With the exception of not having too many holes to fill around the diamond, the Chicago Cubs have PLENTY of reasons to spend big in free agency this winter.
After all, they’re a good team that just finished a competitive season (fueled mostly by young players), with plenty of payroll space already available (and even more coming off the books in 2026). Yes, the CBA persists as an existential/strategic hurdle, but that’s not specific to the North Side of Chicago. So again, relative to everyone else, there’s no reason for them not to ball out in free agency. And yet …
Who seriously believes that’s what they’ll do?
Bob Nightengale, that’s who!
Earlier this morning at USA Today, MLB Insider Bob Nightengale suggested that our beloved Chicago Cubs could be “the hot stove’s biggest sleeper” this offseason, filling in the details thusly:
The Chicago Cubs know that finishing second to the Milwaukee Brewers in the NL Central every year is inexcusable, and with Tucker expected to depart for greater riches, they’ll have plenty of money to burn. They want another corner outfielder, and will be shopping in the expensive aisle for starting pitching, with fellow GMs predicting they could land Framber Valdez and/or Dylan Cease.
Oooookay, then. For a two-sentence opinion, there’s actually a lot to dissect there. But I want to first respond to the broader characterization about them being the biggest sleeper. Because, frankly, I don’t buy it. Or, at least, I won’t be selling that to you. Not this winter. Not again.
Remember, these Cubs didn’t “go big” after swooping in and signing Craig Counsell to the largest contract in MLB managerial history. They didn’t “swim in the deep end” after trading away a ton of prospect and player capital for one year of Kyle Tucker. And they didn’t “go all in” at the most recent trade deadline, when they were in a clear window of contention with glaring needs in the rotation/pen.
You can debate the merits of each decision in retrospect all you want. But at the time, it was easy to make a case for doing more. And they never did, because they almost never do.
Thus, I have adjusted my expectations accordingly, and you should too. For whatever reason, the Jed Hoyer-run (and Tom Ricketts-funded) Chicago Cubs do not seem to meet the payroll expectations of the industry. And I’m sick of looking foolish in anticipation of something different.
But now that we’ve cleared our throat, let’s look a little closer. Some of it is believable, some is less so, and some of it is downright confusing.
In terms of the “believable,” there’s the Dylan Cease mention. For however much we do not expect the Cubs to spend big in free agency (because they rarely do, especially for pitching), Dylan Cease does fit the mold of the TYPE of pitcher they probably would like to target (hard-throwing, strike-getting, right-handers). They also drafted Cease, themselves, all those years ago, and have been connected to him in free agency earlier this winter.
***REPORT: Cubs Expected to Pursue Free Agent Starter Dylan Cease This Winter***
Given where his initial contract projections have landed, I still think it’s a long shot, but Nightengale is hardly alone in making this connection between the Cubs and Dylan Cease. Anyway, that’s the believable part.
© David Frerker-Imagn ImagesSimilarly, but less believable, is another Cubs/Framber Valdez mention. Once again, Nightengale isn’t the only one who’s tied these two together. And I do love the idea of putting a guy with a career 61.8% groundball rate in front of the excellent Cubs’ infield defense. But his price tag could be even higher than Cease. Combine that with the fact that he’s a short, left-handed, older pitcher who doesn’t throw hard … and I just stretch to believe that’s going to happen.
It’s not crazy, and it’s not a bad idea. But it’s just not a line I’m buying. And I am *certainly* not going to dwell on Nightengale’s use of “and/or” as if there’s any shot the Cubs would try to sign both.
Lastly, and most confusingly, is their reported interest in adding another corner outfielder.
Remember, Seiya Suzuki and Ian Happ have no trade clauses — clauses that are unlikely to be waived. Pete Crow-Armstrong is starting every game in center field, no matter what (and is not a corner outfield factor anyway). Owen Caissie is around to play right field when Suzuki isn’t, and Moises Ballesteros is around to DH … also when Suzuki isn’t.
I tend to think, then, that this rumored interest was just a half-baked acknowledgement that the Cubs are losing a corner outfielder in Kyle Tucker.
Losing Tucker is going to sting, and they do need to add something significant to the offense to offset his loss (minus whatever you might get from Owen Caissie and Moises Ballesteros), but I just don’t think that addition is going to come from the corner outfield market.
Maybe things change if Caissie and/or Ballesteros are traded for starting pitching. Or maybe there’s an unexpected trade candidate out there (like Tucker last season) that changes everything. But that’s a lot of moving parts/ifs. So I wouldn’t count on that. And I’m just going to park this in the back of my brain for the time being.
***
So, then, am I happy to hear Nightengale suggest that the Cubs might be getting busy this winter? Sure. But only in that it’s better than him HEARING definitively that they won’t. There are plenty of good players available, and plenty more reasons to get aggressive … But we’ve been burned by this line of thinking way too many times in the past. So this time, I’ll believe it when I see it.
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