Cubs Still Have Walker Buehler on Radar, Rising SP Prices Make Trade(s) More Likely

The pitching market has exploded this offseason, with Clay Holmes‘ three-year, $38 million deal serving as the latest example. He’s a guy I expected the Cubs to be after as a late-inning reliever, but the Mets plan to have him transition to the rotation and are overpaying as a result. There’s also a sense that Rōki Sasaki has already chosen a team even though he won’t be posted until the Winter Meetings, so not many execs are waiting on him before looking elsewhere.

Even if Sasaki’s courtship is truly open, his low salary and the fact that international signing bonuses don’t count toward luxury tax calculations means anyone could easily add him and another starter. As an aside, I want to clear something up on the signing bonus front because I’ve seen some erroneous information out there. Signing bonuses for big league free agents do count toward the AAV of their contract.

Anyway, the Cubs remain interested in adding another starter after officially announcing the signing of lefty Matthew Boyd on Saturday. A trade seems to be the most likely means by which to do that since they have tradable assets and can get a relative bargain over what they’d have to pay on the open market. Sahadev Sharma and Patrick Mooney reported that Walker Buehler remains on the radar as well, though his postseason performance could well push him outside the range of Jed Hoyer’s value matrix.

Javier Assad appears to be the odd man out if the Cubs are able to add another starter, though they seemed to be toying with the idea of a six-man rotation for a while last winter. GM Carter Hawkins shot that down just prior to spring training, saying they considered “all the different permutations” before opting for a more traditional structure. Considering Boyd hasn’t made more than 15 starts since 2019, it would be wise to at least revisit the idea of rolling with at least a modified starting unit.

I like Buehler quite a bit and would be happy to see the Cubs land him on a one-year pillow deal similar to what Shane Bieber — who had been my preference — inked to return to the Guardians. The former Cy Young winner will earn $10 million in 2025 and has a $16 million player option for 2026 that carries a $4 million buyout. That’s reportedly less than offers he had from other teams and Bieber may not even be ready to pitch in the first half, so it’s reasonable to expect Buehler to exceed those figures.

Of all the different deals being thrown around lately, I think I like the hypothetical trade that would send Cody Bellinger to Seattle for former Reds ace Luis Castillo. That would significantly raise the rotation’s floor and give them an experienced veteran who’s under control through 2027 with a vesting option for ’28 that kicks in if he logs 180 innings in what would otherwise be the last year of the deal. And since Castillo is a righty, the Cubs could still trade for Garrett Crochet and have a perfectly balanced six-man rotation.

That’s probably way too much to ask for, but it would mitigate the need to add as much to the offense from external sources. I’m sold on Pete Crow-Armstrong‘s continued development as a hitter, though, and I believe Matt Shaw will be the goods. Throw in a decent rookie campaign from Owen Caissie and just a little more consistency from Dansby Swanson and Ian Happ, and you’ve got the makings of a very strong team.

One thing I’ve seen mentioned quite often that I want no part of is signing Pete Alonso to play first base/DH. As much as the Cubs could use that thump in the lineup, I’m not sold on the Polar Bear’s ability to be much more than a 2-3 WAR player with diminishing returns over the life of what figures to be a contract in the five-year, $125 million range. Michael Busch is a better defender and should be able to bang out 25-ish homers at a fraction of that cost.

Don’t mistake that for me urging the Cubs not to spend, I just don’t think it’s wise to pay literally 25 times as much for a dude who might give you 5-10 more homers and potentially lower overall impact. Wait, wasn’t this supposed to be about pitchers?

Yes, yes it was. I’m confident saying the Cubs will land another starter and that it’ll most likely come via trade, then it’s a matter of retooling the roster to give a couple of their top prospects a shot to break camp with the big club. From that point, they’ll have to rely on coaching and development changes to foster an environment in which players can exceed expectations.