As the 2025 MLB offseason approaches, the Chicago Cubs face crucial decisions after being eliminated from playoff contention. In this week’s episode of Bricks Behind the Ivy, we break down the 3 big questions the Cubs must answer this offseason: What’s next for the roster, how should they approach free agency, and what’s the future of the coaching staff?

Plus, we lighten the mood with “Deep Thoughts with Harry Caray,” a special check-in from the legendary Cubs announcer. Even though the Cubs didn’t make the postseason, we’re here to bring you all the Cubs updates and a little fun along the way.

Bricks Behind the Ivy is a weekly Cubs podcast for Cubs fans, by Cubs fans, covering all the latest news, insights, and analysis.

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