Monday’s MLB trade deadline has come and gone, and the Boston Red Sox were among the most active teams across the entire league, adding five players in four deals to their major league roster. While the Boston roster got much better with the additions of Adley Rutschman, Erik Miller, Eli White and Jake Rogers, there were several current members of the Red Sox organization who were big winners on their active deadline day as well.   

There may not be a single person across Major League Baseball who has had a better last month than Boston’s third-year Chief Baseball Officer. His team went from the basement of the American League to the hottest team in baseball, thanks to the winningest month of baseball in franchise history. 

Breslow entered Monday’s deadline looking to learn from his first two deadlines, which went about as poorly as they possibly could have, adding no real players of significance while his teams limped to disappointing finishes. 

However, Breslow passed his deadline test with flying colors. While there are still questions that remain about the deadline, he acted with conviction and took the big swing that fans were begging him to, adding a true star player at a premium position in Rutschman. 

In the immediate aftermath of the deadline, there is no bigger winner in Boston, and maybe across all of baseball, than Craig Breslow.

It’s no secret that the Red Sox were aggressively pursuing a long-term solution at shortstop, being linked to nearly every name on or off the market at the position, including Zach Neto, CJ Abrams, Elly De La Cruz, and Jeremy Pena, just to name a few. 

Ultimately, the price was too rich for Breslow to meet the ask to obtain one of those names, leaving the Red Sox to patch things together at the position while top prospect Franklin Arias continues his development in Triple-A. 

Breslow’s failure to land a shortstop, paired with the trade that sent former top prospect Marcelo Mayer to San Francisco, has completely cleared the runway for Story to reclaim his position upon his return from sports hernia surgery.

Another point of emphasis for Breslow ahead of the deadline that was not acquired was starting pitching depth to alleviate the workload on a pair of rookie lefties, Payton Tolle and Jake Bennett, who have both surpassed their career highs in innings pitched. 

Enter Brayan Bello, who has been one of the best relievers in baseball after struggling mightily during his time as a starter. In 42 innings of relief, the 28-year-old has posted a 0.64 ERA, the lowest of any reliever with at least 35 innings of work. 

With injured starters Garrett Crochet, Kutter Crawford and Tanner Houck’s status for the 2026 season remaining up in the air, Breslow pointed to Bello as someone who could help alleviate some innings on the starters when he met with the media on Monday night. 

“We’re mindful of the workload our starting pitchers are taking on,” he said. “We feel like we do have some depth, whether that's currently in the big leagues, you see the job Bello has done pitching out of the pen, and also in Triple-A,” he continued.

Once thought of as a completely depreciated asset, Bello has found himself in a position to be an incredibly valuable member of the Boston pitching staff for the stretch run.  

Whether or not Bello or Story can capitalize on their newfound opportunities and salvage what was thought to be a lost season remains to be seen, but they are comfortably the two biggest winners after Breslow’s active day. 

Boston will look to make it seven straight wins and nine straight series wins on Wednesday night, taking on the Chicago White Sox in game two of a three-game set from Fenway Park. Sonny Gray (13-2, 2.93 ERA) will get the start for the Red Sox opposite Sean Burke (7-5, 3.04 ERA) for the White Sox. First pitch is set for 7:10 p.m. ET. 

Zach Coe and David Azer broke down all of the Red Sox moves from an exciting trade deadline day across all of baseball in the latest episode of the 'Entering Kenmore' Podcast. Check it out wherever you get your podcasts or on YouTube!