With external noise about the security of Boston Red Sox Chief Baseball Officer Craig Breslow’s job growing louder, a source within the organization told Tim Healey of the Boston Globe that the team is not considering making a change. With Boston trending towards being sellers with each passing day, it looks more and more like the August 3 trade deadline will be a pivotal moment in this era of Red Sox baseball as they look to retool themselves into the World Series contenders they entered the season thinking they were. Is the decision to keep Breslow around to make those moves the right one, though? 

Since his hire ahead of the 2024 season, Breslow has handled the last two trade deadlines for Boston, where his track record is…not great, to put it kindly. 

With the Red Sox sitting at 56-51 and 2.5 games back of the final wild card spot in the American League, Breslow took a quantity-over-quality approach to the trade deadline. Making four deals to improve the Boston roster, adding starter James Paxton, catcher Danny Jansen, and relievers Lucas Sims and Luis Garcia for the playoff push. None of whom made a major impact during their time in Boston. 

Paxton appeared in just three games for Boston, posting a 4.09 ERA across 11 innings of work before suffering a partial tear in his right calf, ending his season and career. While Sims and Garcia were wildly ineffective, combining for a 7.26 ERA in 29.1 innings pitched. 

Despite the injury to Paxton and the ineffectiveness of Sims and Garcia, the acquisition of Jansen was by far Breslow’s biggest miss of the season. After shoulder surgery ended shortstop Trevor Story’s season, Boston was in desperate need of a right-handed bat for the heart of the lineup, choosing the then 29-year-old catcher to fill that void. Jansen appeared in 30 games for the Red Sox, hitting just .188/.323/.300. 

Breslow also acquired former first-round pick Quinn Presiter in a prospect swap with the Pittsburgh Pirates in exchange for second baseman Nick Yorke. Preiester made one appearance for Boston, a five-inning start in which the then 23-year-old allowed one run on four hits while striking out two and walking one. It would be the only appearance Preister made in Boston, as he was dealt to Milwaukee in an offseason deal in exchange for prospects Yophery Rodriguez, John Holobetz, and a competitive balance selection in the 2025 draft, which was used on pitcher Marcus Phillips. 

While Breslow did not give up any major pieces of Boston’s future, the relatively quiet deadline landed the Red Sox on The Athletic’s ‘snoozer’ list. All in all, the Red Sox’ acquisitions combined for a -0.7 bWAR as Boston finished the regular season 25-30, missing the playoffs for the third consecutive season. 

Breslow and the Red Sox entered the 2025 deadline at 59-51 and in firm control of the second Wild Card position in the American League. They did, however, have two clear needs: replace the production that was lost in the June 2025 deal that sent Rafael Devers to San Francisco and find a bona fide number two to pitch behind Garrett Crochet.

After a day full of rumors linking Boston to Minnesota Twins ace Joe Ryan, the two sides were unable to come to terms on a deal. The inability to land Ryan left Breslow to make a last-minute pivot to Los Angeles Dodgers starter Dustin May, who was acquired in exchange for former first-round pick and key piece of the Devers trade, James Tibbs III. May made six appearances for Boston, allowing 17 earned runs on 35 hits over 28.1 innings before missing the Wild Card series in New York with right elbow neuritis. A far cry from the Robin to Crochet's Batman that the team was looking for.

To make matters worse for Breslow, after hitting just .207/.319/.267/.586 in 30 games in the Red Sox organization, Tibbs joined the Dodgers farm system and immediately took a step forward, hitting .282/.401/.559/.960 in 117 games since the trade. 

Boston also acquired left-handed reliever Steven Matz in a deal with the St. Louis Cardinals for first base prospect Blaze Jordan. Matz performed well in his short stint with the Red Sox, posting a 2.08 ERA in 21 appearances for Boston before leaving for Tampa in free agency. 

What was most puzzling about Breslow's deadline, though, was the lack of offense added. Ultimately, the Red Sox made the playoffs in the final wild card spot, losing to the Yankees in three games, thanks to the lack of a true No. 2 behind Crochet and an offense that struggled to score without Devers production. 

Whether or not you think the Red Sox should be buyers or sellers, it's fair to question whether Breslow has the ability to make the necessary moves to retool Boston's roster back into the World Series contenders they painted themselves as entering the 2026 season. 

Across two deadlines at the helm of the Red Sox, Breslow has added six players who combined for -0.5 bWAR as both teams limped to the finish line, finishing 55-52 in the 107 games after the deadline. 

Boston has no shortage of movable assets should they choose to be sellers at the August 3 deadline. According to USA Today's Bob Nightengale, Aroldis Chapman is the top reliever on every contenders list. While fellow high leverage arms Garrett Whitlock and Justin Slaten are also generating interest. 

However, there is not much in Breslow's history of deadline deals to signal he is capable of making the right decisions, both about whom to sell and whom to acquire. Fenway Sports Group's decision to stick with Breslow could prove costly for years to come.

The Major League Baseball Trade Deadline is set for 6:00 p.m. ET. on August 3. 

The Red Sox will take on the Tampa Bay Rays in game two of a three-game series on Tuesday night. Payton Tolle (3-2, 2.28 ERA) will get the start for Boston opposite Nick Martinez (5-2, 2.29 ERA) for Tampa. First pitch from Tropicana Field set for 6:40 p.m. ET. 

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