At 36 years old, Boston Red Sox starter Sonny Gray had a career renaissance in 2026, posting a 2.72 ERA in 29 starts, the fifth-lowest among all qualified American League starters and eighth-lowest among all qualified starters in the sport. On Friday, Gray's mutual option was declined, and the 14-year veteran is set to hit the open market on Monday when free agency officially opens.

Despite the rocky ending to his tenure in Boston, Gray said he was open to returning to the Red Sox in 2027. However, with starters Johan Oviedo, Kutter Crawford and Tanner Houck returning from injury at the end of the season, and figuring to push for a spot in the rotation in 2027, it seems unlikely the Red Sox will be willing to meet the market to retain Gray. 

If the 36-year-old doesn't return to Boston, these three teams are possible destinations. 

One factor that Gray has been very vocal about in his previous trip to free agency was that he wants to be close to home in Nashville. Throughout the regular season, Gray would take day trips on off days to be with his family. Enter the Braves. Atlanta is the closest city with a major league team to Nashville; the Braves also have a need for a consistent veteran starter. 

The Braves rotation is of course anchored by former Red Sox starter and 2024 National League Cy Young Award winner Chris Sale. The 37-year-old put together another incredible season in Atlanta in 2026, posting a 2.16 ERA in 27 starts that should see him finish top three in Cy Young Award voting. However, beyond Sale, there are plenty of question marks in the Atlanta rotation. Youngsters A.J. Smith-Shawver and Spencer Schwellenbach have both shown promise at the major league level, but have struggled to stay healthy. Rookie Didier Fuentes served as a crucial bullpen piece in 2026 and could move to the rotation in 2027. But as Red Sox fans know all too well, relying on prospects to play major roles immediately is asking for trouble. 

Gray would provide Atlanta with a dependable veteran starter behind Sale. 

Perhaps the biggest surprise team of 2026, the White Sox are way ahead of schedule, making the playoffs for the first time since 2021 and winning a postseason series for the first time since 2005. Ultimately, Chicago's undoing was their lack of rotation depth. After relying on Sean Burke, Davis Martin, Erik Feede, and others, White Sox general manager Chris Getz swung a trade deadline deal with the Seattle Mariners to land veteran starter Luis Castillo. However, Castillo was moved to a bullpen role after struggling as a starter. Ultimately, the White Sox finished the regular season with a rotation ERA of 4.60, the fifth-worst in baseball. 

The White Sox do have two of the best pitching prospects in the sport, left-handers Hagen Smith and Noah Schultz, both of whom played a major role coming out of the bullpen in the playoffs. However, they lack the veteran at the top of their rotation to both serve as a stopper and show those young arms the ropes in the big leagues. 

Finally, a trip up the CTA's red line to the North Side of Chicago, where the Cubs have a massive need for starting pitching after four of their five starters, Matthew Boyd, Kevin Gausman, Clay Holmes and Shota Imanaga, are set to hit the free agent market. 

The Cubs do have Justin Steele returning from Tommy John surgery that kept him out for the entirety of the 2026 season. However, it's unclear exactly what he'll give after making only three starts since the start of 2025. 

As the Cubs look to rebuild a rotation that finished 18th in rotation ERA in the regular season, Gray seems like a near-perfect fit. 

If the Red Sox and Gray are unable to come to an agreement on a deal before Monday at 5:00 p.m. ET, he is free to sign with other teams.