Brett and Michael are back for the thirty-sixth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! With the baseball season nearing its end, the guys talk through a range of topics—from dominant postseason pitching performances to what lies ahead for the Cubs.

They start by discussing Trey Yesavage’s breakout playoff and World Series run, and where a pitcher with his stuff would have finished the year if he were a Cubs prospect—Double-A? Triple-A? The conversation expands into the growing league-wide trend toward promoting talented young pitchers earlier. With more arms entering pro ball already polished, are teams ready to embrace a true youth movement on the mound? And could future CBA changes accelerate that timeline even more?

The guys also dive into Jon Heyman’s report about the Cubs’ unwillingness to structure a Shohei Ohtani contract the same way the Dodgers did—with 97% of his record $700 million deferred. They unpack how that shaped the final bidding process, what the Cubs’ reported $500 million offer says about their strategy, and whether the Dodgers’ deferral-heavy model offered hidden tax benefits that helped seal the deal.

Finally, they reflect on where the Cubs stand in relation to true World Series contenders—what’s in place, what’s missing, and how far they really are from being the next team to make a deep October run.

A special thank you to Ankin Law for sponsoring this podcast!
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