Cubs May Be In On Williams & I'm Good With That

I’ll be honest: Devin Williams to the Yankees always felt like inviting a raccoon into your kitchen because “maybe it’ll cook.” Unnecessary chaos. A vibes sinkhole. A self-inflicted wound we absolutely did not need going into 2025.

The Yankees would have been perfectly fine rolling with the bullpen they had and making adjustments on the fly—shocking concept, I know. Instead, Brian Cashman decided to get cute and shipped off Caleb Durbin, a major-league-ready infielder who could’ve actually helped the Yankees in the spot they desperately needed help. And what did we get? A season of infield musical chairs, a bullpen that felt like a panic attack in real time, and Devin Williams… existing.

Honestly, I didn’t want him here. Still don’t.

But—maybe—the winds are shifting. The Athletic says the Cubs are rethinking how they build bullpens this winter, which is a polite way of saying: “We realized one-year deals for relievers is the baseball equivalent of duct-taping a broken chair.” They might even commit to multi-year deals for the right late-inning arms. No, not Edwin Díaz money, but real investment.

Naturally, Devin Williams—Counsell’s old Brewers closer—is on their radar, and apparently drawing enough interest that his next contract might stretch beyond what the Cubs are even comfortable with. They’re also sniffing around Pete Fairbanks. In other words: Chicago might actually give Counsell options instead of prayer candles.

So… what does that mean for the Yankees?

Simple: if Devin Williams packs up his changeup and leaves the Bronx, I will personally throw a parade. Streamers, confetti, the whole thing.

And let’s not pretend this saga hasn’t been a mess. Williams went through a full-blown confidence crisis this season and admitted it out loud after coughing up a loss to the Astros: “I stink right now.” He said he hasn’t felt like himself, hasn’t found his groove since Tommy John, and is basically fighting ghosts out there. This is not the energy you want anchoring your bullpen.

He’s a free agent after 2025, and of course Brian Cashman—king of familiarity hires and emperor of the “easy way out”—might try to bring him back. Why? Because it’s simple. Comfortable. Familiar. It’s classic Cashman: miss the big picture entirely, then pretend he’s playing 4-D chess while the rest of us are watching him knock over his own pieces.

Letting Williams walk would be the smartest thing the Yankees could do. His shaky performances made the bullpen wobbly, his beard policy drama created noise for no reason, and the whole thing even threw Luke Weaver out of sync. Domino effect chaos.

And sure, the Mets, Cubs, Dodgers, and Giants are reportedly interested in Williams. He’ll get his market. Some team will gamble on a bounce-back. Good for them.

Me? I’m praying the Yankees sleep through the entire bidding process. If Craig Counsell truly feels comfy cozy with Williams, then by all means—Chicago, come get your guy.

One less bullpen headache in the Bronx? Yes, please.