To buy or sell? That question looms once again for the Red Sox

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It’s trade season in MLB, where teams feel whether they are competitive enough to be bought into the postseason or are too low on the ladder to do anything but sell assets and look to the future.

But for the Red Sox, 2026 is starting to present a bit of a dilemma, and one that’s all too familiar at the time. Boston is once again stuck in the middle, and it’s unclear exactly where it stands.

A month ago, this seemed like an easy decision. Boston’s best players were dropping like flies, the team was well below .500, and it was widely reported that they would sell anyone worthy of future returns.

Guys like Aroldis Chapman, Garrett Whitlock, Justin Slaten, and even Sonny Gray seemed to be available at the right price.

So the fact that this is even a decision is a testament to how impressive the Red Sox’s rebound has been. They are on a seven-game winning streak, and are less than two games away from last place in the American League.

Now it makes you wonder, if Boston looks this good without superstar Garrett Crochet, rising stars Romain Anthony and Marcelo Maier, and a veteran midfielder like Trevor Story, is it worth it to keep those assets and try to acquire more talent to make a late push?

This question must be answered, and answered decisively, because Boston has been down this road several times before with disappointing results.

And at the 2024 and 2025 deadline, Boston doesn’t appear to have taken a firm stance on whether they’re good enough to compete. So they didn’t really buy, but they didn’t sell either.

This choice does not help them now or in the future.

So Breslow and the Red Sox must look at this latest part of baseball with wary eyes. Is this a flash in the pan? Or a sign of what Boston could become this season if management buys into this turnaround?

And if Breslow is truly fighting to keep his job — reports vary on his status in the organization — he will likely do everything he can to prove that the roster he has built this offseason can compete. Things are just starting to go downhill in that regard.

His shooting depth has been essential and a huge strength for 2026. Wilson Contreras is one of Boston’s most effective offensive assets. Caleb Durbin is experiencing a major resurgence at third base, posting similar statistics to Alex Bregman, who Breslow swung and missed when evaluating his free agency market this offseason.

There is a world where the Red Sox can improve at the deadline and be a sneaky playoff contender. There is also a world where they view 2026 as a bad year and try to bring back some young talent for the coming years.

The only mistake Boston can make is letting another deadline come and go without them deciding which of these two worlds they want to live in.