There’s still over a month until pitchers and catchers report to spring training. There’s still a dizzying array of talent available via free agency or trade, from Kyle Tucker to Bo Bichette to Alex Bregman to Framber Valdez to Freddy Peralta. This offseason is far from set in stone, and any team at any time could vault themselves into the contender conversation. (Well, OK, maybe not the Rockies.)
And yet, what’s done is done. We haven’t gotten a ton of action so far this winter, but what we’ve seen so far has had some highs … and some real head-scratching lows. Below are eight decisions, or non-decisions, that teams and fan bases are going to be regretting for years to come.
The Tigers resigning themselves to losing Tarik Skubal
Division Series – Detroit Tigers v Seattle Mariners – Game 5 | Jane Gershovich/GettyImages
It would be one thing if Skubal simply had his sights set on an astronomical contract that only the Dodgers could touch, or had no interest in spending the rest of his career in Detroit. But the Tigers don’t seem to have even forced their two-time Cy Young winner to make that choice. Instead, they’ve just meekly accepted their fate before it even happens — not trading Skubal (because really, there’s no package in the world that would convince a contending team to move arguably the best pitcher on the planet) but also not seriously pursuing a contract extension.
Heck, they’re not even trying to load up for an all-in push in 2026. Scott Harris continues to act like the Rays of the AL Central, as if spending a little money or getting a little out of his comfort zone might set his organization back a decade. But the reality is that he’s going to watch this window of contention pass him by because he’s scared of his own shadow. Tigers fans deserve better
The Cubs not being in on Tatsuya Imai
Houston Astros Introduce Tatsuya Imai | Houston Astros/GettyImages
If you want to focus on Chicago’s preemptive abandonment of the Kyle Tucker sweepstakes, be my guest; there’s zero reason why this franchise in this market shouldn’t be in the running to keep a star player it acquired last offseason. But maybe Tucker’s asking price remains north of $400 million, and the Cubs don’t want to let that hijack the rest of their winter. Fair enough.
What about the rest of the roster, though? This lineup is built to contend, and yet Jed Hoyer has done woefully little to bolster a pitching staff that simply wasn’t good enough down the stretch last year. The Cubs are crying out for one more impact starter, the kind of guy you feel good about giving the ball to in October. Even if you don’t want to pay up for someone like Dylan Cease and Framber Valdez, Imai felt like a great compromise, an upside arm who wound up signing an exceedingly reasonable deal with the Astros. Chicago isn’t in the position to let opportunities like that pass it by, and if Imai becomes a No. 2 or No. 3 starter, it’s really going to sting.
Hal Steinbrenner handing the Yankees a very clear budget
Division Series – Milwaukee Brewers v Chicago Cubs – Game Four | Matt Dirksen/GettyImages
No team better embodies the glacial pace of this offseason so far than the New York Yankees, who saw Trent Grisham accept his qualifying offer in November and then … and have pretty much sat on their hands in the weeks since. Given the urgency involved in capitalizing on what’s left of Aaron Judge and Gerrit Cole’s primes, it seems hard to believe that Brian Cashman would be so complacent about a roster that got exposed in the ALDS last season.
The much more likely scenario is that Hal Steinbrenner, after months of bellyaching about how it’s unfair that he has to spend so much money on his baseball team, gave Cashman a tight budget within which to work. Look no further than New York’s outfield: Kyle Tucker would seem in every respect to be a perfect fit, a middle-of-the-order bat to give Judge some protection and finally stabilize left field. But instead, the Yankees have been totally absent from the Tucker sweepstakes, instead waiting around for Cody Bellinger — a good player, but with a much lower ceiling and a much sketchier track record — to fall into their laps.
Maybe Steinbrenner will prove us all wrong. Maybe a big splash is right around the corner, one that will prove he’s serious about keeping pace with the big boys. Right now, though, it sure seems like he’s more concerned with fiscal responsbility than anything else, and his team is about to pay the price.
The Rangers willingly acquiring Brandon Nimmo (and his contract)
New York Mets v Miami Marlins | Megan Briggs/GettyImages
I get the idea, in theory. Texas needed some outfield help, and ownership’s belt-tightening forced Chris Young and this front office to try and address current needs without increasing payroll. Nimmo’s been a good player for a long time, he fills a need and his contract comes with a lower AAV than Marcus Semien’s.
