Simply put, the Chicago Cubs need to add pitching this offseason. It's their biggest weakness after playing a big part in costing them a deep playoff run. Fixing it will not be easy, but they can do so in multiple ways this winter.

To be sure, the team is not expected to pursue top free agent Tarik Skubal, but many other capable free-agent pitchers will be available. If the Cubs aren't in love with those options, however, they could also look to acquire talent through trade. Jed Hoyer showed that he isn't afraid to make calls at this previous trade deadline. They pulled off several moves, which included the addition of Kevin Gausman and Clay Holmes.

The Cubs, by all accounts, also attempted to add Los Angeles Angels pitcher Reid Detmers at the trade deadline, but nothing transpired. Is that something they could revisit in the coming weeks and months?

Well, before we even think about who the team might target, we might as well consider who they would try to send out in a deal. And Bruce Levine of The Score pointed out a trade candidate who could help them improve their pitching.

Matt Shaw Can Help the Cubs Improve Their Pitching Depth

The Chicago Cubs have the best defensive team in baseball. They have two Gold Glove Award winners, leading the league in defensive runs saved. With such stellar defense, why not trade away some of their depth to improve the pitching?

Bruce Levine mentioned that trading Matt Shaw could be a viable option for the Cubs. The teams that made the most sense to him were the New York Yankees and the Seattle Mariners. Although the Yankees have some great options and have a huge need at second base due to the loss of Jazz Chisholm, the Seattle Mariners have a boatload of arms that the Cubs would love to bring in.

There is also no ignoring the new connection between the Cubs and Mariners. This month, Seattle somewhat shockingly hired Jason Kanzler to be their next manager. The former Farm Director for the Cubs, he is going to be well aware of what a player like Shaw can offer them.

As for who the Cubs should target on their pitching staff, Logan Gilbert arguably stands out the most. He’s not a top-end starter, but he’s an arm who will get you plenty of strikeouts. Gilbert has had several 200-strikeout seasons. It would improve the rotation drastically. Swapping a player like Shaw for someone of Gilbert's caliber would be considered an upgrade. 

It’s not a knock on Shaw, to be clear. He is a reliable and versatile utility player. President Jed Hoyer even said he could compete for a corner outfield spot next season. But the Cubs need to add pitching as fast as they can. Now is the time to use the tools you have to upgrade the team.

Last season, Shaw hit .237, had 5 HR, and only 24 RBIs. He dropped significantly, going from 126 games in 2025 to only 77 appearances in 2026. It's clear that he's a bit of an odd man out in Chicago right now. Would having Shaw back on the bench in 2027 be helpful? Sure, but it might also be considered a luxury the Cubs can't afford.