The big-name signings continued Wednesday at MLB’s winter meetings as Pete Alonso joined the parade, signing a five-year, $155 million deal with the Baltimore Orioles, ESPN’s Jeff Passan reported.
It had been a fairly slow MLB offseason leading up to this week’s winter meetings, but the first major domino fell Tuesday morning, with Kyle Schwarber reportedly finalizing a five-year, $150 million deal to return to the Philadelphia Phillies. Just minutes later, news broke that Edwin Díaz and the reigning champion Los Angeles Dodgers are reportedly in agreement on a deal.
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Schwarber was No. 3 on Yahoo Sports’ list of the top 50 free agents, behind Kyle Tucker and Alex Bregman, while Díaz ranked 11th. Alonso ranked fifth in the rankings.
MLB executives, agents and many others are congregating in Orlando, Florida, this week to hash out deals in the biggest event of baseball’s offseason. Last year’s winter meetings saw Juan Soto’s record $765 million deal with the New York Mets, the Garrett Crochet blockbuster trade to the Boston Red Sox, Max Fried landing with the Yankees and several other major moves.
This year, Chicago Cubs outfielder Kyle Tucker is looking for a contract that could surpass $300 million, while Detroit Tigers ace Tarik Skubal might be on the trade block. The Washington Nationals seem likely to deal MacKenzie Gore, and several other free agents could land nine-figure deals.
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Tuesday also saw the White Sox land the No. 1 pick in the MLB Draft lottery, and Wednesday will deliver the Rule 5 Draft.
Follow along with Yahoo Sports for all the news, rumors and hot stove drama from the 2025 winter meetings:
Live34 updates
Chris Cwik
Pete Alonso bet on himself in 2025, and it paid off in a major way. Alonso reportedly agreed to a five-year, $155 million deal with the Baltimore Orioles on Wednesday, ESPN’s Jeff Passan reported.
The contract comes a year after Alonso, 30, struggled to secure a long-term deal on the free-agent market.
With the move, the Orioles finally have their big-name free agent. Baltimore reportedly made a competitive offer for Kyle Schwarber before he signed a five-year, $150 million deal with the Philadelphia Phillies and had contacted outfielder Kyle Tucker about a deal. With the Alonso deal, Baltimore finally got their star slugger.
Alonso fits in well with the Orioles, who were looking for an upgrade over Ryan Mountcastle at first base. While Mountcastle has shown flashes as a hitter in the past, he was well below league-average in that area last season. Alonso immediately gives the team a middle-of-the-order power bat capable of posting big power numbers regardless of his ballpark. That should work out well in Baltimore, where righties have had a tough time hitting home runs since the team altered the wall in left field.
Chris Cwik
Former New York Mets slugger Pete Alonso appears to be a popular target at the winter meetings. But of all the teams interested in Alonso, the Mets, Baltimore Orioles and Boston Red Sox have emerged as favorites to sign the first baseman, per MLB.com’s Mark Feinsand.
Alonso, 31, is coming off a season in which he hit .272/.347/.524. It was a comeback year for Alonso, who struggled in 2024, tying his career-low with a 122 wRC+.
That led to Alonso taking a lesser deal on the free-agent market last season. That deal included an opt-out after just one season, allowing Alonso to rebuild his value before hitting the free-agent market again this winter.
This time around, Alonso seems like a safe bet to secure the contract he sought last winter. It helps that at least three teams seem to be fighting for his services.
Jack Baer
It’s reportedly a two-year, $19 million contract with $1 million in incentives for Finnegan, per Fansided’s Robert Murray. A nice windfall for a reliever who was good for the Tigers in the regular season, but faltered a bit in the ALCS.
Jack Baer
The Tigers acquired Kyle Finnegan at the trade deadline this year and appear to want some more innings from him. The team is closing in on a deal with the reliever, according to The Athletic’s Ken Rosenthal.
Jack Baer
With a new president of baseball operations embarking on a new era, the Nationals appear likely to trade starting pitcher Mackenzie Gore this winter. According to MLB Network’s Jon Morosi, their geographic rival is a potential trade partner.
Trading Gore to the Baltimore Orioles would be notable for reasons beyond what’s on the field, as the two franchises have been in something of a standoff since the Nats came to town, with tensions exacerbated by a perpetual feud over a TV deal resolved earlier this year.
Jack Baer
The Dodgers struck big today with the Edwin Diaz deal, but still have a notable need in the outfield. They landed the biggest reliever on the market, so why not Kyle Tucker, the biggest outfielder on the market?
Per The Athletic, the defending champions are interested in Tucker, but not on a six- or seven-year deal. They’d instead be willing to go for a three- or four-year deal with a super-high average annual value. This isn’t the first time they’ve tried to make that pitch, though, and most players turn them down. Still, it’s something to watch if Tucker’s market doesn’t develop as hoped.
Jack Baer
A lot of teams appear to want one of the best second basemen in baseball.
Jack Baer
The Marlins are engaged in trade talks with the Baltimore Orioles and other clubs about starting pitcher Edward Cabrera, according to The Athletic. Cabrera was solid in 2025 with a 3.53 ERA in 137 2/3 innings but also hit the injured list twice, once with an elbow sprain.
