We don't want to stick a fork in the MLB offseason just yet; it took until the middle of February for both Pete Alonso and Alex Bregman to sign last winter, after all, and there are still some interesting names left on the free agent market (and some very interesting trade rumors kicking around).
And yet, for executives around the league, the clock is very much ticking: Pitchers and catchers report to Spring Training this week, and teams are running out of time to make meaningful upgrades to their rosters before the season begins. For some World Series contenders, like the Los Angeles Dodgers, they're work is already just about done. But for others, the winter has seemingly come and gone without the necessary additions — and these front-office executives could be getting pink slips as a result.
Brian Cashman, New York Yankees
No matter how doggedly Cashman insists to the contrary, it sure seems like he and the Yankees are running back last year's team. Granted, that's not the pejorative that many fans seem to think it is: This was a really good team in 2025, winning 94 games and posting the second-best run differential in baseball. But it was also a team with flaws that got exposed against the Toronto Blue Jays in the ALDS.
I'm not sure those flaws have been addressed this offseason. The bullpen has even less depth now than it did a few months ago, with Devin Williams and Luke Weaver bolting to the cross-town Mets, while the starting rotation has plenty of big names but no guarantees that any of Gerrit Cole, Carlos Rodon, Max Fried, Clarke Schmidt or even Cam Schlittler (coming off a career high in innings) will make it to October healthy. For a team whose lack of pitching depth got exposed in October, that's a scary thought — without a Kyle Tucker-level upgrade to the offense to make up for it.
Should Cashman seriously be worried about his job? Of course not; the Yankees will probably win a lot of regular-season games this year, and he's Littlefingered his way into a stranglehold on New York's front office anyway. But don't be surprised if fan angst gets even louder than usual if the postseason plays out the same way after a complacent winter.
Dave Dombrowski, Philadelphia Phillies
No team this side of the Yankees was more in need of a shakeup this offseason than the Phillies, fresh off of three consecutive postseason flameouts in which their offense disappeared. But pretty much all Dombrowski was able to do is keep (most of) the band together, with new contracts for Kyle Schwarber and catcher JT Realmuto by far the biggest moves of the winter.
And even that comes with a significant caveat, as both players came at an exorbitant cost — especially Realmuto, a rapidly declining catcher who somehow landed a three-year, $45 million deal that no other team would have been willing to give him. Add in the departure of Ranger Suarez in free agency, and you're left with a team that feels about the same as the one that lost in last year's NLDS ... only a year older and slightly worse.
The bullpen could be a real strength, but if Zack Wheeler can't come back healthy and Andrew Painter isn't ready for his MLB close-up, the wheels could come off here. You only get so many bites at the apple before big change is inevitable. Dombrowski couldn't find that change himself, letting Bo Bichette slip away to the rival Mets. If his Phillies can't get over the hump this time, he might be out of runway.
Craig Breslow, Boston Red Sox
You can't say the Red Sox haven't been busy. Suarez and Sonny Gray have been added to the rotation, and Willson Contreras is here to man first base (or DH, if/when Triston Casas returns) and provide some much-needed pop. Taken in totality, though, are we sure that Boston actually got much better — especially for the resources expended?
The conventional wisdom entering the winter was that the Red Sox needed another big-time bat, even assuming Alex Bregman was coming back. Then Bregman shocked everyone by bolting for Chicago, and while Contreras will certainly help, this lineup still feels light. Instead, Breslow has focused most of his efforts on remaking his starting rotation, despite already having a group of young, homegrown arms that was the envy of most organizations in the league.
Were Gray and Suarez really what this team needed? Both have already started exhibiting signs of age-related decline; Gray, in particular, is at risk of falling off the cliff if his fastball erodes to a point where hitters can simply sit on his breaking stuff. The Red Sox will no doubt be good this season; they were good last season, and they added more good players than they subtracted. I'm just not sure who this team is scaring after a winter full of curious priorities. And if they're once again a cut below the AL's elite, how much patience will Breslow be afforded?
Dana Brown, Houston Astros
After winning 106 games en route to a World Series title in 2022, the Astros have slid to 90, 88 and 87 wins over Brown's three years as head of baseball operations. Certainly that slow decline can't be entirely laid at Brown's feat; the core that Jeff Luhnow assembled got old, and owner Jim Crane stopped being quite so financially willing. Still, it's hard not to notice the decline, and Brown's inability to stop it.
A bounce-back season in 2026 would do wonders to keep him off the hot seat, but it's unclear whether Houston did enough this winter to make that happen. The good news: Swooping in for Japanese righty Tatsuya Imai was a nice bit of business. The bad news: We've just named pretty much every significant addition the Astros made over the offseason.
What's left is a pitching staff full of injury risks and unknowns behind Hunter Brown, and a lineup that's woefully out of balance — chock full of right-handed infielders but way, way short on MLB-quality outfielders. The floor is still relatively high here, and the ceiling could be too if Carlos Correa turns back the clock and Yordan Alvarez, Spencer Arrighetti and Cristian Javier get and stay healthy. That's a lot ifs, though, and it's hard to imagine this team reclaiming its place atop the AL.
Buster Posey, San Francisco Giants
Posey's arrival in San Francisco's front office was met with much fanfare; not only was he a franchise legend, but he seemed on paper to be everything his predecessor, Farhan Zaidi, was not. Fast forward 18 months or so, though, and ... well, this all still feels very Zaidi-ish, doesn't it?
Sure, Posey landed Willy Adames in his first free agency, finally bringing in a big-time name after so many misses in recent years. But that wasn't enough to keep the Giants from another frustratingly mediocre season in 2025, and Posey has followed it up by mostly fiddling around the margins. The team didn't seem particularly interested in making a run at ideal fits like Kyle Tucker, Cody Bellinger or Bichette, and Adrian Houser and Tyler Mahle aren't the boost that this rotation needed behind Logan Webb and Robbie Ray.
San Francisco tossed Zaidi overboard because they were tired of being anonymous — not particularly good, nor particularly bad, just kind of there. Posey deserves more than two seasons to figure it out, but so far, he seems like more of the same for a fan base that was already thin on patience.
AJ Preller, San Diego Padres
I don't want to be too harsh on Preller here. The Padres' ownership feud has left him with precious few resources to work with as he attempts to keep pace with a juggernaut within his own division, and he does deserve credit for making this previously sleepy franchise more relevant than it had been in quite some time.
Still, it's worth taking a step back and examining the resume here. The late Peter Seidler gave Preller plenty of resources with which to work, with tax payrolls that ranked second, sixth, third, 11th and sixth over the last five years. But he's yet to get a team out of the Division Series, and some of his decisions have come back to haunt San Diego — particularly deals for guys like Xander Bogaerts and Jake Cronenworth.
The result is that Preller now finds himself between a rock and a hard place. He needs to finally break through in order to keep himself off the hot seat, but he's spent his way to a top-heavy roster that he doesn't have the means of upgrading in the ways he needs to. The bullpen will once again be lights out, but neither the rotation nor the lineup have the sort of depth they'll need to go toe-to-toe with the likes of the Dodgers, Cubs and even the Mets. It's hard to see how this gets better before it gets worse, and Preller might not get to stick around for the rebuild.