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.
Schwarber was No. 3 on Yahoo Sports’ list of the top 50 free agents, behind Kyle Tucker and Alex Bregman, while Díaz ranked 11th.
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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.
Tuesday will also see the MLB Draft Lottery, and Wednesday will deliver the Rule 5 Draft. The Chicago White Sox have the best odds to land the first overall selection in the 2026 MLB Draft at 27.7%, but 14 other teams could walk away with the top pick.
Follow along with Yahoo Sports for all the news, rumors and hot stove drama from the 2025 winter meetings:
Live22 updates
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 everyday player.
Jack Baer
We now know the terms of a deal that broke Monday night, as it’s a two-year, $15 million year for Steven Matz from the Rays, who also added center fielder Cedric Mullins this week.
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.
Chris Cwik
It’s not a baseball winter meetings until Scott Boras starts making puns about his clients. This time around, however, Boras appears to be feeding some rumors with his comments.
When asked about free-agent outfielder Cody Bellinger on Tuesday, Boras implied the Los Angeles Dodgers could be involved for his client.
The Dodgers are in the market for another outfielder after Michael Conforto struggled in his one season with the club. Conforto would up being left off the team’s postseason roster. That didn’t stop the Dodgers from winning it all.
If Bellinger signs with Los Angeles, it would be a reunion for the slugger. Bellinger started his career with the Dodgers, spending his first six seasons with the team. After leaving, Bellinger has remained an effective player, posting a .281/.338/.477 slash line over the past three years.
Chris Cwik
The Boston Red Sox are considering a number of big moves this offseason. The team is among those reportedly interested in trading for Arizona Diamondbacks superstar Ketel Marte, according to Ken Rosenthal of The Athletic.
The D-backs are looking for a “superstar-type return” in exchange for Marte, an executive told Rosenthal, so Boston would have to be willing to part with a lot for the second baseman.
The Red Sox are also considering a reunion with Alex Bregman after the third baseman put up strong numbers in Boston last year. Bregman hit .273/.360/.462 in a bounce-back season. He opted out of his deal after just one season, hitting the market again this winter.
The team has also expressed interest in Isaac Paredes. If Boston acquires Paredes from the Houston Astros and brings back Bregman, Paredes would shift to first base in Boston, per Rosenthal.
Jason Owens
Shohei Ohtani will again represent Japan in the World Baseball Classic to be played in March.
Dodgers manager Dave Roberts would prefer that Ohtani stick to hitting. He doesn’t want his two-way, MVP star putting his arm at risk pitching in the international competition. Roberts told reporters Monday that he has not discussed this preference with Ohtani.
Jason Owens
The Los Angeles Dodgers won a second consecutive World Series in November with a star-laden, high-priced roster. Manager Dave Roberts, understandably, sounds content running it back with the same core.
Roberts told reporters Monday that he doesn’t envision any big offseason spending this winter.
“There’s really no big splash that we feel that needs to be made,” Roberts said.
Among the roster specifics, Roberts projects that Mookie Betts will continue to play shortstop in 2026. Betts played the past two seasons in the infield after playing primarily as an outfielder in his previous 10 MLB seasons.
Criss Partee
The Arizona Diamondbacks are open to engaging with teams on Ketel Marte. However, the price is high, with an emphasis on starting pitchers who are at (or near) the major-league level. Marte appeared in 126 games for Arizona last season, hitting .283 with 28 home runs, 72 RBI and a .893 OPS.
Chris Cwik
One of the biggest names on the MLB free-agent market is going to meet with clubs in person at the winter meetings. Former New York Mets slugger Pete Alonso will reportedly meet with both the Boston Red Sox and Baltimore Orioles at the event, which is being held close to his offseason home in Florida, according to Jon Heyman of the New York Post.
Alonso, 31, experienced a resurgent season with the Mets, hitting .272/.347/.524, with 38 home runs over 162 games. Alonso was in need of a strong season after limping into the free-agent market last year after underperforming. That caused him to take a short-term deal to return to the Mets. That deal contained on opt-out after one year, which he exercised after a strong 2025.
Both the Orioles and Red Sox could use another slugger to add to their lineups. Alonso is among the biggest power bats on the market. He should draw plenty of interest around the league and have plenty of opportunities to meet with other clubs at the winter meetings.
Chris Cwik
The San Diego Padres are looking to rebalance their payroll this offseason, which could lead to some surprising names being dangled on the trade block. Despite being the team’s presumptive No. 1 starter following the departure of Dylan Cease, Nick Pivetta could be one of the players the Padres consider parting with in the offseason, per Dennis Lin of The Athletic.
A deal — which would require a steep return — would allow the Padres to get some payroll relief. The team is projected to carry a $201 million payroll next season. Pivetta is set to earn $19 million next season, a bargain considering he just posted a 2.87 ERA and finished sixth in Cy Young voting but a major increase after he made just $1 million last season.
