ORLANDO, Fla. — Day 2 of the Winter Meetings had considerably more action than Day 1, though most of it was concentrated around a half-hour stretch of midday when two of the market’s top free agents agreed to new contracts just as the sport’s most powerful agent was addressing the media and dropping cryptic hints about the teams involved in negotiations.
Pretty standard stuff for the Winter Meetings.
The third and final days of this year’s meetings will be on Wednesday. For now, just to make sure you didn’t miss anything, here’s a rundown of the biggest news from Day 2.
Biggest signing so far
The top of the free agent market had been dormant for weeks until just before noon on Tuesday when Kyle Schwarber, the No. 4 free agent on the Big Board, signed a five-year, $150-million deal with the Philadelphia Phillies.
Nothing about the signing came as a surprise — Schwarber returned to the team he’d been with since 2022, and the contract was almost exactly what The Athletic predicted more than a month ago — but it was the first massive offense splash in what had been a pitching-heavy offseason. It also helped clarify things for one of the winter’s most interesting teams, the Phillies, who remain well within their competitive window but face meaningful roster turnover.
The Schwarber signing could also loosen a logjam in a free agent market that’s relatively deep at first base/designated hitter.
Dodgers add top free agent reliever (again)
At almost the exact moment when the Schwarber news broke, The Athletic’s Will Sammon broke the news that top free agent closer Edwin Díaz was signing a three-year, $69-million deal with the Los Angeles Dodgers. After the Tanner Scott signing last winter, this is the second offseason in a row that the Dodgers signed the Big Board’s top-ranked reliever.
Díaz, 31, has been with the Mets since 2019, establishing himself as one of the most reliable closers in baseball. He’s coming off a resurgent season in which he made his third All-Star Game and led all NL relievers in Win Probability Added.
In L.A., Díaz will presumably take over as closer, a role in which Scott struggled last season. At $23 million, Diaz’s new contract pays the highest average annual value ever for a relief pitcher.
Boras holds court, talks in code
Every Winter Meetings, agent Scott Boras schedules a media scrum in which he answers questions with a prepared series of puns, metaphors and comedic talking points.
Among those talking points on Tuesday was a coded message suggesting Cody Bellinger’s market includes — if we’re reading the tea leaves correctly — the Yankees, Reds, Mets, Dodgers, Phillies, Giants, Blue Jays and Angels. Here’s what Boras said:
“It’s not for me to judge, but great players see red if they have a big bat yanked out of their lineup. I haven’t met a team that dodges a five-tool player. To fill the center-field need is a giant step towards the playoffs. North and South outfielders that fly with power, they’re rare birds. In the offseason, there’s a lot of startup to organizations, and for that reason, there’s a lot of angel investors that are looking for very versatile outfielders. So, other than that, Belli doesn’t have much interest.”
Boras was also front-and-center on MLB’s main stage as part of a press conference introducing newly minted Toronto Blue Jay Dylan Cease, who agreed to a seven-year, $210-million contract with the club last week.
Diamondbacks laying groundwork for Marte trade?
Ken Rosenthal reported Tuesday that the Arizona Diamondbacks are discussing second baseman Ketel Marte in various trade talks, and even if a deal doesn’t come together by the end of the week, those talks could set the stage for a Marte deal later this offseason.
Marte, 32, is signed for another six years, $102.5 million, a relative bargain for one of the best middle infielders in baseball. Rosenthal reports that the Diamondbacks are seeking a “superstar-type return,” but a deal could come together for teams willing to pay the price (and willing to accept the risk of clubhouse concerns that showed up in Arizona).
Among the teams that could be a fit in the end are the Boston Red Sox, who — according to Rosenthal — are exploring various avenues toward improving their offense. They’re in on free agents Alex Bregman, Bo Bichette and Pete Alonso, while also considering trade candidates Marte and Houston Astros third baseman Isaac Paredes.
Mets dangling All-Star starter Peterson
In their search for offense, the New York Mets could dangle one of their most reliable starting pitchers. Tim Britton and Will Sammon reported Tuesday that the Mets are willing to trade All-Star starter David Peterson, who’s in his final year of team control and led the team with 168 2/3 innings last season.
According to the report, the Mets are primarily interested in trading Peterson in a need-for-need deal similar to their previous trade of outfielder Brandon Nimmo for second baseman Marcus Semien. The Mets have needs at first base and designated hitter, as well as in the outfield and bullpen.
Orioles show willingness to spend
With relatively new ownership, a load of young talent, and an obvious need for starting pitchers, the Baltimore Orioles are a fascinating team this offseason, and reporting today suggests they’re willing to spend at the top of the free agent market. Rosenthal reporting that the Orioles matched the Phillies’ $150-million offer to Schwarber. Further, Rosenthal reported that the Orioles have been involved in talks for basically every top free agent except infielders Alex Bregman and Bo Bichette, neither of whom has a positional fit in Baltimore.
Team USA adds Schwarber, Henderson, Smith, Turang
Tuesday was unofficially World Baseball Classic Day at the Winter Meetings, and Team USA marked the occasion by announcing that Schwarber, Gunnar Henderson, Will Smith and Brice Turang will join a roster that already included Aaron Judge, Paul Skenes, Cal Raleigh, Bobby Witt Jr., Corbin Carroll and Pete Crow-Armstrong.
Among the other WBC happenings on Tuesday was news of Cuban reliever Aroldis Chapman potentially pitching for Great Britain (he’s eligible because his parents immigrated to Cuba from Jamaica, which was a British colony until 1962). Also, Team Venezuela vocally defended its country and citizens amid rebukes and threats from President Trump.
White Sox win draft lottery
The Chicago White Sox won Tuesday’s draft lottery, giving them the No. 1 pick in next summer’s draft. They’ll be followed by the Tampa Bay Rays and Minnesota Twins. The Colorado Rockies, coming off the worst record in 2025, should have gone into the lottery with the best odds of picking No. 1, but they were ineligible after receiving lottery picks in the past two drafts, so they’ll pick 10th.
Red Sox, Angels make minor trade
In a small but notable deal, the Boston Red Sox sent infielder Vaughn Grissom to the Los Angeles Angels for 21-year-old outfield prospect Isaiah Jackson. Grissom was the primary return in the 2023 trade that sent Chris Sale to the Atlanta Braves. He has since struggled with injuries and underperformance and spent all of 2025 in Triple-A, producing a .783 OPS while playing all four infield positions. Still just 24 years old, Grissom has played parts of three seasons in the Major Leagues and shown some promise as a versatile, bat-first middle infielder.
Phillies extend manager Thomson
On Day 1 of the Winter Meetings came word that the Phillies were nearing a deal with Don Mattingly to be their new bench coach. On Day 2, the Phillies announced that they have extended manager Rob Thomson through the 2027 season. Thomson became interim manager in 2022 and promptly guided the team to the World Series. He’s been to the playoffs each of his four seasons in the job, including back-to-back division titles the past two years.
Baldelli joins Dodgers as special advisor
Former Minnesota Twins manager and Tampa Bay Rays outfielder Rocco Baldelli has joined the Los Angeles Dodgers front office as a special assistant. Baldelli has an extensive history with Dodgers president of baseball operations Andrew Friedman, who previously served as the Rays general manager.