It's safe to say the season ended worse than the Chicago Cubs anticipated. They underperformed and wasted a huge opportunity. Simply put, they need to be better. With that in mind, expect major turnover. The revamp will take time, and the organization needs improvement in multiple areas, including the farm system.
However, focusing on the major league roster: The starting rotation has obvious holes , the bullpen is a mess , and numerous players can re-sign or walk. No one knows what the off-season will bring, but the Cubs do have several position players they should consider trading to upgrade the team.
Let's review one name who could net them the biggest return.
Sep 19, 2026; Cincinnati, Ohio, USA; Chicago Cubs outfielder Matt Shaw (6) walks off the field in between innings against the Cincinnati Reds at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images | IMAGN IMAGES via Reuters Connect
Look, there's no easy way to say this, but Matt Shaw is as inconsistent as clothing sizes. He has had his fair share of good moments, but nothing has ever stood out. With the core group locked up, Shaw is a top-bench player/utility role guy. The Cubs should easily be able to find those types of players in the open market.
Shaw is a right-handed batter who, in two seasons with the Cubs, has a .230 batting average, 18 home runs, and 68 runs batted in. He's also appeared in only 185 games in his career, so some teams can almost surely give him more consistent opportunities. Not to mention, as a first-round pick taken by the Cubs in the 2023 MLB Draft, the potential to grow into more is still there.
Speaking of which, what arguably stands out more about Shaw is his age. He's still only 24, so might several teams be willing to see if he's got more to prove? Teams in rebuilding mode can bet on that age.
He has played numerous positions, including both corner outfield spots, second base, and shortstop. Before the Cubs signed Alex Bregman, Shaw was the starting third baseman.The potential to do that somewhere else is possible. If the Cubs do decide to trade Shaw, who would take him? How about a team that you worked with at the trade deadline? The familiarity is something to note.
Sep 14, 2026; Anaheim, California, USA; Los Angeles Angels pitcher Reid Detmers (48) throws against the Seattle Mariners at Angel Stadium. Mandatory Credit: Kirby Lee-Imagn Images | IMAGN IMAGES via Reuters Connect
The Los Angeles Angels are rebuilding. The Cubs already acquired bullpen arm Ryan Zeferjahn from them at the trade deadline, which meant trading away Moises Ballesteros and Mason McGwire, who was a top-30 prospect.Might this mean the two sides are open to doing business again this winter?
Moving Shaw in a deal for starting pitcher Reid Detmers, who the Cubs were closely tied to this trade deadline, could make a lot of sense for both sides. To be sure, Shaw alone likely wouldn't get the deal done. The Cubs would need to add at least a couple more pieces to get the Angels to bite.James Triantos, Jaxon Wiggins, Caden Sorrell, and Kane Kepley are some of the Cubs' other top prospects who would be worth monitoring in this situation.
Nevertheless, adding a starter of Detmers' caliber would be a huge addition to the rotation. Still only 27 years old with multiple seasons of team control, Detmers had a 3.36 ERA over his 32 starts in 2026. He would give the Cubs the kind of swing-and-miss guy they have often lacked, holding a 28.5 K rate this past season, as well as a 29.1 percent whiff rate. Even better, he did it while recording a career-best walk rate.
The Cubs are on the brink of potentially losing multiple starting arms, including Kevin Gausman, Clay Holmes, and Shota Imanaga. Would moving on from Shaw be the easiest decision in the world? No, but Detmers is the kind of proven piece that makes you consider a deal.
Add Detmers, and the Cubs are now taking meaningful steps toward rebuilding the rotation. Especially if they can add a high-profile free-agent signing , a healthy Cade Horton, and Justin Steele, the Cubs would have the makings of a very competitive unit in 2027.
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This article was originally published on www.si.com/mlb/cubs/onsi as One Cubs Player Likely to Be in Trade Rumors This Winter (And Who Might Be a Target) .
