The Winter Meetings got off to a sluggish start, but they wound up being rather entertaining by the end. While there wasn't much activity on the trade market, we saw three of this offseason's biggest free agents, Kyle Schwarber, Edwin Diaz and Pete Alonso, come off the board in a two-day period.
Given the amount of activity, we can name several winners to emerge from this past week.
Winter Meetings winners
Pete Alonso
Ever since Alonso turned down a seven-year, $158 million deal from the New York Mets in 2023, he's been ridiculed for overinflating his value in the marketplace; while his power is prodigious, 30-something righty first basemen don't exactly have the best track record in free agency. Well, after inking a five-year, $155 million deal with the Baltimore Orioles, Alonso is now set to make over $200 million during that seven-year span.
Not only was turning down the extension the right call, but Alonso actually got a bigger deal than Kyle Schwarber, a player Baltimore wanted to sign. Clearly, they wanted Alonso more. Who would've expected that? Sure, Alonso is a couple of years younger, but both of these sluggers got five-year deals. Alonso got a higher AAV and set an AAV record for first basemen on the open market in the process.
The cherry on top for Alonso is that he's going to play half his games in a ballpark perfectly suited for his power stroke. Alonso has hit five home runs in just 10 career games and 48 plate appearances at Camden Yards. He hit 38 home runs this past season, and had he played all 162 games in Baltimore, that total would've skyrocketed to 45, per Baseball Savant. Alonso got paid, got security and should put up fantastic numbers. It's hard not to love everything about this deal for him.
Baltimore Orioles fans
Admittedly, I have questions about how this Orioles offseason will age. Trading four years of Grayson Rodriguez for one year of Taylor Ward, especially given their weakness in the rotation, was risky. Signing Ryan Helsley to be their closer, after how poorly he pitched with the Mets, was risky. Giving a five-year deal to Alonso, a power-hitting first baseman who is among the worst defensive players and base runners at his position, was risky. All of these deals could go pear-shaped in just a year's time, and they haven't added a single starting pitcher yet.
Still, I can't help but feel absolutely thrilled for Orioles fans. Their team was a massive disappointment in 2025, and despite making the playoffs in both 2023 and 2024, they haven't won a playoff game since 2014. For the first time in what feels like forever, it appears that ownership and Mike Elias feel pressure to actually try and win the World Series.
Orioles team payroll in 2022 -- $43 million
— Jacob Calvin Meyer (@jcalvinmeyer) December 10, 2025
Pete Alonso salary in 2026 -- $31 million
Can we just admire this tweet for a second? The Orioles never spent like this under Peter Angelos, and now, they've signed a proven star to anchor the middle of their lineup. Again, I have no idea how good the Orioles will be in 2026 and beyond, and there's still more work to be done. But seeing them actually make big moves has to be really cool for Orioles fans. At the very least, fans can look forward to Alonso hitting 30+ home runs and driving in 100+ runs for the next few years. That, in itself, is fun, even if a World Series ring doesn't come with it.
Scott Boras' clients
Everything about Pete Alonso's deal screams victory for the player and his agent, Scott Boras. Alonso wound up making roughly $50 million more than he would've had he accepted that 2023 extension offer. He wound up earning a higher AAV than the 2025 NL MVP runner-up in Schwarber. He joined a team that should fit his swing perfectly. The cherry on top is that Alonso got this deal after signing a short-term, high-AAV prove-it deal last winter. Many, myself included, doubted that Alonso would get the long-term deal he coveted, but Boras got it done.
Free agency began with another Boras client, Dylan Cease, signing a massive seven-year, $210 million deal with the Toronto Blue Jays, and things only got better for the super agent in Orlando. Even his other clients are set up perfectly to cash in moving forward.
Alex Bregman is now the best corner infielder available. His leverage with teams looking to add a star infielder just went through the roof. Cody Bellinger might not be the best outfielder available, but his ability to play first base makes him even more valuable now for teams that need help at that position, knowing that without Alonso, the best option is probably Kazuma Okamoto or Ryan O'Hearn.
Many have knocked Boras' methods and questioned in recent years whether the league had caught up to him, but he continues to prove why he's at the top of his field. This should be yet another huge offseason for Boras, even without a Juan Soto-type free agent to represent.
Philadelphia Phillies
For the Philadelphia Phillies to be taken seriously in 2026, they simply had to re-sign Schwarber. Not only was he the NL MVP runner-up after hitting 56 home runs, but he's also seen as the leader of the clubhouse in Philadelphia and is beloved by the fans. Even if it took an extra year than the Phillies might've preferred, they got it done, and honestly, that's all that matters.
Will Schwarber be a productive player in 2030? Time will tell, but the Phillies couldn't really care less about that. Their window to win is right now, and doing so without Schwarber would've been awfully difficult.
The Phillies were facing steep competition, from big-market suitors like the Boston Red Sox and New York Mets to Schwarber's hometown team in the Cincinnati Reds. Still, they made it clear from the outset how much of a priority Schwarber was, and they put their money where their mouths were. Not many teams would've gone out of their way to sign a 32-year-old DH, so credit the Phillies for getting it done when they had to.
Los Angeles Dodgers
The Los Angeles Dodgers have won back-to-back World Series titles, and even if they'd done nothing this winter, they would've been favored to win a third. As MLB fans have become accustomed to, though, the Dodgers always leave no stone unturned when it comes to trying to improve their roster, and they did so again at the Winter Meetings while addressing their biggest Achilles heel.
The Dodgers landed arguably the best closer in the game, Edwin Diaz, and did so on a three-year deal. Yes, it set an AAV record for a reliever, but L.A. stayed away from the five-year commitment Diaz was reportedly seeking, and should get the rest of Diaz's prime years at the back end of their bullpen.
Relievers are incredibly volatile, so it wouldn't be the most shocking thing in the world to see Diaz struggle in 2026, as Tanner Scott did in 2025. But Diaz is as reliable as any closer in the game, and at the end of the day, the Dodgers got the best option available to fill the biggest hole on their roster. They would've been winners even if they'd given Diaz the big deal he wanted, so only having to commit three years to him makes them even bigger winners.
Edwin Diaz
Signing Diaz could not make more sense for the Dodgers, but can we talk about how great this is for Diaz himself? Look, I'm sure he loved being a New York Met, and Mets fans certainly loved him, but is there a better scenario for him than getting to live in Southern California while joining a team that'll be favored to win the World Series throughout his entire contract?
The Mets say they want to win every year, but ultimately, they made the playoffs just twice in Diaz's six-year tenure and made it past the Wild Card round just once. They have the resources to win, but they haven't done so yet. If Diaz wants to compete for titles, and all indications are that he does, what team is better to join than the Dodgers?
29 of MLB's 30 fan bases certainly hate this outcome, but it's inarguable that Diaz got just about everything he could've wanted. He clearly wanted to be a Dodger, based on his refusal to give the Mets a chance to match or top the Dodgers' final offer, and he got to set an AAV record for his position to boot.
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