Four Winners and Four Losers From MLB’s Winter Meetings

The back-to-back champs pulled off a big move to address their biggest weakness, while the Mets’ months-long meltdown continued.

Pete Alonso showed that lumbering sluggers still have value on the open market. / John Jones-Imagn Images

MLB’s 2025 edition of the winter meetings has come and gone, and while plenty of the biggest names from this year’s class of free agents—Kyle Tucker, Alex Bregman, Bo Bichette and Munetaka Murakami among many, many others—remain unsigned, the week in Orlando provided plenty of activity.

Four of the seven biggest contracts so far this winter were agreed to this week, and the paydays have been spread out nicely, as those seven deals have all been done by seven different teams. The winter meetings are more like an opening act to the offseason rather than a climactic meeting of the minds, though enough dominoes fell to shake things up league-wide and set in motion the activity in the months to come.

While clubs are undoubtedly re-evaluating their best paths forward from here, let’s highlight the winners and losers from baseball’s most impactful meet-and-greet.

Winners

Three-Peats

Dave Roberts’s bullpen management throughout October was nothing short of masterful—namely, the fact that he navigated the high seas of the postseason late innings without a trusted closer to speak of. Which was far from the plan, given that the team signed Tanner Scott to a four-year, $72 million deal in January. Scott’s first year in Los Angeles was a disaster, and rather than hope for a bounce-back, Andrew Friedman is doubling down on his bullpen investment with a three-year, $69 million deal for three-time All-Star Edwin Diaz to presumably handle ninth-inning duties as the franchise looks to make it three World Series titles in a row.

Spending roughly $40 million per year on two relief pitchers for the next three seasons is not a tactic any baseball executive would call shrewd, but it’s one few teams could afford, and the Dodgers are certainly one of those teams. While Diaz has had some inconsistencies year-to-year, he’s undoubtedly still one of the elite closers in the game, and should make Roberts’s life a lot easier next October.

2025’s Face-Plant Teams (at Least Some of Them)

Two of last season’s biggest train wrecks—and there was no shortage of them, to be sure—were the Orioles and Braves, and both clubs made significant moves to put the year’s struggles behind them. Baltimore made the biggest individual splash, signing former Met Pete Alonso to a five-year contract to anchor its lineup. Atlanta, meanwhile, landed two-time All-Star closer Robert Suarez to fortify its bullpen just a month after it re-signed incumbent closer Raisel Iglesias. The Braves also added veteran corner outfielder Mike Yastrzemski on a two-year, $23 million deal.

For the O’s, the move is a boon in the short-term, and part of an offseason that’s definitely been geared toward a more accelerated timeline. The team shipped 26-year-old, oft-injured starter Grayson Rodriguez for pending free agent Taylor Ward in November, and weeks later signed relief pitcher Ryan Helsley to a two-year deal where the second year is a player option.

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Baltimore endured a lengthy rebuild that saw a lot of losing in the end of the 2010s into the early part of this decade, which netted the organization an enviable cache of young, controllable talent that seemed to set the club up for big success. So far, the O’s only have two one-and-done playoff appearances to show for it. They’re clearly not done yet, and seem dead set on ensuring brighter days are in store quickly.

As for the Braves, they saw their seven-year run of postseason appearances end last year, and clearly aren’t ready to call it quits on their current contention window.

Bash Bros. 2.0

The allure of the five-tool player is a myth. Ever heard of the jack of all trades, master of none? This was the week for the masters of launching dingers.

It’s felt for some time now that the baseball world’s penchant for one-dimentional, lumbering sluggers was waning, if not in the actual marketplace than at least in the public consciousness. Josh Naylor stealing 30 bases is cool, but also a disservice to his kind. Give me a guy who’s there to do one thing and one thing only: crush baseballs into the stratosphere.

The fact that Alonso and Kyle Schwarber are each going to get paid $30 million annually for the next half decade solely to torment opposing pitchers and nothing else (Schwarber is a full-time DH, and Alonso will get there soon enough) warms the hearts of anybody who loves the long ball, which should mean everybody. Guys with physiques closely resembling slow-pitch beer league All-Stars deserve a place in this game, so kudos to these two for securing such massive paydays.

Papal Ping Pong Balls

Pope Leo’s papacy hasn’t changed the on-field fortunes of his favorite baseball team yet, but this week brought good fortune to the White Sox, who won the draft lottery and will own the No. 1 pick in the 2026 draft. It will be the first time the organization picks first in 49 years, when the club selected future Hall of Famer Harold Baines.

Time will tell if next year’s selection pans out so successfully. But if there are any breaks to be handed out to the South Siders by the man upstairs, they’ve at least got someone on the inside to put in a good word.

Losers

Mets owner Steve Cohen, left, and general manager David Stearns have let several longtime players leave this offseason. / Brad Penner-Imagn Images

Steve Cohen and David Stearns

There’s an argument to be made that, after a season that saw the team go 38–55 over its final 93 games to miss the postseason, shaking up the roster is for the best. There are several months to go before Opening Day and many accomplished players available to be acquired, so it’s far too premature to call this offseason for the Mets—or any club, for that matter—a bust just yet.

But try telling that to a Mets fan and see how they react.

The vibes for the club after the aforementioned collapse are beneath the sewer at the moment. Gone are Diaz, Alonso and Brandon Nimmo, longtime fan favorites who were crucial in the team’s run to the 2024 NLCS. Adding Devin Williams and Marcus Semien won’t be enough to convince the faithful that things are trending in a positive direction. More moves are undoubtedly on the horizon, but until those come to fruition, it’s impossible to describe the Mets’ situation as anything other than bleak.

Pirates Pipe Dreams

The Pirates’ tendency to be linked to big-name free agents this winter only to come up just short has long ago reached meme territory. The team hasn’t had a winning record in seven years, hasn’t made the playoffs in 10 and has consistently operated near the bottom of the heap in terms of annual payroll. Employing the game’s best pitching phenom in years can have the effect of cranking up the team’s sense of urgency, and there have been no shortage of insider reports that Pittsburgh has made serious pursuits for players in a higher tax bracket than the club has typically courted in recent years. 

But, in the end, coming in second place for a free agent is no different than not even entering the race. Eventually, the Pirates will need to actually convince a notable player to take their money—which, apparently, is more difficult than it sounds.

Padres

Here’s another team that was mentioned in plenty of reports over the past week, but left Orlando with little to show for it. The Padres seem to have a number of trade avenues in front of them, whether it’s moving a pitcher like Nick Pivetta or a versatile infielder like Jake Cronenworth. A.J. Preller has made a name for himself as someone unafraid to take big swings, so it would be foolish to think San Diego would be quiet for the rest of the winter. But so far, the big move hasn’t come. It’s unlikely there are many Padres fans too surprised that Suarez and Dylan Cease landed elsewhere. But given that two key contributors to last season’s success are officially gone and their replacements are unknown, San Diego lands in this section for now.

Red Sox

Prior to the winter meetings, Boston swung trades to bolster its rotation, adding Sonny Gray from the Cardinals and Johan Oviedo from the Pirates. The team missed out on signing Alonso or Schwarber, though, and will have to look elsewhere to bring in some offensive firepower.

An Alex Bregman reunion feels even more likely now, while players like Bo Bichette, Eugenio Suárez or Kazuma Okamoto could fit too. The Red Sox clearly want to add to their lineup, and while there are still plenty of options out there, leaving Orlando empty handed on that front is likely to sting for the time being.

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