More Info on Cubs’ Pitching Pursuits of Yamamoto, Cease, Glasnow, Montgomery

I’ve already milked Jeff Passan’s Winter Meetings preview for two other posts, so might as well take one more tug at the teat before calling it a day. This will be somewhat brief, or at least that’s the hope, because there’s not much meat on this bone after having gnawed on it for a few days already. With that in mind, let’s start with the biggest name.

Yoshinobu Yamamoto is one of the most sought-after free-agent pitchers ever, and I’m not just talking about Japanese imports. His youth and skillset have created an incredibly robust market in spite of a price tag expected to exceed $200 million because even rebuilding teams can try to sell eventual competitiveness. He’ll whittle down the field and will then hold in-person meetings with the finalists after the Winter Meetings, with a decision expected well ahead of his posting window closing on January 4.

Passan listed the Cubs among a group of favorites that includes the Yankees, Mets, Dodgers, and Red Sox, with the Blue Jays, Giants, and Phillies also in the mix. Yamamoto is said to prefer a major market, though that might be subject to the same sort of misinterpretation that led to rampant reporting that he wanted to join a team that already had a Japanese star in place. I guess we’ll find out once those meetings begin.

As much as I’d like to see Yamamoto on the North Side, I’m not very bullish on the Cubs landing him. If they don’t, it’s possible they could pivot quickly lefty Jordan Montgomery. After noting that Montgomery could be a “strike-first option” for the Red Sox if they don’t feel they’re getting Yamamoto, Passan says the same is true for the Cubs. Montgomery should cost significantly less than his Japanese counterpart and he’d shore up a rotation that probably needs two total additions.

The Cubs have been among the most oft-mentioned teams involved in talks with the Rays for Tyler Glasnow, something that has been confirmed over and over again in the last few days. A tag-teamed report from Bleacher Nation’s Michael Cerami, Fantrax’s Michael Marino, and Jack Azoulay-Haron of MLB Nerds named the Cubs once again in a group of 3-5 teams showing interest in the lanky righty.

Passan also mentioned the Cubs as a team with the desire for starting pitching and the ability to put together a package that could reunite them with former farmhand Dylan Cease. It’s not often you see a team trade for a player they’ve previously dealt away, mainly because the prospect of a bruised ego can be more of a deterrent than the pain of losing prospects.

Cease is projected to earn around $9 million through arbitration next season and less than $20 in his final year of control, making him cheaper and more reliable than Glasnow. Even though there isn’t nearly as much of a stigma surrounding crosstown swaps these days, something Cease has been a part of already, it feels like other teams might be more willing and able to make something happen here.

I’ve been saying for a while now that it makes sense for the Cubs to add two starters, one each via trade and free agency. They need a little more long-term security from the latter because Marcus Stroman is gone and Kyle Hendricks is only under contract for one more season. That allows them to make a riskier trade for someone like Glasnow since his limited control keeps them flexible next season.

Whether you want to look at that as creating room for Cade Horton or just carrying the load for Shohei Ohtani in 2024, it makes sense. The Cubs have a good chunk of money falling off the books at the end of the 2024 season and again after 2026, so they can spend big this winter and even enter competitive balance tax penalty territory knowing they’ll be able to get relief in future seasons.

As such, it’s not out of the question to think about them taking on multiple high-AAV contracts even if the reality of signing Ohtani, Yamamoto, and [enter third big deal here] isn’t entirely likely. With a current projection of around $186 million in CBT payroll, the Cubs are approximately $51 million below the first CBT threshold and appear to be displaying a willingness to blow through it. The next level at $257 million might also be seen as a small hurdle, though approaching the second penalty line of $277 million is incredibly unlikely.

The whole thing is pretty malleable, though, since actually getting both Ohtani and Yamamoto would allow ownership to tap additional revenue streams. That’s why you’re seeing the Cubs connected to so many top free agents and trade targets. It’s not a matter of the team trying to get one over on the fans, it’s because Jed Hoyer can’t just laser focus on one or two players and be left holding his dick in his hand if those pursuits don’t pan out.

There’s a sense that the Winter Meetings will bring a lot of activity, though that’s been less the case over the past few years. Ah, but Ohtani and Yamamoto making decisions by mid-December would serve as catalysts to get the market moving in a big way. I’d say by this time next week, we’ll be able to discuss actual moves rather than speculation.

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