This offseason brings big decisions to the Red Sox front office. From a reliable arm in Sonny Gray to a homegrown star in Jarren Duran, the Red Sox must face their toughest challenge yet. They scooted by last offseason; now they face a pair of decisions that could have both short-term and long-term effects on the organization.
Sonny Gray Has Exceeded Boston’s Expectations
Sonny Gray, 36, was acquired via trade with the St. Louis Cardinals last offseason. Upon being acquired, Red Sox fans had high hopes for what he could bring to the team – and he did not disappoint. He had a standout debut season with the Red Sox in 2026, finishing the season with a record of 18-5 and a staggering Earned Run Average (ERA) of 2.72 in a whopping 169 innings. Some argue he was snubbed for an All-Star appearance; at that point in the season, he held a 10-1 record (tied for the second-most wins in MLB).
In Gray’s 14th MLB season, he made himself a Cy Young contender for Boston. Now, one question looms overhead: what will the Red Sox do with him?
Sonny Gray’s Future
As mentioned, this past season was Gray’s 14th season in the majors. Following the disappointing end to the Red Sox’s season, there was speculation that he could retire. Since then, though, Gray has personally denied those rumors. According to the Boston Globe, Gray wrote, “My family and I have talked about it and it’s an easy decision… I still want to win a World Series, whether that is [with] Boston or with whoever wants me.” So, where will Gray be pitching next season?
Sonny Gray has expressed interest in staying with the Red Sox, but his time in Fenway hasn’t been without tension. As the game’s two-game starter in Boston’s disastrous playoff series vs. the Yankees, manager Chad Tracy pulled him in the fifth inning after he allowed two runs on just 70 pitches. Following the 9-2 loss, Gray spoke about being taken out of the game, saying, “I think I’m the best pitcher in the American League going through the order a third time. I think that’s a fact… I would have liked to have been trusted in that moment.”
The Price to Pay Gray
If the Red Sox front office does decide to stick with Gray, it won’t be cheap. As a free agent, he is projected to come in with a price tag of $60 million or more on a multi-year deal. Keeping Gray would significantly benefit the Red Sox starting rotation, given his potential and reliability. But the Red Sox have a history of dealing high-earning players; will that trend continue? This decision could alter the 2027 season, for better or for worse.
Jarren Duran – Built in Boston
Another tough decision the front office faces this offseason is whether to keep Jarren Duran. Boston drafted Duran in 2018, so there is no doubt he’s been loyal to the organization. He became a household name in 2024 with a breakout season, when he was named an All-Star. In the All-Star Game, he hit a home run that became the game-winner and helped him earn Most Valuable Player.
This was no easy feat, but 2024 was his year. He played 160 games for the Red Sox and finished the season with a .285 batting average and 191 hits. Beyond his bat, he stole an impressive 34 bases, tying for 9th in all of the majors. Following his incredible 2024 season with the Red Sox, he continued to produce above-average stats in 2025. Although he wasn’t an All-Star, he hit .256 with 159 hits in 157 games.
Jarren Duran’s Future
After two tremendous seasons, Duran’s numbers began to decline. In 2026, he posted a worrisome .207 batting average with just 114 hits in 151 games. He was also prone to strikeouts and stole only 21 bases, though he hit 20 home runs (his season high is 21 home runs – 2024). Even with a 20-20 season, fans want to see him shipped out of Boston. Not only because of his poor performance in the 2026 regular season and short postseason, where he went 0-for-3, but also because of the paycheck he will likely be looking for. According to Spotrac, Duran is projected to earn over $10.5 million in 2027.
Yet again, the Red Sox must decide on keeping or trading a player based on their paycheck. Reports suggest the Red Sox will trade Duran this offseason, clearing the traffic jam in the Fenway outfield. This would make room for the team’s young talent, such as Roman Anthony, to officially take over left field.
Trading Duran now, at his career low, may not be worthwhile. Boston would be unlikely to get a big name in return, so they would have to hope for at least a young prospect. Duran could also make a comeback year, returning to the player he was in 2024. It’s really a coin toss.
Offseason Uncertainty
Ultimately, the Red Sox front office has big decisions to make. This offseason is shaping up to be both intriguing and unpredictable. The Red Sox have many options, ranging from keeping both Gray and Duran to letting them both go. Will Boston continue the trend of moving on from high-payroll players, or will they take chances this time? These decisions will undoubtedly have major implications for the Red Sox’ future.
