If the Cubs were as good at scouting and player development as they keep telling fans (and themselves) they are, they’d have a pretty simple offseason ahead. They’d have amassed better homegrown pitching depth, and wouldn’t be so obviously starved for swing-and-miss arms. They’d be in a position to place much more trust in their young bats, from the relatively established (Pete Crow-Armstrong, Miguel Amaya and Matt Shaw) to those still breaking slowly into the rotation (Kevin Alcántara, Moisés Ballesteros, and Owen Caissie). As things stand, though, they’re in no position to compete with the Brewers in the NL Central—let alone to make a deeper push into October—without a significant talent infusion from outside the organization.

Kyle Tucker is likely to sign elsewhere this winter. He’s in line for a contract in excess of $300 million, partially because of his talent and partially because other options in free agency are fairly limited this year. The Cubs will have to replace his production just to get back to where they were this past season, and while that production is more replaceable than it appeared it would be around Memorial Day, it’s still one of the two titanic challenges of their offseason. The other, of course, is getting up to speed (literally, in part) with better pitching talent.

Reunions with Kyle Schwarber or Cody Bellinger are “extremely unlikely,” according to league sources, and those fits would be imperfect, anyway. It’s much more likely that the Cubs let Seiya Suzuki retake his place in right field in 2026, with Caissie or Ballesteros sliding in as the long side of a platoon at DH and occasionally spelling Suzuki or Ian Happ in an outfield corner. Alcántara is ready to play at least a complementary role in the majors, too, and could be both the platoon partner to Crow-Armstrong and a versatile weapon to shield Happ, Caissie and/or Ballesteros from difficult matchups.

The more plausible (and perhaps wiser, anyway) path to a major infusion of offensive value might be a splurge at the hot corner. Alex Bregman reportedly plans to opt out of the last two years of his three-year, $120-million deal (in reality, after accounting for deferrals, worth much less than that) with the Red Sox, and will be a free agent for the second year in a row. Eugenio Suárez will also be a free agent at the end of the World Series. Bregman, 31, was worth 17 runs above an average hitter in 495 plate appearances this year, according to Baseball Reference. Suárez, 34, was 20 runs above average in 657 trips to the dish. 

Either player would command a big deal this winter, though of course, Bregman’s would be a much longer-term and more lucrative engagement. Age and a streakier profile will limit Suárez’s earning power a bit. Nonetheless, each had a season very much in line with their prime production in 2025. Bregman’s DRC+ (the holistic offensive value metric from Baseball Prospectus; 100 is average, higher is better) was 117 this year and is 116 for his career; Suárez’s 2025 DRC+ of 105 is identical to his career mark. While neither is a defensive wizard at third base, each figures to stick there and acquit themselves well for a few more years.

Speaking of defensive wizards, entertaining signing either of the two star third basemen invites the question: What becomes of Matt Shaw? It’s a fair one. The Cubs should, if they can, include Shaw in a package for a starting pitcher this winter. Though he made some admirable adjustments along the way, ultimately, Shaw’s rookie season was a major disappointment to anyone who held out much hope for him as a hitter—and, for those of us who doubted him, a seeming confirmation. Shaw’s combination of smallish stature, unorthodox mechanics and a disorganized approach left him with an 87 DRC+ for the season, and he was utterly overmatched in the postseason. He could settle in as a fine utility man without making significant strides from here, but that wouldn’t help the Cubs much. He should have more upside than that, if he can develop on a steady arc into his mid-20s, but that’s not guaranteed—as his extremely uneven first season showed.

Without question, Shaw still has some trade value. It’s unlikely that he could headline a deal for a pitcher like Edward Cabrera, Sandy Alcántara, or Pablo López, but he could be a strong second piece alongside one of the lefty bats (Caissie and Ballesteros) whom teams believe in more as hitters, or as a co-headliner with a player further from the majors. The Cubs need more power at the plate, and they need to bolster their pitching staff. To do both, in a winter with a thin free-agent class and major financial uncertainty looming for the sport, they need to be active in both the trade and free-agent markets. Dealing Shaw and signing either Bregman or Suárez would be the best way to plunge ahead.