State of the Sox: Trade deadline will help determine Craig Breslow’s legacy

· Yahoo Sports

If we’ve learned anything in the last month, it’s that things can change in a hurry.

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It wasn’t long ago that there was speculation that Craig Breslow would not survive a season in which the Red Sox failed to make the postseason.

But the team’s U-turn, taking them from 14 games under .500 to the second wild card team, one close enough to breathe down the Yankees’ neck, has completely altered the picture.

There’s still two months remaining in the regular season, and given that the Red Sox are currently favored to reach the playoffs — calculated at 69 percent before Thursday’s win – it should stand to reason that Breslow’s job appears safe.

Back in June, it seemed as if the trade deadline was going to serve as a referendum on Breslow’s job security — play in October and he was likely safe; fail to reach the postseason and it was probable he’d be gone. That’s not the question any more.

There is, however, still plenty on the line by Monday evening and that’s Breslow’s legacy.

Since being named chief baseball officer in the winter of 2023, Breslow has overseen two and a half seasons. His work in the offseason has generally been very good.

Last winter alone, Breslow acquired, either through trade or free agency: Sonny Gray, Ranger Suarez, Willson Contreras, Caleb Durbin and Jake Bennett.

The offseason before, he added Garrett Crochet, Aroldis Chapman and, however briefly, Alex Bregman.

Full marks there. Breslow overhauled the starting rotation, the back of the bullpen, and though a case could be made that he should have done more to boost the offense, the acquisition of Contreras has had a major impact on the 2026 team with two more years of control remaining.

But it’s one thing to make successful trades (and signings) in the offseason, and it’s another to make them at the deadline. And it’s there that Breslow needs to improve.

Improving the roster in November, December and January allows for more leeway. There’s plenty of time to wait out the free agent market and react to what other teams have done. The deadline is nowhere near as forgiving: most moves get done in the final 96 hours, and timing is everything. It requires quick adjustments, good instincts and the ability to act decisively within a brief window.

To date, Breslow hasn’t shown himself capable of doing that.

Breslow’s first deadline really shouldn’t count against him. At the time, the Red Sox were barely holding on to the third wild card. There was no consensus that the team was worst investing, and so Breslow’s list of pickups were mostly depth moves: Danny Jansen, Lucas Sims, Luis Garcia. Nobody expected that group to move the needle and they didn’t — by the first week of September, they had dipped to .500 and that’s where they finished.

Last year, however, was different. The Red Sox were better positioned, and yet Breslow failed to make any significant moves. Starter Dustin May performed poorly and Steven Matz was merely an effective middle reliever.

This summer, the pressure is on. The team’s climb back into contention has the feel of legitimacy and the American League lacks a dominant team. If there were ever a year in which a wild card team could make a true run for the pennant, it’s this one.

First, however, they need help.

To his credit, Breslow struck first last weekend, sending Connelly Early to Washington for infielder Curtis Mead. You can argue that Breslow gave up more than he should have, but you have to admire his aggressiveness to fill an obvious need.

We know what happened next: two plate appearances into his Red Sox tenure, Mead was struck on the left wrist by a 95 mph fastball, resulting in a broken wrist. The hope is he’ll return in late September, but that’s no guarantee.

Breslow doesn’t deserve blame for a freak injury, but the cold hard truth is that, for the time being, the Red Sox are down one valuable trade chip (Early) and without the services of the player for whom he was traded. In a best case scenario, they’re right back where they started.

It’s doubtful that Breslow is done. By all accounts, the Red Sox continue to have trade talks in search of a shortstop or a catcher, and perhaps some additional pitching, too. The majority of the people in the game expect the Red Sox to be active, even post-Mead.

What Breslow does in the next four days could well define his tenure in Boston. The proper trade(s) could further lift the Red Sox’ playoff chances and position them for a deep October run.

Anything less, however, will further cement the notion that Breslow never did enough to give his teams an improved chance by his actions at the deadline.

Every successful front office executive in Boston has succeeded at crunch time. Theo Epstein had his missteps (Eric Gagne, anyone?), but he also landed Orlando Cabrera, Dave Roberts and Doug Mientkiewicz in one fell swoop in 2004, and without them, the Red Sox don’t win the World Series that fall.

Now it’s Breslow’s turn to prove that his smart acquisitions aren’t limited only to the offseason.

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