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

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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

Chances of the Cubs signing these free agents: Blake Snell - Low

I mentioned Blake Snell as somebody the Cubs should go after earlier in the offseason. My feelings haven’t changed much, except for the part where I don’t think they will. Fresh off his second Cy Young season, Snell has put up good numbers in the last four seasons. His best, obviously, came in 2018 when he recorded a 1.89 ERA, going 21-5. Since 2020, he’s managed a respectable 3.16 ERA, along with an 11.8 K/9.

I only see Snell falling to Chicago if Jed Hoyer entices him enough with a short-term, high AAV deal. It doesn’t seem realistic for Snell to sign a two-year deal. He wants to be locked in and make money now and deserves to. Unless the front office can get him down to three years, I don’t see Hoyer willing to do much more.

Given how the market is, Snell will probably wind up with a four or five-year deal, and teams will drive up the AAV to a level Hoyer just isn't going to bite at. Snell has said he prefers to play on the West Coast, but the Dodgers have little interest here. The Angels and Giants seem like potential landing spots - as both need to add some impact pitching.

Prediction: San Francisco Giants

The odds of players landing in Chicago: Shota Imanaga - Medium

Shota Imanaga is more viable as a Cubs target than the two pitchers I just mentioned. His expected contract aligns more with what Chicago would likely be comfortable spending, but some issues come with that price tag. For one, the Cubs aren’t going to blow past the luxury tax this season. Landing and dedicating $20 million annually to Imanaga means he’s the only starter you’re getting if you plan to bring back Cody Bellinger and sign Rhys Hoskins.

Chicago remains interested in a reunion with Bellinger - but not at his reported asking price - and Hoskins makes about as much sense for the Cubs as any free agent out there given their need at first. But Imanaga would lengthen the rotation and, hopefully, give Justin Steele some help after his breakout season in 2022.

But there's a decent chance that once Snell and Montgomery come off the board, a bidding war could drive up Imanaga's price, as well. The Cubs might be forced to look to the trade market if they don't lock up one of the remaining free agent starters soon.

Prediction: Boston Red Sox

Chances of the Cubs signing these free agents: Cody Bellinger - Medium to high

Let’s address the elephant in the room. We know what Cody Bellinger did in 2023, the red flags of his barrel rates and all the stuff we won’t re-hash here. The fact is, the Bellinger market is already disintegrating after teams made their moves. The Dodgers have Ohtani, the Yankees added Soto, the Mets aren’t in the market, the Giants added Jung Hoo Lee, etc. It appears this is down to the Cubs and Blue Jays.

The Blue Jays' hot pursuit of Ohtani worries me. They are willing to spend big this season. Does that mean they will drastically overpay for Bellinger? He had some very down years, followed by a remarkable comeback season on a contract year. You can bet he will have solid upside and overall sound production for you, but you can’t call him a perennial MVP candidate at this point.

If the Blue Jays ridiculously overpay for him, which shouldn’t be considered out of the realm of possibility with their clock ticking, then so be it. If they don’t, the Cubs will be in the bidding once the price comes down, where they should have the edge to bring him home.

Prediction: Chicago Cubs

Chances of the Cubs signing these free agents: Rhys Hoskins - High

Rhys Hoskins has been linked to the Cubs all winter. But with Scott Boras holding all the cards (he's the agent for not only Hoskins, but also Bellinger) - things have been slow to play out. Given the amount of needs this team has, Chicago isn't about to overpay, especially for a guy coming off an injury - regardless of how good a fit he may be.

Hoskins was a longtime staple in Philadelphia before a knee injury cost him his entire 2023 season. Now, looking to re-establish himself as a quality power bat, the Cubs could give him the same platform they offered Bellinger in 2023 - a short-term 'prove it' deal that could allow him to hit free agency again soon.

After the disastrous Eric Hosmer and Trey Mancini signings from a year ago, Hoskins should bring a relative degree of certainty at first - and he likely won't break the back, allowing Chicago to address the pitching staff and, hopefully, make a run at bringing back Bellinger, too. There's been so much smoke here that it's hard to believe the two sides don't get a deal done.

Prediction: Chicago Cubs

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