Sonny Gray’s strong first season with the Boston Red Sox has put him in position to test free agency, with the Chicago Cubs already viewed as a potential landing spot for the veteran right-hander.
Gray put to rest speculation about retirement after the Red Sox fell to the New York Yankees in the American League Wild Card Series. He has made clear he intends to keep pitching in 2027 while remaining open to a return to Boston or a move elsewhere.
“My family and I have talked about it and it’s an easy decision,” Gray said. “I still want to win a World Series, whether that is [with] Boston or with whoever wants me.”
The 36-year-old went 18-5 with a 2.72 ERA and a 1.15 WHIP in 29 starts and 169 innings this season. Those marks represented career bests in both wins and earned run average for the three-time All-Star, who also struck out 149 batters.
Gray arrived in Boston via a November trade from the St. Louis Cardinals. At the time of the deal, he had one year remaining on his contract along with a mutual option for the 2027 season.
That option is valued at $30 million and carries a $10 million buyout. Mutual options are rarely exercised by both sides, and the expectation is that Gray will decline his portion and reach the open market.
Doing so would allow the Red Sox to negotiate a new deal if they choose, but it would also free Gray to field offers from any club. The organization has not publicly detailed its plans for the option or a potential re-signing.
Early free-agent projections have already connected Gray to the Cubs. Sports Illustrated’s Justin Binkowski listed Chicago among the top possible destinations, citing the club’s rotation needs and Gray’s prior experience in the National League Central.
“If Gray does become a free agent, he could be one of the top candidates to be Chicago’s ace next season,” Binkowski wrote. “Gray has experience pitching in the National League Central with the Cincinnati Reds and the St. Louis Cardinals. A return to that division could be an option for the veteran hurler if the Cubs revamp their rotation.”
The Cubs have been consistent postseason contenders and appear likely to pursue starting pitching help this winter. Gray’s familiarity with the division from his time with the Reds and Cardinals adds to the fit from Chicago’s perspective.
For the Red Sox, Gray’s performance provided a significant boost to a rotation that also included Garrett Crochet, Ranger Suarez and others. He led the major leagues in wins and ranked among the league leaders in ERA while logging a full workload.
Losing that production would force Boston to address its starting depth through free agency or internal options. The team finished the regular season at 87-75 before the early playoff exit.
Market estimates from Spotrac project Gray’s value at roughly two years and $63.5 million. That average annual figure exceeds the $30 million option, which could influence whether he pursues a multi-year deal elsewhere.
Gray will turn 37 in November, and his improved results in Boston compared with his final year in St. Louis have left some evaluators questioning how much of the gains were tied to the Red Sox environment. Any new contract will also unfold against the backdrop of upcoming collective bargaining agreement talks, which could affect the broader free-agent landscape.
From Boston’s standpoint, retaining Gray would keep a proven innings-eater and postseason-experienced arm in the fold. The club will weigh that possibility against other free-agent targets as it works to strengthen its roster for another run at the postseason.
