The Chicago Cubs won 92 games in 2025 and pushed Milwaukee until the final week, but their postseason push stalled because the flaws beneath the surface finally caught up with them. Shota Imanaga returning on the qualifying offer gives the rotation the stability it lacked down the stretch, and adding Phil Maton helps rebuild some late-inning structure. But Kyle Tucker leaving in free agency — after leading them in homers and OPS — leaves a glaring hole in the middle of the order. If the Cubs want to take the next step, the Winter Meetings must deliver impact, not just depth.
1. Reinforce the rotation behind Imanaga
Imanaga’s return doesn’t really solve the rotation problem. Too many innings were absorbed by patchwork starters in 2025, and a contender can’t live like that. Chicago has been linked to Michael King, and someone in that tier would prevent the club from riding a razor-thin margin again. With their lineup trending power-heavy last year, pitching remains the priority.
2. Replace Tucker’s production with a true middle-order threat.
Tucker’s exit didn’t just cost the Cubs home runs — it removed the left-handed bat that balanced the lineup and made opponents pick their poison. If Chicago can’t re-enter the bidding for a power bat in that tier, they’ll need to get creative. A corner infielder or outfielder with thirty-homer potential changes everything for an offense that spent too many nights stranding opportunities. Someone who hits behind their stars and forces pitchers into mistakes is essential.
3. Finish rebuilding the bullpen into a weapon again.
Maton is a good start, but Chicago can’t stop there. The bullpen worked too many high-stress innings last season, and it showed when the stakes climbed. One more high-leverage arm — someone who can bridge the gap to the ninth inning — would let the Cubs keep their starters fresher and shorten games the way contenders do. This team doesn’t need five new relievers; it needs one or two that matter.
The Cubs aren’t far away. One more rotation piece, a replacement for Tucker’s thunder, and a bullpen addition with teeth could finally give them the roster balance needed to win something more than the NL Central conversation. The Winter Meetings are where the Cubs can prove 2025 wasn’t their ceiling.
