Pegging the probabilities of these 5 free agents signing with the Cubs

Yet to make a major roster move, the Cubs still have a chance to make impactful additions to the roster as we head into 2024.

Chicago Cubs v Atlanta Braves
Chicago Cubs v Atlanta Braves / Kevin C. Cox/GettyImages
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Just because the Chicago Cubs didn’t go out and spend over $1 billion between two players this winter doesn’t mean this is a lost offseason - at least not yet. As things stand, multiple high-spending teams have filled primary needs already. The Los Angeles Dodgers went crazy by adding Shohei Ohtani, Yoshinobu Yamamoto and Tyler Glasnow. The New York Yankees got their power bat in Juan Soto. Meanwhile, the New York Mets have opted to fall back after missing on their primary targets.

That means the Chicago Cubs have a chance to strike coming out of the holidays. Teams still need pitching, to be sure, but there’s still a lot of talent available. It's the same for the hitters. It’s not as if the Cubs are the only team still shopping, but it bodes well that they have a solid core in place, and the names still available are enough to propel them back to the postseason. With that being said, what are the odds that these five free agents will wind up in Chicago?

Chances of the Cubs signing these free agents: Jordan Montgomery - Low

Jordan Montgomery, rumored Cubs target, will play in pinstripes next season—unfortunately, not the blue kind. The Yankees still want to add a starter, and unlike their crosstown rival Mets, they still plan on doing so after missing on Yamamoto. Michael King proved in nine starts this year that he can be a viable starter and fill a bulk relief role when needed. After losing him in the Juan Soto deal, the Yankees will need to replace his 2.60 ERA combined over the last two seasons and fill another hole in the rotation after losing Domingo German and Luis Severino to free agency.

A reunion with Montgomery, who spent his first five-and-a-half seasons with the Yankees, makes sense for the club. Since leaving, Montgomery has posted solid numbers and, at the very least, has middle-of-the-rotation stuff. Pairing him with Gerrit Cole, after adding Juan Soto to that offense, gives the Yankees a realistic shot of climbing back up the AL East standings. While the Cubs may have interest in Montgomery, it feels like Brian Cashman will flex his financial muscle on this one, pushing the Cubs to a place where they're uncomfortable.

If Montgomery can't find an agreement with the Yankees, another viable team that seems to have a better chance of landing Montgomery than Chicago is the Texas Rangers. After winning a World Series in Texas, the Rangers are still in go mode, and Montgomery's numbers in the second half while there make him valuable. With Jacob deGrom returning before at some point, the Rangers' rotation could use the insurance and stability Montgomery can provide.

Prediction: Texas Rangers