Monday Morning Cubs Show

Setting Expectations For A Very Weird Cubs Winter


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Expect a strange winter on the North Side. We unpack why the Cubs’ path runs through pitching, controlled contracts, and a defense-first identity while the 2027 labor storm gathers on the horizon. With only Dansby Swanson guaranteed through that window and uncertainty around caps, floors, and tax dynamics, Jed and Carter look far more likely to trade for a top-three starter than drop half a billion on a right fielder. That’s not timid; it’s portfolio management in a volatile market.

We break down the fork in the road at DH and right field—Seiya Suzuki plus low-cost internal options like Moisés Ballesteros and Owen Caissie versus a megadeal that would throttle flexibility for a decade. Then we tilt to the rubber, where one dependable arm with control can stabilize Justin Steele, Cade Horton, and Jamison Taillon, and where the bullpen can be rebuilt with proven Cubs magic: one-year reclamations that turn stalled arms into multi-year paydays. Pair that with a team Gold Glove defense and you’re preventing runs at an elite level before spending a dime on slug.

Player arcs matter. Matt Shaw looks primed for a leap. Nico Hoerner, Dansby Swanson, and Ian Happ feel bankable. Michael Busch needs either real reps versus lefties or a no-doubt right-handed partner who mashes them—clarity now, not in August. PCA’s glove is already special; modest gains in swing decisions unlock real value. We also tackle the Shota Imanaga qualifying-offer clock and why process there could echo in future international recruiting.

Stick around as we riff on Wrigley hosting football, the Bears’ late-game surge with Caleb Williams, and five sharp differences between London and Chicago—from spotless pub bathrooms and tap-to-pay culture to architecture that feels like walking through a film set. Subscribe, drop a five-star review on Spotify or Apple, and share this one with a Cubs fan who loves smart roster talk. What’s your move: trade for a controllable starter or pay for power in right?

Thanks for tuning in!

- Carl & Mahoney

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Monday Morning Cubs ShowBy Carl + Mahoney

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