It just feels like nothing is going right for the Red Sox, and especially not for president Craig Breslow. After getting bounced by the Yankees in this year’s wild series, fans were hoping the offseason would bring some kind of reset. Even Breslow had talked up the plan earlier, saying the team had “compelling opportunities” ahead. And that while they’re trying to contend now, they’re also keeping an eye on the future.

But so far, the results haven’t matched the talk. The team still hasn’t landed Alex Bregman, and another big target, Pete Alonso, ended up signing with the Orioles. Now, that is enough for Red Sox podcaster Terry Cushman Jr. to suggest this might be Breslow’s last run with the team.

“I mean, how many times did he shoot himself in the foot yesterday by saying Alonso’s not the right guy? You know, they don’t want to give him that many years… And as I said last night on the podcast, he doesn’t even know how to trade Jarren Duran. He doesn’t know how to execute a trade like that to fill a need… So, I guess to wrap up, I think this is it. I think this is one final sh*tshow for him, and I think the team’s going to be forced to move on.”

Cushman is certain that Breslow is on his last leg with the Red Sox and that owner John Henry would be forced to leave past him.

But why is Breslow catching so much heat?

Well, if you remember, last offseason actually went pretty well for the Red Sox. Breslow added Justin Wilson, who became a steady arm in the bullpen. Then, Aroldis Chapman turned in a dominant All-Star year as the closer. He also pulled off a trade for Garrett Crochet, who ended up finishing second in the AL Cy Young race.

Still, the season didn’t live up to expectations, and this winter has been frustrating!

The Red Sox have missed out on players like Kyle Schwarber and Pete Alonso, and Bregman hasn’t recommitted. Sure, they’ve made some moves, bringing in Sonny Gray and Johan Oviedo. However, people are waiting for Breslow to finally land the big bat he keeps hinting at. Remember, the clock is ticking!

That’s why Cushman argues that Craig Breslow hasn’t sealed a signature deal nor filled the roster gaps by moving players like Jarren Duran. So why would the front office stick with him?

But the offseason isn’t over yet, and there are still a few major free agents available. So, it might be a little too early to make any final judgments.

What went right for Breslow with the Red Sox?

Honestly, it’s not accurate to say Craig Breslow hasn’t made an impact with the Red Sox. Their farm system is proof that he has. Reportedly, at the start of the 2025 season, the team had three of MLB’s top 12 prospects — Roman Anthony, Kristian Campbell, and Marcelo Mayer. All of them have already made the jump to the majors.

The Red Sox are one of the few teams that not only promote their prospects aggressively but also see those players succeed. Roman Anthony, for example, hit eight HRs and batted .292 in his rookie year.

Moreover, players like Justin Gonzales are the latest examples of the international scouting department doing strong work. Pitching development has also taken a big step forward, with arms like Tolle, Brandon Clarke, and Connelly Early!

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So while Breslow hasn’t delivered the kind of flashy, star-studded offseason the Dodgers are known for, he has built a farm system that’s deep and dependable. Still, at the end of the day, results matter. And fans want to see what moves he’ll make to help this team finally push deep into October.