The Chicago Cubs have been one of the most confusing teams in baseball this year, with far and away the best positional group in the sport when it comes to both offense and defense that's held back by a pitching staff that's among the worst in the league. For now, the focus for the Cubs is trying to get through the Wild Card race unscathed. Headed into the offseason, however, Chicago's front office has some big decisions that will need to be made.
The entire current starting rotation is slated to hit free agency when the season ends, and they'll be joined by Ian Happ, Seiya Suzuki, and Carson Kelly from the offense. That leaves a lot of holes to fill this winter, and while some of them could be filled by re-signing departing players or with internal options, there will need to be some external replacements brought in. Barring a shock run at Tarik Skubal this winter, free agency looks weak, so the team will have to consider trades.
Enter Matt Shaw, who was a popular trade candidate this past offseason after he was displaced from the regular third base job by the Alex Bregman signing. The Cubs ultimately did not pull the trigger on moving him, instead moving him into a utility role where he's primarily played against left-handed pitchers. Despite injuries limiting him to this point in the season, Shaw has done well by playing adequate defense all over the diamond with impressive offense (115 wRC+) for a bench bat.
There are some red flags, however. Even beyond fear of further injuries, Shaw's peripheral numbers create questions about his success's sustainability. A .305 xwOBA is more average than exceptional, and his career 84 wRC+ against righties won't cut it in the outfield as a full-time player. That might mean the Cubs are best served trying to deal him this offseason to help the rotation, but which teams would be the best matches? Here's three fits, plus the pitchers the Cubs could seek in return:
Could the Cubs take advantage of the Mariners' crowded rotation?
The Mariners finally made their long-awaited trade of a veteran from their rotation this summer when they shipped Luis Castillo to the White Sox. Even after that trade, they still have more starters than they can use. Top propect Kade Anderson burst onto the scene this year, joining veterans George Kirby and Logan Gilbert as well as younger arms like Bryce Miller, Bryan Woo, and Emerson Hancock. Ryan Sloan and Logan Evans are also options for 2027, giving Seattle eight starters.
The Mariners reportedly dangled both Kirby and Hancock in trade talks over the summer, and while deals involving neither came together it's certainly possible they'll be revisited this offseason. Shaw would make a ton of sense heading to Seattle in return, as the club has struggled badly against lefties this year and will have a hole on the infield when J.P. Crawford leaves via free agency. Cole Young at second base, Colt Emerson at shortstop, and Shaw at third would be an exciting future for Seattle.
Matt Shaw would be the perfect fit for a beleaguered Blue Jays offense
After finishing 2025 season in heartbreaking fashion, the Blue Jays went big this offseason. Unfortunately, they were not rewarded for it and appear poised to miss the playoffs this year. The club clearly needs to make changes, and they started that process with a number of sell-side trades this summer, including the deal that sent Kevin Gausman to the Cubs. While that trade hasn't worked out the way fans hoped it would, perhaps another Toronto pitcher could be a better fit.
The Cubs not only pursued Angels righty Jose Soriano before he was traded to the Blue Jays this summer, but they were interested enough in him to engage in talks with the Blue Jays themselves even after he was dealt to Toronto. If the Blue Jays are looking to retool their offense the trade market could be the best way to do it. The Cubs would surely have interest in Soriano again this offseason, or they could roll the dice on youngster Trey Yesavage after a decent season derailed by injury.
Either way, Shaw would provide the Jays with much-needed infield help. He'd be a perfect right-handed complement to the lefty-swinging Josh Smith, creating a strong platoon that features two versatile players capable of moving around the diamond as needed. The pair could cover second base, left field, or even the hot corner on a daily basis depending on the needs of the team.
Would the Cubs loop back around to the Angels after disappointing summer trade talks?
Reports of a trade that would've sent Reid Detmers from the Angels to the Cubs ultimately broke the hearts of fans all around Chicago when they proved to be false, but there's plenty of evidence that the teams did talk about trades extensively this summer. That resulted in the deal that sent Moises Ballesteros to Anaheim in exchange for Ryan Zeferjahn. Neither of those players have made an impact for their new clubs yet, but perhaps a bigger trade could be worked out this winter.
Detmers has only upped his game since the deadline passed, with a sterling 1.65 ERA and a strikeout rate approaching 30% in his last eight starts. He's broken out this year to become the sort of legitimate ace the Cubs clearly need to anchor their pitching staff, and they should be willing to pay top dollar to acquire him this winter if he's still available.
Shaw by himself wouldn't be nearly enough to bring back Detmers at this point, but he would be an interesting starting point for the conversation. The Angels lack much of anything in terms of viable second and third base options at the moment, and they're below average against left-handed pitching this year. Shaw would help both of those issues, giving them a solid bat to slot in at either infield position who rakes against lefties.
