Winter Meetings Day 1: Major League Baseball General Mangers Get Together
Winter meetings in Major League Baseball are a time when a lot of trades and free agent signings happen. The winter meetings this year are in Orlando. In this story, you will find a summary of the biggest stories of the first day.
There have already been some big deals, and there are rumored to be more. As expected, the Los Angeles Dodgers have been active at the winter meetings. Somewhat surprisingly, the Pittsburgh Pirates have been active, and the New York Yankees will likely do nothing. Who do you think “won” day one of the winter meetings?
Winter Meetings Day One Stories
Already on day one of the winter meetings, there have been some big stories that you do not want to miss.
Los Angeles Dodgers Make A Splash
The Los Angeles Dodgers made a major move of their own in signing top free agent Closer Edwin Diaz. The deal is for three years and $69 million, which sets an AAV record for relievers. The rich get richer. The Dodgers had a clear need in the bullpen, expect more moves.
Phillies Re-Sign Slugger
Slugger Kyle Schwarber and the Philadelphia Phillies agreed on a five-year, $150 million contract. Schwarber’s return to Philly takes one of the most coveted free agents of this winter off the board and could be the move that sparks a run of action as the winter meetings roll on. The slugger was a big contributor for the Phillies last season, and likely will be again.
Pittsburgh Pirates Are Surprisingly Active
The Pittsburgh Pirates are making an effort to put a team behind National League CY Young Award winner Paul Skenes. They made a contract offer to Schwaber. The Pirates are also one of three teams interested in utility man Willi Castro. This may not seem like big news; however, the fact that the Pirates may do anything is news in and of itself.
The other teams, by the way, are the Atlanta Braves and the Colorado Rockies. Castro, 28, was an All-Star in 2024 after a strong first half with the Minnesota Twins, but he regressed through the second half and into the 2025 season.
What Of Tarik Skubal?
Nothing has happened so far with the reigning American League Cy Young Award winner. Will the Detroit Tigers trade him? At its heart, Detroit’s choice about whether to swap Skubal now, before he reaches free agency next fall, comes down to this question: Will owner Chris Ilitch and the team’s front office place more on the opportunity to win in 2026, or will they place a greater value on the extraordinary collection of young players they would presumably acquire in a Skubal deal?
It is funny that wealthy owners, like Ilitch, seem averse to paying top-dollar for talent.
What Of the Yankees?
The Yankees are rumored to be interested in signing Michael King, and General Manager Brian Cashman said they would like to bring the versatile Cody Bellinger back. Cashman also said the Yankees are not likely to do much. This is puzzling, since the other teams in the American League East are making strides to get better.
Bo Bichette Sweepstakes
Nothing has happened so far with Bo Bichette, but the Red Sox met with him. It will be interesting to see where the good bat and poor-fielding Bichette will end up. He hits so well that he will likely have multiple suitors. He is unlikely to be back with the Toronto Blue Jays.
Conclusion
There is a very high likelihood that more news will come out of the winter meetings. It is fair to wonder whether the Yankees will do anything. The team does have a good chance to win with its current roster, but there is a lot of pressure to keep up with the Joneses.
