Biggest Winners and Losers of 2025 MLB Winter Meetings
The annual MLB winter meetings have been relatively quiet so far, but there were a pair of high-profile signings on Tuesday afternoon as Kyle Schwarber re-signed with the Philadelphia Phillies and Edwin Díaz joined the Los Angeles Dodgers.
That was followed by slugger Pete Alonso agreeing to a five-year, $155 million deal with the Baltimore Orioles as the logical next domino fell following the Schwarber signing.
Will Alex Bregman, Cody Bellinger or Kyle Tucker be next to sign? Who will be the next starting pitcher to agree to a new deal after Dylan Cease set the market? Will we have any movement from the international players poised to make the move stateside?
For now, let's take a run through the biggest winners and losers from the moves that have been made, including some smaller-scale deals, along with the aforementioned Schwarber, Díaz and Alonso signings.
Winner: A Fresh Start for Vaughn Grissom
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It won't be the move everyone walks away from the winter meetings talking about, but don't sleep on the Los Angeles Angels acquiring Vaughn Grissom as a trade that could pay dividends.
Once a consensus top 100 prospect and a rising star for the Atlanta Braves when he hit .420/.463/.660 with three home runs and 10 RBI over his first 14 games in the big leagues, Grissom quickly crashed back to earth.
He eventually went the other way in the deal to acquire Chris Sale from the Braves, and he hit just .190/.246/.219 in 31 games in 2024 while spending much of the year in the minors.
Still only 24 years old and controllable through 2030, he hit .270/.342/.441 with 24 doubles, 13 home runs and 48 RBI in 96 games at Triple-A last season while starting double-digit games at all four infield spots.
At the very least, he could fill the role Luis Rengifo has occupied in recent seasons, but he has a real chance to win the starting second base job as the Angels roster is currently constructed.
Loser: The Pirates and Reds Hopes of Making a Splash
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Certain teams can be ruled out as viable suitors for a top-tier free agent simply because of their perennial unwillingness to spend, and the Cincinnati Reds and Pittsburgh Pirates both fit into that category.
However, both teams seemed ready to open their wallets for a chance to land slugger Kyle Schwarber.
According to Ken Rosenthal of The Athletic, the Pirates made a four-year offer to Schwarber in the $120 million range, which would have been far and away the largest free agency deal ever handed out in Pittsburgh. The current record belongs to the three-year, $39 million deal given to Francisco Liriano in 2015.
Meanwhile, the Reds made a five-year offer in the $125 million range, with Rosenthal offering up the following depressing nugget:
"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."
So much for a splashy addition in Pittsburgh or Cincinnati.
Winner: Steven Matz
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At this time last year, Steven Matz looked like a sunk cost for the St. Louis Cardinals coming off a season where he posted a 5.08 ERA and 1.44 WHIP in 44.1 innings while tallying negative-0.2 WAR in an injury-plagued season.
Over the first three seasons of a four-year, $4 million deal with the St. Louis Cardinals, he had a 4.47 ERA, 1.34 WHIP and 1.5 WAR in 197.1 innings, making it difficult to imagine another multi-year deal might be waiting on the horizon.
However, he reinvented himself as a reliever in 2025, posting a 3.05 ERA, 1.10 WHIP and 13 holds in 53 appearances with the Cardinals and Red Sox after he was traded at the deadline.
That impressive career renaissance, which included a 2.08 ERA in 21 games after he was traded to Boston, was enough for him to secure a two-year, $15 million deal from the Tampa Bay Rays on Tuesday.
Don't be surprised if he returns to a starting role, or at least some sort of hybrid situation on a Tampa Bay staff where roles are often fluid.
Loser: The Mets Bullpen
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There are plenty of other options on the relief pitching market, but the New York Mets are almost certainly going to have to settle for a downgrade in the closer's role after losing Edwin Díaz to the Los Angeles Dodgers in free agency.
Díaz, 31, opted out of the final two years and $38 million of his contract with the Mets at the start of the offseason, and managed to turn that into a three-year, $69 million contract with the Dodgers that set a new AAV record for a relief pitcher.
After posting a 1.63 ERA and 13.3 K/9 with 28 saves in 62 games, Díaz remains one of the game's elite bullpen arms, and he has proven he is all the way back from the torn patellar tendon that cost him the entire 2023 season.
With Ryan Helsley and Raisel Iglesias also already off the market, the Mets will now turn their attention to the likes of Robert Suárez, Pete Fairbanks, Kenley Jansen and others as they look to shore up the back of their bullpen alongside newcomer Devin Williams.
Winner: Kyle Schwarber
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The last time Kyle Schwarber was a free agent, he was coming off a 32-homer season and an All-Star selection while still actively playing in the outfield, and he landed a four-year, $79 million deal with the Philadelphia Phillies.
Now set to turn 33 years old before Opening Day next year and used exclusively as a designated hitter, he was able to secure a five-year, $150 million contract this time around to return to the Phillies.
A 56-homer, 132-RBI, 4.7-WAR campaign and runner-up finish in 2025 NL MVP balloting certainly helped his cause, as did his clubhouse value to the Phillies as one of the team's top veteran voices.
Still, it's hard not to view Schwarber as the big winner here considering he has a profile that teams have begun to place less and less value on in recent years.
After crushing 187 home runs during his first four seasons in Philadelphia, he has a legitimate shot at reaching 500 homers over the life of his new five-year deal, as he enters 2026 needing 160 more to join the club.
Winner: Pete Alonso and the Baltimore Orioles
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A year ago, the market for Pete Alonso never developed as hoped, and he wound up settling for a two-year, $54 million deal with an opt-out after one season for a chance at testing the market again.
After raising his OPS from .788 to .871 while racking up 41 doubles, 38 home runs, 126 RBI and 3.4 WAR to win NL Silver Slugger honors, he was coming off a much better season this time around and found the money he was looking for at the winter meetings.
With the Mets seemingly ready to turn the page, Alonso agreed to a five-year, $155 million deal with the Orioles, giving a young Baltimore team another power bat after they already added Taylor Ward in a trade with the Angels earlier this winter.
For Alonso, it's the long-term contract he didn't find a year ago, and locks him in through his age-35 season on a team that still has significant upside, despite a disappointing finish in 2025.
For the O's, it's a proven right-handed slugger to slot behind Gunnar Henderson in the middle of the lineup, and a massive upgrade at first base after they ranked 24th in the majors with a .679 OPS from the position in 2025.
Looking ahead to the rest of the offseason, it could also make former top prospect Coby Mayo a trade chip as they pursue upgrades for their starting rotation.
In the end, Alonso ended up costing just $5 million more than Kyle Schwarber over a matching five-year deal, and the Orioles now boast one of the best offenses in the American League.
