Red Sox May Be MLB’s Biggest Wild Card at the 2026 Trade Deadline

The Boston Red Sox are going to have some intriguing decisions to make ahead of the trade deadline.

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

One thing that Boston Red Sox chief baseball officer Craig Breslow has shown is that he's not afraid to make a splash in the trade market.

We've seen Breslow trade big-name guys away like, for example, Rafael Devers. Also, we've seen Boston make a handful of additions via the trade market over the last few years including Garrett Crochet, Willson Contreras, and Sonny Gray, among others.

Between now and the 2026 Major League Baseball trade deadline on Aug. 3, the Red Sox are going to be under a microscope. The Red Sox have a decision-maker who isn't afraid to make deals — both big and small — and the Red Sox are seemingly at a crossroads. The American League is weak right now, but the Red Sox have still struggled in comparison. Boston is 20-27 on the season so far. There's time to make up ground in the standings and look to add pieces. If the club struggles, the Red Sox have pieces that would bring back solid returns in the trade market, like Jarren Duran or Gray.

What Will Boston Do?

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

At this point, Boston could go in either direction. That's the perception out there around the team right now as well. The Athletic's Ken Rosenthal was asked about the Red Sox on Monday and shared that he expects that the team will "remain intact" for the foreseeable future because the American League is weak.

On Tuesday, The Athletic's Jim Bowden shared a column in which he took a look at each time and evaluated where each team stands with their trade deadline outlook. For Boston, Bowden unsurprisingly said "wait and see," rather than being a solid buyer or seller.

"Trade deadline position: Wait and see," Bowden wrote. "The Sox have the pitching to stay in the race but have an awkward roster on the position player side with strong needs for an impact middle-of-the-order bat and an upgrade at third base. If they can keep themselves close to a playoff berth, they could be buyers and they have the prospect talent to make some deals. However, they also could sell or balance the approach by trading a major-league outfielder for a major-league infielder of equal value."

Boston has the pieces needed to go out and swing a blockbuster deal to bring a big bat to town. That's what the team needs. The farm system is good, the Red Sox have an outfield surplus to work from and there are plenty of arms at Boston's disposal. On the other hand, if the Red Sox don't turn things around, they could easily bring good pieces back by trading someone like Duran or Gray.