The Cubs know where the problem is. Pitching sits at the top of the winter to-do list, and after it helped sink a deep playoff run, Chicago has to find a way to shore it up.
Free agency is one path, even if Tarik Skubal is not expected to be part of the conversation. There will be other pitchers on the market, but if the Cubs decide those options don’t move the needle enough, trade talks could become the more interesting route. Jed Hoyer already proved at the previous trade deadline that he’s willing to keep making calls, and Chicago came away with several moves, including Kevin Gausman and Clay Holmes.
One name that has already been tied to the Cubs is Reid Detmers. The team reportedly tried to land the Los Angeles Angels pitcher at the deadline, though nothing came together. That possibility could come back around in the weeks and months ahead.
Before the Cubs can chase arms, though, they have to decide who they’re willing to move. Bruce Levine of The Score floated Matt Shaw as a possible trade chip, and it’s not hard to see why that idea has traction.
Chicago has the best defensive team in baseball, with two Gold Glove Award winners and the league lead in defensive runs saved. That kind of depth gives them some flexibility.
Levine said the New York Yankees and Seattle Mariners made the most sense as potential landing spots for Shaw. The Yankees have a clear opening at second base after the loss of Jazz Chisholm, while the Mariners could offer the Cubs the kind of pitching inventory they want to tap into.
There’s also a fresh connection between the two clubs. Seattle hired Jason Kanzler this month as its next manager, and Kanzler, the former Cubs farm director, should know exactly what Shaw brings to the table.
If Chicago is looking for a pitching target from Seattle, Logan Gilbert stands out. He’s not a top-end starter, but he does miss bats, and he’s had several 200-strikeout seasons. Adding that kind of arm would change the look of the rotation in a hurry, and moving a player like Shaw for Gilbert would qualify as a real upgrade.
None of that is meant as a slight to Shaw. He’s a reliable, versatile utility player, and Jed Hoyer said he could even compete for a corner outfield spot next season. But the Cubs need pitching now, and they may have to use the pieces they already have to get it.
Shaw hit .237 with 5 HR and 24 RBIs last season, and his role shrank from 126 games in 2025 to 77 appearances in 2026. That leaves him looking like something of an odd man out in Chicago. Keeping him as a bench piece in 2027 would be nice, but it could also be a luxury the Cubs can’t really afford.
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Philadelphia has emerged as a team to watch, but the fit is not simple. The Phillies have interest, yet their luxury-tax situation and the age of their roster make another major commitment a tricky proposition, which is part of why Arozarenas market could take some time to settle. For Seattle, the bigger question is whether the bidding climbs into territory that makes a reunion unrealistic even before the winter really gets going. [Read more 🡒]