The Cubs have not yet made any sort of major free agent signing or trade acquisition this offseason. In fact, the Winter Meetings were pretty quiet on the transaction front, with the exceptions of the signings
of Pete Alonso, Robert Suarez and Edwin Diaz, all by teams other than the Cubs.
This, you already know.
Today, I am going to ask you what you think Cubs President of Baseball Operations Jed Hoyer and his team should prioritize next.
Starting pitching
As things stand right now, the Cubs rotation is Matthew Boyd, Cade Horton, Shōta Imanaga, Colin Rea and Jameson Taillon, with Javier Assad, Ben Brown and Justin Steele (whenever he returns from Tommy John surgery) as the next three options. (I listed the first five in alphabetical order, not any sort of priority order.)
Over the course of this offseason I’ve posted quite a number of free agent and trade possibilities for the Cubs. You can certainly find those articles by searching this site. Of the top free agent pitchers, only Dylan Cease has signed. The rest are still out there.
Should they sign or trade for one of those guys as a top priority?
Relief pitching
The Cubs have been reported to have signed left-hander Hoby Milner, though the team has not yet made that signing official. They also signed right-hander Phil Maton to a two-year deal.
Those are both good signings for this bullpen, I think. But the Cubs are likely far from done, as 2025 bullpen stalwarts Brad Keller, Caleb Thielbar and Drew Pomeranz are all free agents.
Milner likely replaces one of the two left-handers. Personally, I’d like to see the Cubs bring back Keller and Pomeranz.
Where else should they look for relief help?
Third base
The Cubs pursued Alex Bregman last offseason, but were outbid by the Red Sox. There were recent reports that the Cubs were still interested after Bregman opted out of his Boston deal. From all the things I have heard, the Tigers and Cubs are the two teams most in pursuit of Bregman.
If the Cubs do sign Bregman, that leaves them with two choices for Matt Shaw.
- Make him into a kind of super-utility guy
- Trade him
Personally? I’d trade Shaw. He’s got significant trade value and could be part of a deal to bring a good starting pitcher to the Cubs, perhaps even someone with multiple years of team control.
Or maybe you think there’s another thing that’s more important to the Cubs right now.
Have at it.
