Red Sox Reportedly Could Lose Another All-Star to Cubs in Free Agency

There's going to be some heavy interest around the league in the Boston Red Sox star in free agency.

Jun 23, 2026; Denver, Colorado, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches in the first inning against the Colorado Rockies at Coors Field. Mandatory Credit: Isaiah J. Downing-Imagn Images | IMAGN IMAGES via Reuters Connect

Last offseason, the Boston Red Sox lost a multi-time All-Star to the Chicago Cubs in the form of third baseman Alex Bregman. While the offseason is young, it sounds like the Cubs could very well end up having interest in another former Boston star as well.

On Monday, USA Today's Bob Nightengale reported that the Cubs will be "as aggressive as any team" in the pursuit of starting pitching and one name that was mentioned was Sonny Gray.

"The Cubs lost five free-agent starters, and will be as aggressive as any team in baseball trying to completely revamp its rotation. They’ll be in play for Tarik Skubal, and every other marquee free-agent starter from Michael King to Freddy Peralta to Sonny Gray," Nightengale wrote.

Sonny Gray's Market Will Be Interesting

Sep 11, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) pitching during the first inning against the Kansas City Royals at Fenway Park. Mandatory Credit: Natalie Reid-Imagn Images | IMAGN IMAGES via Reuters Connect

It's important to note that since Nightengale shared his column, The Athletic's Sahadev Sharma reported that the Cubs will sit out of the Skubal sweepstakes. We're at a point in the MLB calendar when information and reports surface left and right and information shifts at the drop of a hat. Regardless of the Skubal of it all, Gray actually would make more sense for the Cubs if they're not in the market for the lefty.

Gray had a 2.72 ERA in 29 starts last season and will be a significantly cheaper alternative to Skubal. It would certainly be interesting if in back-to-back offseasons, the Red Sox lost stars to Chicago after going one-and-done in Boston. But it would be a different situation if Gray left, as opposed to Bregman.

Last year, the Red Sox made it publicly known that they wanted to retain the third baseman, but they just didn't get a deal over the finish line. That led to outrage among the Red Sox's fanbase for quite some time. When it comes to Gray, it would be great to have him back. But the perception out there seems to be more in line with him leaving, rather than staying. The Atlanta Braves have been a team connected to Gray in rumors on multiple occasions already this offseason. The Cubs haven't been mentioned as much to this point, until now.

Nightengale reported the buzz on Monday and now it's going to be something to watch. Again, it would be awesome if Boston could find a way to bring Gray back to town. He showed in 2026 that he can still be elite. But there's clearly going to be competition for his services and now the Cubs are a club to keep tabs on.