Red Sox 2025 Winter Meetings Primer: Rumors, Schedules, and Craig Breslow's Stomping Grounds

[Brandon Glick]

The 2025 Winter Meetings are nearly upon us! The annual four-day event begins officially on December 8 in Orlando, Flordia, though most teams will begin arriving by Sunday, Dec. 7.

There's a lot that tends to go down at the Meetings every year, so let's break down the schedule, and the biggest rumors and noise surrounding the Boston Red Sox heading into the offseason's biggest event.

NOTE: The Red Sox completed their Jhostynxon Garcia trade with the Pirates shortly before this article was set to publish.

---

Red Sox's Offseason Thus Far

The big move Boston has made was the acquisition of Sonny Gray in a trade with the St. Louis Cardinals. The 36-year-old right-hander should be a perfect fit in the middle of Alex Cora' rotation alongside Garrett Crochet and Brayan Bello.

Otherwise, the team has focused on protecting prospects and preparing the 40-man roster for a busy offseason. Some notable non-tenders (Nathaniel Lowe) and minor trades (Luke Heyman, Ronny Hernandez) clog up the team's transaction log, but for the most part, this is still largely the same roster the team had when the 2025 season ended. The Red Sox's notable free agents include Alex Bregman, Lucas Giolito, and Steven Matz.

In terms of previous Winter Meetings, the Sox brought in both Chris Sale (2016) and Crochet (2024) at the event in past years. This is perhaps the single-best chance to make a trade on the league calendar thanks to the proximity of every major front office executive, though Boston may focus on free agents this time around after trading for Gray.

---

2025 Winter Meeting Schedule

Location: Orlando, FL

December 8 marks the first official day of the meetings, and it should be a busy one. There's already been a number of notable moves made this offseason, from the Dylan Cease signing to the New York Mets and Texas Rangers' blockbuster trade involving Marcus Semien and Brandon Nimmo. The big expectation is that at least two of the big three Japanese stars (Munetaka Murakami, Kazuma Okamoto, and Tatsuya Imai) will sign at the Meetings, as their posting windows will close within the next month and change.

December 9 will be when the league's annual MLB Draft Lottery takes place, though by virtue of making the playoffs in 2025, the Red Sox won't find themselves in contention for the No. 1 overall pick.

December 10 will feature the Rule 5 Draft, in which teams can selected unprotected prospects from other organizations. In order to keep drafted players, teams must keep them on the active 26-man roster (or the 60-day IL) throughout the remainder of the following season; otherwise, the prospects' original team can take them back. In terms of recent Rule 5 picks, the Red Sox have a few members of their bullpen (Justin Slaten, Garrett Whitlock) who stand out as excellent selections.

The Winter Meetings will officially end on December 11, though most teams will depart from Orlando before the finish line is crossed. Still, the groundwork laid in Florida will lead to a cascade of signings and trades through the New Year.

---

Red Sox Winter Meetings Rumor Roundup

Sonny Gray won't be the only starting pitching addition.
This is something we've believed since the moment the Gray trade was made, but at this point, it seems to be a lock. The Red Sox made sure the Cardinals ate a bunch of salary so they could maintain flexibility throughout the remainder of the offseason, be it via more trades or a blockbuster free agent or two. My money is still on Freddy Peralta, but Tatsuya Imai remains a very popular name that continues to pop up in rumors. I also wouldn't be stunned if the team finally leverages its outfield depth to swing a trade with Jerry Dipoto and the Mariners, who have seemingly soured on Victor Robles in right field.

Will Sonny Gray be extended?
From what I've seen, this topic hasn't come up much, but it is a pressing matter. Gray, 36, is a free agent after the 2026 season, assuming his $30 million mutual option is declined in favor of a $10 million buyout. With the 2027 lockout looming, Gray would be wise to secure one last big contract, though I don't expect the Red Sox to be the ones to pay it. Gray was acquired as a true one-year rental, and I'd imagine Craig Breslow has every intention of maintaining some payroll and roster flexibility for next offseason.

