Once thought to be surefire sellers, the Boston Red Sox have won 20 of their last 23 games and could now find themselves as one of the biggest players in search of upgrades ahead of the Aug. 3 trade deadline. With a farm system on the rise and a stable of young major league arms, Chief Baseball Officer Craig Breslow certainly has the ammo to go out and make a major splash. The only question is, how aggressive does the third-year head of baseball operations want to get? 

Breslow has done what he can to temper expectations leading into the trade deadline, telling MassLive.com's Chris Cotillo on Sunday that he doesn't think the lengthy winning streak should determine exactly what the team does ahead of the trade deadline, but that the team has put itself in a good position. 

Breslow cited the uncertainty about who might be available, given the crowded playoff picture in both the American and National Leagues, as the reason for his ambiguous answer.

While Breslow himself was unwilling to commit to a deadline path for the Red Sox, one prominent baseball insider, ESPN's Jeff Passan, is predicting an aggressive deadline for Breslow. 

"When you can add talent, you add talent," Passan told the Pat McAfee Show on Tuesday. "There are names being tossed around that would make a lot of sense for the Red Sox... I think the Red Sox are gonna try and be aggressive, and I don't blame them... When you rescue your season from the depths and doldrums where they were for the first 80-something games, you just have to go and do it," he continued. 

Among the names Passan mentions as being of interest to the Red Sox are a trio of controllable shortstops: Los Angeles Angels' Zach Neto, Houston Astros' Jeremy Pena, and CJ Abrams of the Washington Nationals. While Breslow might not be willing to commit major assets to acquire a rental piece in a season that still hangs in the balance, Neto, Pena, and Abram all have multiple years of team control, making them a solution for 2026 and beyond.

Passan is also correct in his assertion that Breslow should act aggressively after his team worked its way back from the basement to sole possession of the third wild-card spot in the American League. The Red Sox boast one of the best rotations in baseball, but a lineup that, in Breslow's own words, has "struggled to score runs at times." 

If a pitching staff that is more than capable of making a deep playoff run is not one that's worth investing in, then it's fair to question when, if ever, Breslow would be willing to push his chips in the middle. 

While shortstop doesn't jump out as an immediate need for Boston, the 2026 season has left more questions than answers for the Red Sox at the most important position in the infield. 

Former top prospect Marcelo Mayer was long considered the shortstop of the future in Boston; however, the 23-year-old struggled to a .222/.282/.312/.594 slash line in 70 games before landing on the 15-day injured list with a stress reaction in his left forearm. 

Also, veteran Trevor Story was among the worst hitters in baseball, hitting just .206/.244/.303/.547 in 41 innings before undergoing surgery for a sports hernia on May 22. Along with Story's struggles at the plate, the 33-year-old has just one-year remaining on the six-year, $140-million deal he signed ahead of the 2022 season. 

Boston also has its top-rated prospect, shortstop Franklin Arias, who could fill the void at short; however, as Mayer has shown, prospects, no matter how highly regarded they might be, are anything but a sure thing. The 20-year-old Arias could be used as the centerpiece to land one of the established major leaguers.

The acquisition of Pena, Neto, or Abrams would offer Boston a proven, productive major leaguer at either middle infield position for at least the foreseeable future. 

The MLB Trade Deadline is Aug. 3 at 6:00 p.m. ET. 

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