Winter Meetings 2025 Winners and Losers for the Meetings that Can Shape How Baseball Teams Fare
The winter meetings in baseball finished on Wednesday, and now we can look back and posit some winners and losers. The signature event of the winter meetings was that not much happened. The biggest moves of the winter meetings were the signings of Edwin Diaz (Dodgers), Kyle Schwaber (Phillies), and Pete Alonso (Orioles).
Aside from these free agent signings, these winter meetings will be remembered for the lack of movement. Perhaps teams were paralyzed by the looming 2027 work stoppage. Whatever the reason, there were marquee players who should have been available. Were you disappointed by your favorite team’s relative inaction?
Winner in the Winter Meetings: Pete Alonso
The Polar Bear made a big slash at the winter meetings. Some would say this was the only major move of the winter meetings. Ironically, the contact was agreed to on the last day of the winter meetings. Alonso signed with the Baltimore Orioles, who reached terms on a five-year pact with free-agent first baseman Pete Alonso. Alonso is leaving the Mets and will earn $31 million annually, or $155 million over the life of the contract.
Winner in the Winter Meetings: Kyle Schwarber
The terms of the deal Kyle Schwarber signed were for five years and $150 million. With that contract, the Philadelphia brought their big Slugger back. The Phillies have an aging roster and signaled with this deal that they are going for it, with the players who got them to the lofty position they occupy. Then again, this group of players has not won a World Series. Nevertheless, the Phillies’ lack of success has not deterred them from making a big splash with this contract.
Winter Meetings Loser: Mets General Manager David Stearns
David Stearns has been the Mets’ top baseball operations executive for more than two years now, and he’s starting to feel the heat after missing the postseason and allowing both Pete Alonso and Edwin DÃaz to leave through free agency. Factor in the Brandon Nimmo trade earlier this winter for second baseman Marcus Semien, and the Mets will have a new core heading forward.
The key for Stearns is getting what comes next correct. During his time running the Milwaukee Brewers, he uncovered highly productive bullpen arms and first basemen. Whoever Stearns lands on here might not make for the same quality of headline. He already signed former Yankees reliever and rebound candidate Devin Williams to a multi-year deal, but they could help reshape the Mets without requiring the same kind of costly long-term investments.
Winter Meetings Winner: Chicago White Sox
The White Sox won Tuesday night’s Draft Lottery, ensuring they will make the Number one selection for the first time in nearly fifty years. Previously, the White Sox selected, but did not sign, catcher Danny Goodwin in 1971 and outfielder/DH Harold Baines in 1977. Baines went on to author a Hall of Fame career that included parts of fourteen seasons with the White Sox.
Look for the White Sox to select UCLA shortstop Roch Cholowsky. Cholowsky is an athletic shortstop who hit .353/.480/.710 last season with 23 home runs, seven of eight stolen bases, and 15 more walks than strikeouts. The only other UCLA player to be selected number one overall was Garrit Cole.
Loser of the Winter Meetings: Market Clarity
Four of CBS Sports’ top five (and seven of the top 10) ranked free agents remain available. This includes players like outfielder Kyle Tucker and infielder Bo Bichette. Most of the top trade targets remain in place, too, like Tarik Skubal and Paul Skenes, the reigning Cy Young award winners.
Nobody knows what is going on, but the looming work stoppage is one factor. Another could be the historic lull around the holidays. One thing is for sure: most of the big names have not been traded or signed as free agents.
Conclusion
There was a reason why market clarity brought up the rear in this article. The winter meetings ended on Wednesday with not much happening. There are a lot of high-profile baseball players still available to be traded or signed.
