Yankees 2025 Winter Meetings Rumors: Day Two

Well, day one at the 2025 Winter Meetings were mostly a bust. There were rumors, but not exactly many of the more juicy variety, and the day was almost completely devoid of actual activity. We did at least hear from Yankees brass, with Brian Cashman telling us that while he doesn’t feel they have as much work to do this offseason compared to last. Aaron Boone also spoke, and posited that the difference between his team and the AL champion Blue Jays is smaller than the public’s perception.
We now head to round two, hopeful that something will happen. It doesn’t have to be a Kyle Tucker mega-deal, but seeing any team, not necessarily the Yankees, deign to at least sign a reliever to a two-year deal would be a boon. In any event, stick with us as the rumor mill spins up. If/when the action starts to heat up, we’ll have you updated with all that’s coming out of Orlando.
Rumors of the Day (December 9)
2:40 PM: We have another move, after a few hours of vague rumors — some of which include Detroit and Boston being interested in Ha-Seong Kim and Eugenio Suárez, respectively. There’s also been the standard Scott Boras chatter, which we don’t really care about since he’s just doing his job and generating chatter for his clients.
Here’s a real Red Sox note: they’ve traded Vaughn Grissom to the House of Bizarre that is the Los Angeles Angels for 2025 eighth-rounder Isaiah Jackson, an A-ball outfielder. If you’ve forgotten Grissom, he debuted with Atlanta a couple years ago and then was the main piece that Boston got back in its regrettable (for them, anyway) trade of Chris Sale, who promptly won his first career Cy Young Award. Grissom was awful for the 2024 Red Sox and spent all of 2025 at Triple-A. So, sure, sounds like an Angel.
11:15 AM: The first major domino of the Winter Meetings has fallen at last. You can not-so-shockingly kiss those Kyle Schwarber/Pirates goodbye, as according to Jeff Passan, the Phillies are bringing the NL MVP runner-up back on a five-year, $150 million deal — nearly double what Schwarber first signed to come to Philly in the winter of 2021-22. It’s a hefty price tag for a DH, but the Phils love everything that Schwarber brings to both the lineup and the clubhouse writ large, plus their owner is definitely championship-driven rather than purely profits-driven. (Oh, and Rob Thomson is getting extended through 2027. Good for Topper.)
But that’s not all! Remember that Edwin Díaz/Dodgers rumor from just a few minutes ago? To reference an overused meme, that escalated quickly. Mets beat writer Will Sammon has reported that the 2025 NL Reliever of the Year is signing with LA. They’re going big on relief pitching again this offseason even after getting burned by Tanner Scott and Kirby Yates. Edwin is a safer bet than them and Shohei Ohtani (not to mention multiple championships) helps bring in so much extra money that no one cares anyway. Goodness. The contract terms: three years and $69 million. Sounds like he really wanted to be a Dodger!
10:50 AM: Some relief market buzz: Jon Heyman has the Dodgers and a good ol’ fashioned Mystery Team joining the Mets and Blue Jays in the Edwin Díaz sweepstakes. Will “Narcos” be playing somewhere other than Queens in 2026?
10:30 AM: Ken Rosenthal added to the Ketel Marte/Red Sox buzz in his columns this morning, though in general, Rosenthal all but agreed with Jon Heyman’s report from yesterday that the Diamondbacks are looking for big return for their longtime second baseman. That “might take some time for teams to warm to,” per Rosenthal,“ like Daulton Varsho a few years ago.
Also in one of the columns: the Astros and Red Sox appear to be talking about a possible deal for Isaac Paredes, who has ping-ponged from the Rays to the Cubs to the Astros over the past couple years and now might move again. Rosenthal didn’t necessarily say that these were the piec,es that would be in a trade, but in addition to Boston’s interest in Paredes, Houston is intrigued by young pitchers Connelly Early (Cam Schlittler’s opponent in that fateful Wild Card Series showdown), Payton Tolle, and Mike Burrows.
10:00 AM: From last night, the Yankees were implicated in a number of rumors. The New York Post’s Joel Sherman reported the Yankees were interested in Brewer reliever Trevor Megill, coming of a 2.49-ERA campaign with Milwaukee. Sherman also reported that the Yankees were kicking the tires on reliever Brad Keller and Nationals starter MacKenzie Gore.
10:00 AM: We’ve had some more detail on the reported offer the Pirates gave Kyle Schwarber, Rosenthal adding that the offer is for $120 million over four years.
10:00 AM: The New York Post reports that the Mets are in on Michael King, with the two sides apparently having had a video meeting. A reunion between King and the Yankees has long seemed reasonable, but a switch over to Queens feels equally fitting. The Mets are reportedly loath to hand out long-term contracts to this offseason’s top starters, while King should come on a shorter deal than the likes of Dylan Cease and Framber Valdez.




