Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings. Mandatory Credit: Jerome Miron-Imagn Images Jerome Miron-Imagn Images

Red Sox's Craig Breslow Hints At Culpability For Trade Deadline Failure

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Sep 24, 2025 12:00 PM ET

The trade deadline is nearly two months in the past, but it's hard to forget what the Boston Red Sox did (or more accurately, failed to do).

While every other American League contender made big moves, a long list of moves, or both, the Red Sox completed just two trades, for starting pitcher Dustin May (who has been brutal in Boston and is currently injured) and reliever Steven Matz (who has been healthy and good).

The offense, however, went completely neglected. And as Boston slogged through September with a feeble lineup that was missing two huge contributors, it's been easy to second-guess chief baseball officer Craig Breslow for not doing more.

Breslow talks failure to add offense

On Tuesday, Breslow addressed the media before the Red Sox's game in Toronto, and said with the benefit of hindsight, he was second-guessing himself for not adding another bat, too.

He did, however, add the qualifier that things might look differently had outfielders Wilyer Abreu and Roman Anthony not sustained injuries.

“It’s a tough question to answer. If we were to have known that Wily (Abreu) would be down and Roman would be down, maybe we would’ve acted differently,” Breslow said, per Tim Healey of The Boston Globe.

“But we pursued every opportunity that we had to improve the team, and you have to prioritize where you think the greatest areas of needs are. And those things clearly can change pretty quickly. But that’s the reason it’s important to have organizational depth.”

Who the Red Sox should have traded for is tougher to pin down than simply stating they should have done more.

Josh Naylor would have been a great fit at first base, but he was dealt a week before the deadline. Yandy Díaz has been incredible, but all indications are that the Rays weren't serious about dealing him. And it would have made very little sense to trade for an outfielder when the team had four very good ones healthy at the time.

If there's a lesson Breslow has to learn, however, it's that having one more big bat can make an even bigger difference in actuality than he might imagine when he's making those frantic deadline calls.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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