The Boston Red Sox appear poised to make a splash in significant fashion at the trade deadline.
Whether you’ve followed that path through the big-name national reporters or the latest round of reports from the local beat, it feels like every update indicates that Boston is in the mix for the most impactful names on the market this time around.
That should be the mission, and completing one of those deals for an impact shortstop among other interests would be a massive shot in the arm for a Red Sox
team with plenty momentum as it heads into the final two months of the season.
Craig Breslow is busy, already making the deal for Curtis Mead that was the right move, even after the ill-timed injury of the new infielder on Tuesday. The Red Sox seem far from done in navigating the market before Monday’s 6 p.m. ET deadline, though Breslow has as much to prove in this cycle as any executive in baseball.
His job looks safe for the time-being amid the remarkable turnaround that’s seen this ballclub rejoin the postseason conversation. With that said, arguably Breslow’s greatest shortcomings have come in his first two trade deadlines as Boston’s chief baseball officer.
If you want to play with the letter of the law, Breslow and the Red Sox did “buy” at the trade deadline in the last two seasons. They bought at positions of need, but the quality and the impact of those players does diservice to the term “buyer.” Rather, Boston “added” with cheap reinforcements to the roster that disrespected the production of the clubhouse and cost the team down the stretch.
For reference, the Red Sox did “add” a starting pitcher, a right-handed bat and two relievers at the 2024 deadline. But how much did James Paxton (injured shortly after) and Danny Jansen (backup catcher) move the needle for that club that played scorching ball into the All-Star break and faltered after? How about the measly acquisitions of Lucas Sims and Luis Garcia, who simply filled spots in the bullpen and only cost Breslow a slew of prospects who would not have been protected in that offseason’s Rule 5 Draft anyways?
The lackluster additions failed to boost the club and the Red Sox missed the playoffs for a third straight year at 81-81. In 2025, Boston overcame another deadline failure to make the postseason, but the series loss to the Yankees highlighted the misses, headlined by the Joe Ryan whiff, paired with the minimal-to-negative impact of Dustin May and Steven Matz.
To be fair, the Red Sox have a presidential term’s worth of failed deadlines, which go back beyond Breslow to Chaim Bloom’s regime. Still, Boston cannot afford another annual meltdown of transactions. The 2026 ballclub showed themselves worthy of strengthening the roster. It obviously takes two to tango and prices are high for talent this time of year for obvious reasons. Breslow and the front office need to show an ability to push those aside and get deals done between now and Monday evening.
Breslow deserves plenty of credit for his offseason additions early in his tenure. He brought in three All-Stars for the 2025 club in Alex Bregman, Garrett Crochet (extended) and Aroldis Chapman (extended, plus the solid season of Carlos Narvaez. This past winter was no different given how strongly Willson Contreras, Sonny Gray and Ranger Suarez have shaped the team’s current playoff aspirations. Those all deserve gold stars, but Breslow’s run of activity in-season to this point strongly deserves the label of disastrous.
Pressure is a privilege. Breslow can make that go away with a deadline of real “buying” rather than fringe “additions.” We’ll revisit that contrast by early next week.
