The Cubs’ disappointing finish has already pushed the front office toward a winter of change, and one of the most interesting names to watch is Matt Shaw. Chicago has plenty of issues to sort through - a rotation with obvious holes, a bullpen that needs help, and uncertainty across the roster - but Shaw stands out as the kind of player who could be used to address one of the club’s biggest needs.
Shaw hasn’t made himself untouchable. In two seasons with the Cubs, the right-handed hitter has posted a .230 average with 18 home runs and 68 RBIs across 185 games.
He’s shown flashes, but nothing that firmly locks him into a long-term role, especially with the core group already in place. At the same time, there’s still appeal here: he was a first-round pick by the Cubs in the 2023 MLB Draft, and he’s only 24.
His versatility only adds to the conversation. Shaw has played both corner-outfield spots, second base and shortstop, and before the Cubs signed Alex Bregman, he was their starting third baseman. That kind of defensive flexibility makes him useful, but it also makes him the sort of piece a rebuilding team might value more highly than a club with a deeper major league roster.
If Chicago does decide to shop him, the Los Angeles Angels could be a natural fit. The two teams already lined up on a trade deadline deal when the Cubs got Ryan Zeferjahn from Los Angeles in exchange for Moises Ballesteros and Mason McGwire, a top-30 prospect. That previous business could matter if the Cubs and Angels circle back this winter.
One possible framework would involve Reid Detmers, a pitcher the Cubs were closely linked to at the deadline. Shaw by himself probably wouldn’t be enough to land him, so Chicago would likely need to add more pieces to make it work. James Triantos, Jaxon Wiggins, Caden Sorrell and Kane Kepley are among the Cubs prospects worth watching in that kind of conversation.
Detmers would bring a lot to the table. He’s still just 27 and has multiple seasons of team control, and he turned in a 3.36 ERA over 32 starts in 2026.
The swing-and-miss profile is the big draw: a 28.5 K rate and a 29.1 percent whiff rate, plus a career-best walk rate. For a Cubs staff that has too often lacked that type of arm, it’s an enticing fit.
That need only grows if Chicago loses multiple starters, with Kevin Gausman, Clay Holmes and Shota Imanaga all potentially on the way out. Trading Shaw wouldn’t be a painless call, but a move like this would give the Cubs a real shot at strengthening the rotation.
And if they pair a deal like that with a high-profile free-agent signing, a healthy Cade Horton and Justin Steele, the pieces could start to come together for a much more competitive 2027 rotation.
In Other News...
Jed Hoyers Biggest Cubs Problem Could Finally Look Very Different
The Cubs pitching picture beyond this season is already starting to take shape, and it looks a lot different from the one fans have been watching lately. Several of the names in the projection for 2027 are veterans or newcomers who would give Chicago a more stable-looking rotation on paper, with Sonny Gray, Clay Holmes, David Peterson, Justin Steele and Edward Cabrera all emerging as possible pieces if the front offices thinking holds.
What makes the exercise interesting is how much of the current staff could be in flux by then, with a number of pitchers headed for free agency and the club expected to keep pouring offseason resources into the mound. Jed Hoyer has made clear where the priority lies, and if the Cubs follow through, the most glaring roster issue could end up looking very different in just a couple of years, even if the exact mix of arms is still a work in progress. [Read more 🡒]
Cubs Just Hit A Potential Snag In Their Pitching Search
The Cubs are heading into an offseason where pitching is likely to be the main priority, with the front office expected to look for arms that can keep the ball on the ground and still miss bats. With several rotation spots in 2027 projected to come from outside the organization, the team figures to be active in the market, and Trevor Rogers has the kind of profile that fits what Chicago is after.
Rogers 2026 season with Baltimore was steady enough to keep him on the radar, especially with a 3.45 FIP backing up a 4.03 ERA, but his groundball rate dipped compared to previous years. The wrinkle for the Cubs is that the Orioles may extend a qualifying offer, and under the current CBA that could make any pursuit more expensive and more complicated than Chicago would like. [Read more 🡒]
Jed Hoyer Faces A Familiar Cubs Trap In This Pitching Search
The Cubs are again in the market for pitching help, and the names at the center of the discussion all come with a familiar warning label. Shane Bieber, Casey Mize and Bryan Abreu each carry some version of the same risk profile that has tripped up clubs before: recent health issues, uneven performance or a fastball that simply does not look as sharp as it once did. For a front office trying to build stability on the mound, those are the kinds of questions that can turn a promising winter into a costly detour.
Jed Hoyer has seen this movie before, when upside and pedigree made it easy to talk a team into believing a bounce-back was around the corner. Biebers health and performance concerns, Mizes declining velocity and Abreus dip in fastball speed along with a higher walk rate all make for tempting but dangerous projections. The Cubs can afford to dream on arms with upside, but this offseason suggests a need for more caution than nostalgia. [Read more 🡒]