The pressure on Red Sox president of baseball operations Craig Breslow is starting to build. Boston has struggled to get deals done, and patience inside the organization may be wearing thin. That idea gained attention this week when Red Sox podcaster Terry Cushman Jr. suggested Breslow could be in trouble. The team has yet to close a deal for Alex Bregman, and another top target, Pete Alonso, has already signed elsewhere. As missed chances add up, the focus on Boston’s front office continues to grow.

Now Cushman is back again, and his tone is even sharper. He’s now doubling down on the idea that Breslow’s firing isn’t a matter of if, but when. That said, Cushman did leave the door slightly open, suggesting there are still a few moves Breslow could make that might help him save face before the inevitable happens!

“And so what I’m thinking is, if you’re going to get fired anyway, just resign. Some people would look at that as a cowardly move, but I think in his case, given his circumstances, you know, with the stuff that is within his control and then a lot of stuff that’s beyond his control, I think it’s more of a power move,” Cushman shared via X.

So what are the actual chances that Craig Breslow gets fired? Because outside of Cushman, there’s been no official word or concrete signal from the Red Sox themselves. Still, the situation feels like it’s drifting in that direction!

Remember back in June, Bleacher Report’s Zachary D. Rymer said Breslow wasn’t on the hot seat at all? At the time, that made sense. The Red Sox were being linked to names like Alex Bregman and Garrett Crochet, and there was optimism that big moves were coming. Fast-forward to now, and the picture looks very different.

Boston has missed out on players like Kyle Schwarber and Pete Alonso. Bregman still hasn’t recommitted, and while the team has added pieces like Sonny Gray and Johan Oviedo, fans are still waiting on that impact bat Breslow keeps teasing. Add in the fact that the Red Sox haven’t won a World Series since 2018, and the patience around the front office is clearly wearing thin.

So, from Cushman’s point of view, ownership has little reason not to move on from Breslow at this stage. “I don’t think Breslow has made the most of the resources he does have. He’s lost a lot of trades. He’s mishandled both trade deadlines.”

His one potential off-ramp, Cushman suggests, would be resigning before being shown the door. That would allow Breslow to control the narrative, making it seem like a mutual parting or a personal decision, rather than the organization deciding it’s done with him. “So it would be a power move if he were to just flip Henry and Kennedy the bird and say, I’m done. I can’t work with these circumstances and just exit on your own terms,” Cushman suggests.

A similar situation happened in San Diego, where A.J. Preller came under heavy pressure after the Padres spent big but did not get the results they expected. Fans and media quickly turned their focus to the front office and questioned the team’s direction. Even though Preller kept his job, it showed how quickly trust can fade when expectations aren’t met. Breslow’s situation is different, but the pressure feels the same, with growing questions about whether ownership still believes in the plan.

Bottom line: Cushman sounds convinced that Breslow’s time in Boston is coming to an end. The only real question left is whether Red Sox ownership sees it the same way. Or if they’re still willing to give him one last chance to change the story.

Breslow still made a few marks

While the Red Sox couldn’t be any extraordinary under Craig Breslow when it comes to trade deals, he still had a few marks in the team. The first being business economics.

Back in March, Forbes reported that Boston pulled in about $574 million in revenue in 2024. That too after finishing with an 81–81 record. That figure ranked fourth in all of baseball, behind only the Dodgers, Yankees, and Cubs. However, those three teams spent far more than the Sox, especially the Dodgers and Yankees. So, by not splashing money in the offseason, Boston actually walked away with the biggest profit in the league!

So the big question is whether Red Sox ownership is actually unhappy with Craig Breslow. Financially, the team is thriving. The offseason isn’t over yet, and if Breslow manages to land a marquee name like Kyle Tucker, Bo Bichette, or Cody Bellinger, the entire narrative could flip overnight.

In that sense, just like the talk around his potential firing, the idea of Breslow landing a major star might simply be a matter of timing. This might only decide Breslow’s tenure with the Red Sox!