There isn't a better time to make a splash than at the Winter Meetings, and the fact that Kyle Schwarber, Edwin Diaz and Pete Alonso, three of this offseason's biggest free agents, all signed during the three-day event in Orlando only made that clearer.
Yet, for reasons both in and out of their control, these teams and individuals failed to do anything of note in the Winter Meetings and can be seen as clear losers.
Winter Meetings losers
Boston Red Sox
After addressing their starting rotation by trading for Sonny Gray and Johan Oviedo before the Winter Meetings, the Boston Red Sox arrived in Orlando with one main goal: add more power to a lineup in dire need of it. The end result was the Red Sox striking out on the two best power hitters out there in Schwarber and Alonso.
What's the path forward now? Sure, free agency does have some power-hitting options left, headlined by Eugenio Suarez and Munetaka Murakami, and they could look to trade for a guy like Ketel Marte, but Schwarber and Alonso are two of the premier sluggers in the sport. Marte is the only realistic addition who can make fans forget about those two, and he's going to be incredibly difficult and costly to trade for.
Simply re-signing Alex Bregman and running it back isn't good enough, yet that's becoming increasingly likely. The Red Sox had perfect fits in free agency staring them in the face — Alonso even met with them in Orlando — and still couldn't get a deal done. Not great!
Craig Breslow
The reason that the Red Sox missed on their sluggers ultimately came down to Craig Breslow's reluctance to get out of his comfort zone. As Dodgers president of baseball operations Andrew Friedman said nearly a decade ago, "If you're always rational about every free agent, you will finish third on every free agent."
Will Schwarber and Alonso be all that productive in five years? Probably not. With that, it's rational that Breslow didn't go to the lengths necessary to sign either of those players. Still, it's nearly impossible to sign a star free agent without being irrational. Deals like the one Bregman signed in mid-February last offseason rarely actually come to fruition with stars.
It'd be nice to have your best players locked in on favorable terms, but that isn't always realistic. Breslow had two perfect fits available for nothing but money (and in Schwarber's case some draft pick compensation), but he balked. With one of Schwarber or Alonso, the Red Sox could've been a dark horse pick to make a serious run in the American League. Without that big power bat, why should anyone believe this team is going to do anything but lose in the Wild Card Series again?
New York Mets
The only reason David Stearns isn't on this list is that there was never a reason to believe he was actually desperate to re-sign players he wound up losing, both Alonso and Edwin Diaz. He never went beyond three years for the latter, a reliever reportedly seeking five years at one point, and reportedly never even made a formal offer to Alonso, knowing the deal the Polar Bear wound up getting was well out of his comfort zone.
Still, there can't be a list of Winter Meetings losers that doesn't include the New York Mets. They lost Alonso and Diaz and did not make a single big-league signing. There are reasons to believe that the Mets made the right move passing on the deals Alonso and Diaz got, and there's a lot of offseason left for Stearns to turn things around, but it's inarguable that the Mets are worse now than they were in 2025.
Not a single fan base is more distraught than Mets fans, who have now watched three fan favorites depart in a matter of just a couple of weeks.
Cincinnati Reds fans
Cincinnati Reds fans had hope that the team would find a way to convince Kyle Schwarber, an Ohio native who grew up a Reds fan, to come to Cincinnati. Unfortunately, the Reds fell short in their quest, and to make matters worse, The Athletic's Ken Rosenthal ($) said that the team won't be pursuing any other star free agents — adding that the team only pursued Schwarber in an effort to bolster ticket sales.
"Unlike the Orioles, the Reds are not expected to pursue other expensive free agents. Their offer to Schwarber, a native of Middletown, Ohio, about 35 miles north of Cincinnati, was tied to their belief that his addition would help drive ticket sales," Rosenthal wrote.
Talk about a slap in the face. The Reds made it clear that they have money to spend if they choose to spend it, and with Schwarber off the board, they're simply going to pocket what they otherwise would've used to supplement their roster. The cherry on top here is that the driving force behind their Schwarber pursuit was ticket sales, not winning.
What the Reds need to learn is that winning is what ultimately drives ticket sales. Sure, Reds fans might buy more tickets at the beginning of Schwarber's tenure, but if they didnt win games with him, fans wouldn't continue to flock to the park. Cincy made the playoffs last season without Schwarber, and would be a potent team in the National League if they were to add a big bat. Greedy ownership will prevent that from happening, though, and that really stinks for the fans.
Pittsburgh Pirates
The Pittsburgh Pirates talked a big game about spending money entering the Winter Meetings, and to their credit, they made a respectable offer to Schwarber before he re-signed with the Phillies. Still, when the dust settled in Orlando, the Pirates didn't make a single notable addition, as three prime options went off the board.
Signing Schwarber would've made a massive statement that the Pirates are for real. Heck, Alonso isn't as good a hitter as Schwarber, but he, too, would've been a big-money addition that would've really elevated this team. Instead, the Pirates struck out.
Of course, there's still ample time for Pittsburgh to make moves, but as players continue to sign, fans will become increasingly skeptical that the Pirates will actually be willing to spend money. Fans have a right to feel this way, given the decades of frugalness in Pittsburgh. It's on the organization to prove everyone wrong.
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