Are the Red Sox prioritizing a reliever?
Aroldis Chapman was utterly brilliant in 2025, and set-up man Garrett Whitlock wasn't far behind. Yet, Chapman is 37 and had a long run of mediocrity before his maiden campaign in Boston, and Whitlock can become a free agent next year if the team declines his option. Thus, it shouldn't be a surprise that the Red Sox have been poking around the bullpen market in free agency. And I'm not talking about a small play like a reunion with Steven Matz — I mean that there's real smoke on the reliever fire, whether it be a more cost-effective option like Pete Fairbanks or a true upper-echelon closer like Edwin Diaz. I'm under the impression the latter will only happen if the team swings and misses on all of its primary starting pitcher targets, but pairing Chapman and Whitlock up with another elite leverage arm could shorten a lot of games in 2026.

What on earth is happening at first base?
Truthfully, I don't know, and I'm not sure anyone does. Triston Casas has more fans than detractors in the organization, but you simply can't rely on him to stay healthy at this point. I'm pretty sure the Sox don't want Murakami -- his strikeout issues are a real concern for MLB teams -- and Okamoto is probably going to exit their "comfortable" price range. Power is a necessity, so someone like Luis Arraez is off the table as a reclamation project. This truly might be a spot where a trade has to happen, unless the Red Sox completely pull a 180 on their modus operandi and sign an aging Pete Alonso to a long-term contract.

View full article

[harmony]

In the section on potential starting pitcher additions: "the Mariners, who have seemingly soured on Victor Robles in right field."

Seattle is unlikely to trade from its starting rotation unless a trade partner is willing to assume Luis Castillo's entire contract.

The Mariners already return three right fielders who in the past two years have posted seasons of 3.2 bWAR in 137 games (Luke Raley 2024), 3.1 bWAR in 77 games (Victor Robles 2024) and 1.6 bWAR in 82 games (Dominic Canzone 2025).

With All Stars Julio Rodriguez and Randy Arozarena, the outfield is not among Seattle's most pressing needs this offseason.

[Brandon Glick]

24 minutes ago, harmony said:

In the section on potential starting pitcher additions: "the Mariners, who have seemingly soured on Victor Robles in right field."

Seattle is unlikely to trade from its starting rotation unless a trade partner is willing to assume Luis Castillo's entire contract.

The Mariners already return three right fielders who in the past two years have posted seasons of 3.2 bWAR in 137 games (Luke Raley 2024), 3.1 bWAR in 77 games (Victor Robles 2024) and 1.6 bWAR in 82 games (Dominic Canzone 2025).

With All Stars Julio Rodriguez and Randy Arozarena, the outfield is not among Seattle's most pressing needs this offseason.

This is an excellent observation, and exactly why I called the Mariners out by name in this section (as opposed to, say, the Royals, who very clearly have needs in the outfield).

The buzz in Mariner Land is they don't want Robles as anything more than a 4th outfielder. He was awful in 2025 and really hasn't been productive in the big leagues outside of that 2024 Linsanity run (and the 2019 season). Raley has never been much more than a utility corner infielder/outfielder, and his bat fell off a cliff in 2025 (91 wRC+). Canzone is the wild card; if the Mariners are willing to trust him with that third spot next to Arozarena and Rodriguez, that could take them out of the outfield market.

However, Arozarena is a free agent after 2026. And they need to resupply some power to the lineup after losing Suarez & Polanco. I'm sure they'd love a star third baseman (Alex Bregman?), but they need to be cost-conscious considering their payroll is already near last year's record high (for them).

They could very easily trade for a Duran/Abreu to fill that right field hole while having them around long-ish term to help backfill for Arozarena's absence. And I think you're off the mark with the Castillo comment. George Kirby could easily be expendable after a relatively mediocre season, especially if they want to give Logan Evans or Emerson Hancock more MLB run.