But in trying to play four-dimensional chess, the Rangers may have locked themselves into an even uglier long-term situation — all without meaningfully changing their 2026 outlook. Nimmo is set to make $20 million a year through 2030, a harrowing thought for a guy who’s about to turn 33 and has already seen his athleticism start to fall off a cliff. The version of Nimmo who could play a solid center field with a 120 OPS+ is well worth that salary. But Texas could also be getting a version who’s a roughly league-average bat who’s barely hanging on in a corner, and that’s an albatross.
The Angels betting on Grayson Rodriguez
Toronto Blue Jays v Baltimore Orioles | Diamond Images/GettyImages
Not too long ago, Rodriguez looked like a budding star, a former first-round pick and star prospect who broke out in a big way in a successful 2024 season. For an Angels organization that’s struggled to develop their own starting pitching for years now, why wouldn’t you buy low on a guy like that — especially when all it costs is Taylor Ward, a free agent next winter who doesn’t factor into your future plans?
Well, because Rodriguez unfortunately might be cooked. After missing the end of 2024 due to a shoulder issue, his 2025 season was derailed before it even got going: first came elbow inflammation in spring training, and then a shoulder strain, and finally season-ending elbow surgery. The last time we actually saw Rodriguez on the mound, he looked like a shell of himself, sitting in the low 90s with his fastball. Los Angeles (and Rodriguez himself) swear he’s healthy and that his medicals came back clean. But I have less than zero trust in his arm moving forward, especially considering the Angels’ track record.
The Reds sitting on their hands
Division Series – Philadelphia Phillies v Los Angeles Dodgers – Game Three | Ronald Martinez/GettyImages
No one can be too hard on Cincinnati for falling short in the Kyle Schwarber sweepstakes. Signs always pointed toward a reunion in Philly, and the Phils showed exactly how much they valued him by paying up to the tune of $155 million over five years — a massive amount for a 32-year-old DH.
The real problem has been everything the Reds have done since. Or, more accurately, haven’t done: Despite a rotation ready to win big, and a lineup in desperate need of some punch, Cincy’s front office has more or less sat on its hands, fiddling around the margins while plenty of viable options fly off the board. Even if you want to make the usual small-market excuses, why wasn’t this team in on Ryan O’Hearn, or Kazuma Okamoto, or even Jorge Polanco? Do the Reds have any interest in competing next year, or are they content to cash a revenue-sharing check and throw up their hands the next time they get boatraced by the Dodgers?
The Orioles trading the farm for Shane Baz
Tampa Bay Rays v Chicago Cubs | Michael Reaves/GettyImages
I know the Orioles needed to find starting pitching this offseason. I know that Baltimore has been begging Mike Elias to finally get aggressive in adding Major League talent. I know that Baz, still just 26, could put it all together and become a top of the rotation guy.
But man … that’s a lot to give up for a player long on potential and short on actual results. Outfield prospect Slater de Brun, in particular, was a huge get for Tampa, and that was just one of four meaningful prospects the Rays received in return — plus a competitive balance pick in next year’s draft. Baz has an explosive right arm, but he pitched to a 4.87 ERA last season, and not all of that can be blamed on his miserable home park. Add in his injury history, and the other options out there to be had, and I’m not sure the value adds up here.
The Dylan Cease contract
Milwaukee Brewers v San Diego Padres | Sean M. Haffey/GettyImages
I almost feel badly including this one, both because I respect the hell out of Toronto’s offseason aggression after falling two outs short of a World Series and because I think that Cease represents a smart bounce-back bet in the near term. But man: $210 million over seven years is a big price tag, and the Jays better hope they’re able to pay it off with a commissioner’s trophy in the next year or two.
Cease brings innings and strikeouts in bundles, but both of those things figure to taper off as the 30-year-old ages and his stuff begins to decline. Which is a problem, because without good command to fall back on, this profile could get very ugly. For 2026, I have no problem paying Cease top dollar. For his ages 34, 35 and 36 seasons, though? Yikes.