The Chicago Cubs missed on Devin Williams despite his interest, which underscores a front office still too cautious to land the players it needs most.
The Winter Meetings have come and gone, and the Chicago Cubs still don’t have their big-fish free-agent addition.
Kyle Schwarber signed a five-year, $150 million contract to return to the Philadelphia Phillies. The Cubs never felt like serious suitors in that sweepstakes. And the writing has been on the wall for Kyle Tucker for quite some time now — he won’t be back on the North Side.
Cubs fans even got teased by a fake report claiming the team had agreed to terms with starting pitcher Zac Gallen. That would’ve generated real buzz had it been true, but that deal isn’t anywhere close. And despite assurances from president of baseball operations Jed Hoyer that upgrading the rotation was a priority, the Cubs have yet to add a single starting arm.
Even the bullpen needs help — a lot of help. Daniel Palencia is a fine closer, but Chicago is completely lacking other lightning-rod, high-leverage options.
Signing Devin Williams would’ve made all the sense in the world. He has closed in the past, but he’s also been one of the most dominant setup men in baseball dating back to his time with the Milwaukee Brewers — and Cubs fans know that well. The Cubs did pursue Williams, but they fell into what’s becoming an unfortunate habit: refusing to outbid the rest of the market and coming up short.
According to Bruce Levine, Williams wanted to sign with the Cubs over the Mets… but Chicago didn’t make an offer that competed with the $51 million he got from New York.
I’m sure it felt like an overpay for Chicago. Welcome to free agency. At this stage of the offseason, the only way to actually get deals done is to overpay slightly beyond what seems rational.
Teams like the Los Angeles Dodgers — or in this case, the New York Mets — are always willing to give the extra year or the extra chunk of change. That’s why they consistently land big-name free agents while Chicago’s involvement is an afterthought in the aftermath.
And that’s the problem with the Cubs that outsiders can’t seem to comprehend.
Yes, the organization spends. Yes, they regularly operate with a payroll in the top half of baseball. They don’t recoil at the thought of a nine-figure deal. “Smart money” is a great philosophy in the early stages of a build. But it becomes an Achilles’ heel when it’s time to win.
If they won’t make a competitive offer for Williams — who checks every box in an area Hoyer himself identified as a priority — then what are they willing to overpay for?
A third baseman? Maybe not, given how loudly they’ve expressed confidence in Matt Shaw.
A frontline starter? They’d love one, but they already have five serviceable arms if they don’t want to push the market and pay true ace prices.
So yes — the Williams report should concern people.
If Chicago keeps this up during trade negotiations the rest of the offseason, Opening Day is going to arrive with the Cubs roster looking no better than it did in 2025. A playoff team? Sure. The Cubs could probably roll out their current group and land a Wild Card spot.
A World Series contender? Not a chance.