Starter Sonny Gray and the Boston Red Sox had until Monday, Nov. 2, to decide whether to exercise his $30-million option for the 2027 season. However, the two sides evidently didn’t need that long, as the MLBPA announced that 11 new players entered the free agent pool, including the Red Sox ace, on Friday. The Players’ Association's release doesn’t say which side declined the option. 

Declining the option and hitting free agency was all but a given; the last time both sides accepted a mutual option was 2014. For Gray, the calculus was simple: decline the option, collect your $10 million buyout, and hit the open market where you’ll likely receive a deal in the $25-30 million annually range, and turn what would’ve been $30 million for 2027 into $35-40 million for the season. For the Red Sox, who are already in a precarious financial spot heading into free agency, you decline the option and hope to re-sign the 36-year-old to a multi-year deal with a lower luxury tax hit. 

Gray is coming off what was one of the best seasons of his now 14-year major league career. In 29 starts for Boston, the 36-year-old posted a 2.72 ERA, the fifth-lowest among qualified American League starters and the eighth-lowest among qualified starters in baseball. In addition to posting the second-lowest ERA of his career, Gray finished the season tied for the league lead in wins with 18. Gray anchored the Red Sox rotation in the absence of 2025 American League Cy Young Award runner-up Garrett Crochet, who missed the final five months of the regular season with a left shoulder injury. 

Gray now joins Patrick Sandoval and Isiah Kiner-Falefa as the three members of the 2026 Red Sox to hit the open market. 

Gray’s season ended in frustration as he was lifted in Game 2 of the Wild Card series after just 4.2 innings. The veteran was vocal about being lifted early, saying he would’ve liked to be trusted in that situation. Amid his frustration, Gray was asked whether he’d like to return to Boston, and he simply said, “I don’t know.” 

However, when Gray announced he would not retire and would return to pitch in 2027, he signaled he was open to a return to Boston. Gray and the Red Sox will have until Monday to negotiate a return to Boston before he can negotiate and sign with other teams.  

As the Red Sox look to clear enough roster spots for seven players returning to the 40-man roster from the 60-day injured list on Monday, the team made two trades. First, Boston sent outfielder Nate Eaton to the Athletics in exchange for pitching prospect Jareth Rayo. Then they sent infielder Tsung-Che Cheng to the Detroit Tigers for cash considerations. 

The team still has to clear two rosters spots ahead of Monday.