As they slip further into the cellar of the American League East, it's becoming increasingly obvious that the Boston Red Sox won't have a chance to make up for their disappointing 2025 trade deadline performance. Instead, it's becoming a virtual certainty that they'll be sellers.
There's obviously some time before that choice needs to be made — a five-series stretch at the beginning of June will pit the Sox against each of their four division rivals — but it's hard to buy into the product we've seen on the field these first two months.
But if the Red Sox do decide that selling is the best path forward, how will they pick and choose who to keep and who to deal? And, if Craig Breslow's seat is as hot as we've been led to believe, is he really the right guy to be making those calls?
"It's a tough decision to make. They've fired [Dave] Dombrowski and Chaim [Bloom] on the same timeline, where those moves were in September, after the trade deadline," Red Sox insider Chris Cotillo said on the "Monster Territory" podcast. "These are make-or-break weeks, make-or-break months for the direction of the organization."
Could the Red Sox hand the keys to another front office executive to handle the trade deadline?@ChrisCotillo explains why "it's such a tough decision to make." pic.twitter.com/Cn2sGvbB0E
— Monster Territory (@MTerritoryPod_) May 28, 2026
Craig Breslow cannot have full green light at the trade deadline to determine Red Sox's future
Like it or not, ownership sided with Breslow when they gave him the go-ahead to fire Alex Cora and his coaching staff back in April. There's at least some belief in the building that he's the one who should be making the long-term personnel decisions.
Even if that belief is faltering, though, it's going to be almost impossible for the Red Sox to change course right now. The upcoming lockout over the winter already figures to be a massive headache — blowing up the front office continuity mere months before the entire league is forced to shut down will only make it more difficult for the Sox to figure out their path.
In effect, that likely means that Breslow has until the start of the 2027 season (whenever that is) to figure his stuff out. If ownership isn't convinced he can correct his own mistakes, then they need to place strict restrictions on him at the trade deadline. He'll need to operate within a rental-only seller's mindset, much how the St. Louis Cardinals acted last year when Chaim Bloom prepared to take over for John Mozeliak.
That means Sonny Gray, Aroldis Chapman, Patrick Sandoval, Danny Coulombe, and Isiah Kiner-Falefa (if the latter three have any value) are the only names that should be discussed. Breslow shouldn't be trusted to trade an outfielder or top prospect if ownership is already developing a backup plan to replace him.
Maybe this whole conversation will be moot by July. Maybe, despite crushing injuries to Roman Anthony and Garrett Crochet, the Red Sox will survive their June gauntlet.
Or maybe this team will somehow have to navigate a pivotal trade deadline with a front office chief who may not be employed this time next year.
Add us as a preferred source on Google