Infielder Jake Cronenworth, who is owed $60 million over the next five years, could also be on the block. Cronenworth, 31, turned in a solid but unspectacular season in 2025, hitting .246/.367/.377 with 11 home runs. While his contract is spread out over five years, it could be tough to move a utility infielder who has struggled with the bat in recent years.
Chris Cwik
The Kansas City Royals are looking to remake their outfield this winter. The team is reportedly looking for two new outfielders but isn’t shopping at the top of the free-agent market, per Ken Rosenthal of The Athletic.
Instead, the Royals are targeting one of Adolis García, Max Kepler, Mike Yastrzemski or Mike Tauchman, and the team is hoping to acquire another outfielder via trade. Pitcher Kris Bubic could be made available in a deal for an outfielder, per Rosenthal.
The Royals are looking to overhaul their outfield, with right fielder Jac Caglianone as the only consistent player sticking around next year. Caglianone disappointed as a rookie, hitting just .157, but he has power potential and strong enough minor-league numbers for the team to continue to have faith in the youngster.
Chris Cwik
There’s a surprising entrant for free-agent designated hitter Kyle Schwarber: The Pittsburgh Pirates. Pittsburgh has reportedly made an offer to Schwarber for four years. It’s believed the contract exceeds $100 million, per Ken Rosenthal of The Athletic.
Despite that, the Pirates are not a strong candidate to sign Schwarber, per Rosenthal. The 32-year-old slugger has also received interest from the Philadelphia Phillies, Boston Red Sox and Cincinnati Reds. All three of those clubs are contenders, making it more likely that Schwarber joins one of them if they present strong contract offers.
Schwarber is coming off arguably his best season in the majors. In 724 plate appearances, Schwarber hit .240/.365/.563 with a league-leading 56 home runs. While his age is a concern — Schwarber will be 33 before next season — he continues to be one of the best sources of walks and power in the game.
Mon, December 8, 2025 at 7:45 AM PST
Russell Dorsey
In a sport like baseball, every transactional move, whether it’s a free-agent signing or a trade, comes with some level of inherent risk.
The risk of a free-agent signing is overpaying on the deal, either because the player doesn’t perform to the level of the contract or because the back half of the deal goes bad as he declines.
A trade adds different layers of risk: either losing blue-chip prospects in exchange for the player being acquired or losing an impact big leaguer to obtain unproven prospects who might never pan out. In every transaction, it’s the responsibility of front offices to mitigate that risk while making calculated decisions that make the gamble worth it in the pursuit of winning.
Risk mitigation in baseball can be a double-edged sword. Yes, the need for caution comes with the job title for any general manager or president of baseball operations, as balancing the present against the future is a critical part of the gig. However, the adage “fortune favors the bold” has also shown itself to be true in baseball, specifically when it comes to player acquisition.
As Milwaukee Brewers president of baseball operations Matt Arnold put it, “If you haven’t made a bad trade, you haven’t made enough trades.”
Chris Cwik
Few MLB pitchers are more frustrating than Dylan Cease. When he’s on, Cease looks like a future Hall of Famer and perennial Cy Young contender. When he’s off, he looks like a back-end starter incapable of finding the zone.
The Toronto Blue Jays are betting that the “on” version is Cease’s true form. Cease reportedly agreed to a seven-year, $210 million deal with Toronto on Wednesday, according to Jon Heyman of the New York Post.
With the contract, Cease joins the reigning AL champions — and a franchise that apparently has no interest in sitting on its hands after a heartbreaking World Series loss. The Blue Jays were already one of the highest-spending clubs in MLB, ranking fifth among 2025 payrolls and signing franchise star Vladimir Guerrero Jr. to a $500 million extension, and now they’ve struck for the first big deal of the offseason.
The right-hander gives Toronto a formidable rotation on paper: Cease, Kevin Gausman, Trey Yesavage, Shane Bieber and José Berrios. Those are four proven veterans and one of the breakout stars of the 2025 postseason in Yesavage.
Of course, this all presumes the Blue Jays can turn Cease into his ideal self. Otherwise, this contract might not compare well to other big-time pitcher deals in recent history.
Chris Cwik
Mike Soroka is reportedly in agreement with the Arizona Diamondbacks on a one-year deal, according to ESPN’s Jesse Rogers.
Soroka, 28, split time between the Washington Nationals and Chicago Cubs last season. After showing some interesting, new skills in Washington, Soroka was traded to the Cubs at the deadline. He pitched just 8 1/3 innings with Chicago due to injury.
Soroka, who missed both the 2021 and 2022 seasons due to injuries, has been a solid, but unspectacular pitcher throughout most of his career.
He brings a career 3.85 ERA to Arizona next season.