There's only 1 free agent left the Cubs should push their chips in on

A short-term deal with annual opt-outs like the one that helped Chicago re-sign Cody Bellinger could entice this top-end free agent to join him.

Chicago Cubs Workout
Chicago Cubs Workout / Michael Reaves/GettyImages
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The general consensus throughout the league, according to USA Today's Bob Nightengale, is that free agent left-hander Jordan Montgomery will eventually wind up signing with the Boston Red Sox.

The fit is there from a roster standpoint and the fact his wife is in residency at a Boston area hospital doesn't hurt matters, either. Montgomery would add impactful depth to a questionable Red Sox rotation and give new chief baseball officer and longtime Cubs executive Craig Breslow his first major signing since joining the organization earlier this offseason.

But the fit has been there all winter long and, still, no deal has gotten done. After watching two other high-profile Scott Boras clients settle for short-term deals with annual opt-outs in Matt Chapman and Cody Bellinger, it's worth wondering if Montgomery will follow suit - which could deepen his list of potential suitors.

The Chicago Cubs are one team we know wouldn't have interest in a high-dollar, long-term deal. But were that demand to change and Jed Hoyer could bring the left-hander in on a three-year pact with opt-outs at the end of every offseason, it could make the Cubs one of the biggest winners of the offseason.

Montgomery split the 2023 season between St. Louis and Texas, playing a key role for the World Series champion Rangers in the postseason. A reunion between the two makes sense, but Texas is facing payroll limitations based on reduced TV dollars as the game's media landscape continues to shift. But it's worth noting if he started listening on short-term deals, the Rangers would almost certainly re-enter the picture as a potential landing spot.

Cubs could dramatically deepen the rotation by signing Jordan Montgomery to a short-term deal with multiple opt-outs

Slotting Montgomery in behind Justin Steele at the top of the rotation with Jameson Taillon, Kyle Hendricks and Shota Imagana behind him (and potentially Jordan Wicks, should Craig Counsell go with a six-man rotation), the Cubs' rotation would immediately get a lot deeper to open the year. Paired with a lot of top-level prospect arms knocking on the door and it's easy to see how the staff could wind up being a major strength for a team already expected to be one of the best defensive clubs in all of baseball this season.

Roster Resource and Spotrac both show the Cubs as currently under the first CBT threshold, but not by much. Either way, if ownership is trying to avoid going over, it seems like Hoyer would have to pair a Montgomery signing with a trade of someone like Drew Smyly and probably some other salary dumps to try and offset the added dollars.

Chicago's rotation has potential. There's no doubt about that. But adding Montgomery, who has been as consistent as they come in the last three years, would help raise the floor of the group and give Craig Counsell another dependable arm to turn to every five days,

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