The Chicago Cubs have a lot of difficult decisions to make this offseason, and a mediocre free agent class will likely force them to pivot to the trade market.
Although trades are a smart way to fill some of the holes on this roster, the front office needs to be careful with who they move this winter. Last year, the team got burned after they traded Owen Caissie to the Marlins for Edward Cabrera. Caissie has the profile of being a power-hitting outfielder they could really use right now, while Cabrera failed to even stay in Chicago's rotation for the entirety of 2026.
To avoid a similar mistake, the Cubs should think twice about moving these top prospects.
Josiah Hartshorn
Hartshorn is currently the team's top minor leaguer, and no. 35 prospect in baseball according to MLB Pipeline. Hartshorn's rise came after a monstrous 2026 campaign, where he slashed .284/.407/.518 with 23 homers, 26 doubles, 91 walks, and 112 RBIs across three levels. The switch-hitting outfielder brings a little bit of everything to the table, including a high ceiling at the plate, thanks to his combination of plate discipline and power.
At only 19 years old, Hartshorn has the potential to be a key piece of Chicago's future. There's no guarantee he will pan out since he barely cracked the Double-A level last year, but this is a guy who could be a game-changer as soon as 2028. Trading him now risks losing out on much-needed offensive production from within the organization.
Owen Ayers
Developing catchers is no easy task, especially ones that can field and hit at a high level. And Owen Ayers proved he can do both last year. The 25 year old collected 55 extra-base-hits in 2026, including 29 doubles and 25 homers, along with 82 runs driven in. Those are phenomenal numbers for a catcher, and he also got on base with 82 walks over 125 games played.
The Cubs have Miguel Amaya for the foreseeable future, who is not a force at the plate and is more of a defensive catcher nowadays. Ayers is way too valuable to part ways with, even if his bat doesn't live up to the hype. Trading him would be a mistake, especially because it's not a guarantee that Carson Kelly returns next season.
Brooks Caple
Brooks Caple has risen to one of the most valuable arms in the Cubs' system after a breakout 2026 campaign. The former 9th-round pick made 21 starts between the South Bend Cubs (5) and Knoxville Smokies (16), with a solid 3.09 ERA and 108 strikeouts across 107 2/3 innings. He's only 24 and should make his way to Triple-A early next season, where he can hopefully bolster the Iowa Cubs' lackluster starting rotation.
Caple is a rising starter in a Cubs' farm system that is severely lacking at that position. The front office could cash in by moving him now, but they would jeopardize losing valuable starting pitching depth at a time where they need it most. Five major league starting pitchers are hitting free agency for the Cubs this winter, and we've seen how you need a lot more arms than that to make up for inevitable mid-season injuries.