It’s unclear what the Marlins are asking for and how ready they are to pull the trigger, but teams value controllable starting pitchers highly enough that it makes sense they’re looking into it. Cabrera is under team control through 2028.
Jack Baer
Jack Baer
The Pirates didn’t get Kyle Schwarber today, but they did get New York Mets reliever Gregory Soto! The two-time All-Star gets $7.75 million from the Bucs after posting a 4.18 ERA and 3.91 xERA in 60 1/3 innings last season.
He is not the best reliever to leave the Mets today.
Jack Baer
The Ketel Marte market still seems to be forming, but MLB Network’s Jon Morosi says the Red Sox are seen as a strong contender.
Jack Baer
The White Sox entered the 2026 MLB Draft Lottery with the best odds for the top pick, at 27.73%. It worked out for them, as they received their first No. 1 pick since 1977 (Harold Baines) on Tuesday.
Here’s the top 10:
1. Chicago White Sox
2. Tampa Bay Rays
3. Minnesota Twins
4. San Francisco Giants
5. Pittsburgh Pirates
6. Kansas City Royals
7. Baltimore Orioles
8. Athletics
9. Atlanta Braves
10. Colorado Rockies
Jack Baer
The two-time Gold Glover posted an .808 OPS against righties and .676 OPS against lefties in 2025. It looks like the Red Sox are still going to give him a shot as an every-day player.
Jack Baer
We now know the terms of a deal that broke Monday night. It’s a two-year, $15 million year for Steven Matz with the Rays, who also added center fielder Cedric Mullins.
Jack Baer
There wasn’t much suspense after Edwin Diaz’s deal with the Dodgers, but it’s official: Devin Williams will be closing games for the Mets in 2026.
Chris Cwik
The Baltimore Orioles are looking to make a splash this winter. The team has reportedly had conversations with Kyle Tucker, the premier hitter on the market, according to Jon Morosi of MLB Network.
Tucker, 28, is coming off a season in which he hit .266/.377/.464 as a member of the Chicago Cubs.
The news comes after reports suggesting the Orioles offered Kyle Schwarber a five-year, $150 million contract. Schwarber opted to take that same deal with the Philadelphia Phillies, however.
Both items make it clear the Orioles are looking to add big-name talent this winter. After missing out on Schwarber, it’s possible the Orioles step up their pursuit of Tucker.
Chris Cwik
Expectations were high for Vaughn Grissom when the Boston Red Sox made him the centerpiece of the Chris Sale trade. But injuries wrecked Grissom’s time in Boston, leading to the team trading the shortstop to the Los Angeles Angels on Tuesday, according to ESPN’s Jeff Passan.
Grissom, 24, will now look to reestablish himself in the majors with his third professional team. The Red Sox will receive outfielder Isaiah Jackson in exchange for Grissom.
As a member of the Atlanta Braves, Grissom flashed as a potential star in his first taste of the big leagues. Injuries pushed him to the majors as a 21-year-old, where he more than held his own with the bat. As a rookie, he slashed .291/.353/.440 over 156 plate appearances.
Grissom was expected to open the 2023 MLB season as the Braves’ shortstop after Dansby Swanson left in free agency. But he failed to win the job in spring training and then spent the majority of the season in the minors. He received just 80 plate appearances in the majors that year, hitting .280/.313/.347.
While it was a disappointing performance, the Red Sox still saw something in Grissom’s bat. That December, Boston traded Sale to the Braves in exchange for Grissom and cash. The move was essentially a salary dump by Boston, which no longer wanted to pay Sale’s lengthy contract. Although Grissom was coming off a rough season, he was still young, and the memory of his rookie season hadn’t faded just yet.
Tue, December 9, 2025 at 11:28 AM PST
Jack Baer
One of the top relievers in baseball is reportedly heading to Los Angeles.
Former New York Mets closer Edwin Díaz has agreed to a contract with the Los Angeles Dodgers, according to The Athletic’s Will Sammon. Per ESPN’s Jeff Passan, the deal is for three years and $69 million.
Because Díaz rejected a one-year, $22.025 million qualifying offer, the Mets will receive draft pick compensation for his exit.
Díaz was easily the top arm on the bullpen market this offseason, ranking at No. 11 on Yahoo Sports’ list of top 50 free agents, 16 places ahead of the next reliever.
Read more on Diaz here.
Chris Cwik
Kyle Schwarber will be staying in Philadelphia after all.
According to ESPN’s Jeff Passan, Schwarber and the Phillies are reportedly finalizing a five-year, $150 million contract.
Schwarber, 32, was expected to be one of the most coveted players on the market after smashing a career-high 56 home runs last season and finishing second in the NL MVP vote.
Schwarber is the king of what is known as the “three true outcomes” in baseball: home runs, walks and strikeouts. That phrase is typically used to describe players whose plate appearances most often end in one of those three results.
Schwarber fits that bill perfectly. Since his major-league debut back in 2015, Schwarber has a 14.2% walk rate and 28.4% strikeout rate and has hit 340 home runs. Those figures rank ninth, 10th and second, respectively, among players with at least 3,000 plate appearances over that period.