series action. Finally, they check in about the latest MLB CBA proposals, which included a shortened season, extended playoff series, and more.

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Tipping Pitches features original music from Steve Sladkowski of PUP.

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.

Links:

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.

Bobby and Alex react to some long-awaited news about the sand in beautiful Malibu, California. Then, they review the status of the 2026 Tipping Pitches Bingo Card, before being joined by Ringer Senior Features Writer Katie Baker to discuss her piece on Dodgers owner Mark Walter. They discuss the financial circles he comes from, his myriad private equity connections and business pursuits, his style of business leadership, and more.

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Read Katie’s piece on Mark Walter in The Ringer

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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 Pablo Torre and Hunterbrook’s investigation into Dodgers owner Mark Walter’s alleged self dealing, including what it portends (if anything) for the future of the team. Then, they briefly discuss the NBA’s punishment of Steve Ballmer and the Clippers, before publishing the Angels segment of The Audit Episode Five, which will run in full on Patreon in two weeks.

Links:

PTFO’s episode on Mark Walter and Magic Johnson

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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 gather for this mini reaction episode to discuss the surprising sale of the Los Angeles Angels to billionaire serial sports owner Stan Kroenke. First, they grade the Arte Moreno era on his on and off field performance, before bidding him (and his FBI bribery investigation) adieu one final time. Then, they weigh in on Kroenke’s ownership experience, his frankly absurd real estate portfolio, his Walmart ties and more. Finally, they speculate about what the timing of the sale might signify about the economic health of Major League Baseball ahead of a contentious lockout in three months.

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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 Chris Sale turning back the clock and what the podcaster equivalent would be, before assessing MLB’s current labor strategy of proposing as many anti-player policies as policy in the hopes that one will stick. Then, they’re joined by Great Friend of the Show Jen Ramos Eisen to do a deep dive into the state of the Women’s Pro Baseball League, with a particular focus on the financial management (or lack thereof) of the league thus far.

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Call the Tipping Pitches voicemail: 785-422-5881

Tipping Pitches features original music from Steve Sladkowski of PUP.