Why Craig Breslow's Past Trade Deadlines Suggest More of the Same for Red Sox in 2026

[Alex Mayes]

We’re less than two months away from the 2026 trade deadline and, thanks to the underperformance of the Boston Red Sox as a whole, there’s been little indication as to which path Craig Breslow is going to take as the summer market starts to heat up. Truth be told, it would be hard to figure out what Breslow was going to do even if the team wasn’t currently sitting outside the playoff picture with a losing record, despite the overall state of a very bad American League.

If the team was just a fraction better, they would be in a clear ‘buy now’ mode. If they were somehow even worse than they currently are, they would sell off their most valuable short-term commitments while trying to retool for the 2027 season and beyond. Right now, though, we’re stuck in a sort of no-man’s land. With that in mind, I wanted to dive into the past two trade deadline seasons and see if we can maybe predict what Craig Breslow is going to do as we get into hot-stove season.

Red Sox 2024 Trade Deadline Moves:

Players In: RHP Quinn Priester, RHP Luis Garcia, RHP Lucas Sims, C Danny Jansen, LHP James Paxton

Players Out: INF Moises Bolivar, INF Cutter Coffey, INF Eddison Paulino, RHP Gilberto Batista, RHP Ovis Portes, RHP Ryan Zeferjahn, RHP Yeferson Vargas, 1B Niko Kavadas, UTIL Matthew Lugo

Talk about underwhelming. Going into the 2024 trade deadline, Breslow continually spoke about the need to add a right-handed hitter to the lineup, and the team wound up with Danny Jansen who worked in a platoon role and offered very little offensively. The other additions all made various contributions; Priester made one start for the Red Sox, Garcia appeared in 15 games and posted an 8.22 ERA, Sims also appeared in 15 games with a 6.43 ERA, and Paxton only appeared in three games before landing on the injured list to end his season.

Red Sox 2025 Trade Deadline Moves:

Players In: LHP Steven Matz, RHP Dustin May

Players Out: OF James Tibbs III (acquired in the Rafael Devers deal in June of 2025), OF Zach Ehrhard, INF Blaze Jordan

The 2025 deadline haul offers even less to say than its predecessor. Matz was a solid contributor out of the bullpen in Boston but wasn’t brought back this season, and May was awful in his five starts before he ended the season on the injured list. 

Revisiting these deals likely paints a pretty clear picture of the path that Craig Breslow is likely to take as we approach the August 3 trade deadline: He’s going to try and thread the impossible needle of buying and selling at the same time, as it seems that has been his modus operandi since he arrived in Boston. The biggest difference between the last two trade deadlines and this year are that the Red Sox are in a drastically different place in 2026.

The team had a couple of obvious needs in 2025, but they were clearly in the midst of a playoff push thanks to a 10-game winning streak as they headed into the All-Star break. In 2024, there was reason to believe they could be competitive if everything broke in their favor. This year, though, one or two trades likely won’t make a difference for this team even in the short term. ESPN’s Buster Olney went on record on June 3 saying that he’s heard from his sources that the Red Sox are “aggressively looking for a right-handed hitter and signaling to the industry, look, we're willing to take on money.” That’s all well and good, but Breslow has shown that he’s more in the business of saving money in trades that welcoming it in. Just look at the Rafael Devers deal. There is a fairly lengthy list of right-handed hitters that are carrying bad contracts that Breslow could be looking at here, but adding that one piece won’t fix the inability to play quality baseball at home. If a deal for an impact right-handed hitter is on the table, does anyone really trust Breslow to get it done? It’s unlikely at this point.

It feels like Breslow is approaching this trade deadline under the impression that his decisions may decide his fate in Boston. There has been more and more reports that members of the ownership group have grown unhappy with the hyper-focused analytical approach, and you have to assume that the length of leash ownership has given him is drastically different than previous seasons. With that in mind, expect Breslow to sell off short-term commitments that the team currently has while attempting to deal from the farm system to add a right-handed bat somewhere in the lineup. From the past two deadlines, we can see that Breslow tends to deal from positions of strength when making deals. Right now, that involves anyone who plays in the outfield, though perhaps the impending lockout may put an additional premium on prospects with years of team control.

Simply put, Craig Breslow has a tall task in front of him by trying to both buy and sell at the deadline. That same mentality likely played a large role in costing Chaim Bloom his job in 2023, so Breslow has to be hoping that a similar fate isn’t in store for him in 2026. If he’s being trusted to navigate the trade deadline, and all signs point to that being the case, then he needs to be decisive and take advantage of however much leeway John Henry and company are giving him.

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