After Monday’s annual end-of-season press conference, the Boston Red Sox have officially closed the book on the 2026 season and entered the offseason. The Red Sox will have several key decisions to make as they look to retool from a team simply good enough to make the playoffs to one capable of contending for and winning a World Series title. 

With the page officially turned to the 2027 season, these members of the 2026 Red Sox are set to become free agents: 

With 17 arbitration-eligible players and key pieces like Garrett Crochet, Roman Anthony, Ranger Suarez, and Ceddanne Rafaela locked up long term, the Red Sox have only two players from their 2026 roster set to become unrestricted free agents. 

After signing a two-year, $18.5-million deal with Boston ahead of the 2025 season, Sandoval spent much of his time in Boston rehabbing from the 2024 Tommy John surgery he underwent as a member of the Los Angeles Angels. The 29-year-old made his long-awaited Red Sox debut on July 9 against the Chicago White Sox. 

In 15 appearances (13 starts), serving primarily as Boston’s fifth starter, Sandoval posted a record of 1-7 with a 5.12 ERA over 70.1 innings, striking out 9.3 batters per nine innings while walking 4.1 per nine. While his ERA doesn’t jump off the page, a fielding-independent pitching (FIP) of 3.77 suggests he was the victim of some bad luck. 

Ultimately, Sandoval performed well for his role as an innings-eating fifth starter. However, with Tanner Houck and Kutter Crawford back to full health and hoping to push for a spot in the back end of the Boston rotation, it’s hard to imagine the left-hander back with Boston in 2027. 

After spending the 2025 season with the Toronto Blue Jays, the 31-year-old utility man signed a one-year, $6-million deal to join the Red Sox in pursuit of a World Series title. 

Kiner-Falefa performed well in what could be his lone season in Boston, hitting .244/.322/.311/.633 in 66 games, providing plus defense across the infield. He was especially impactful after veteran shortstop Trevor Story landed on the injured list with a sports hernia, hitting .321/.391/.449/.840 in 26 games as Boston’s primary shortstop before landing on the injured list himself with a forearm injury. Upon his return on Sept. 1, Kiner-Falefa struggled at the plate, hitting .143/.265/.167/.432 in 19 games. 

With Nick Sogard and Anthony Seigler emerging as major-league-caliber bench options, Kiner-Falefa will likely be one-and-done in Boston, joining his third team in as many years. 

After Chief Baseball Officer Craig Breslow confirmed reports that All-Star closer Aroldis Chapman passed his end-of-year physical, officially vesting his conditional option for 2027, the Red Sox will have to make decisions on a pair of club options for the 2027 season. 

After being acquired in an offseason deal with the St. Louis Cardinals, the 36-year-old was inarguably Boston’s best starter in the absence of Crochet. In 29 starts, Gray posted a 2.72 ERA, the fifth-lowest mark in the American League and eighth-lowest in baseball.

However, his season ended in discontent as he was lifted from his Game 2 start in the Wild Card round after only 4.2 innings. The 14-year veteran sounded off on the decision in his postgame presser, citing his success when facing batters for the third time. 

Both Gray and the Red Sox have a decision to make on a mutual option for the 2027 season that could keep the veteran in Boston for $30 million. However, you would have to go back to 2014 to find the last time both sides accepted a mutual option. Gray would receive a $10 million buyout if either side were to decline. 

Based on the rocky end to the season, where he answered a simple “I don’t know,” when asked if he would like to return, paired with the idea that he may seek a potential multi-year deal to wrap up his career, it seems likely that Gray will take the decision out of the Red Sox hands, collect his buyout, and hit the open market. 

That said, it’s unlikely the Red Sox would have exercised their side of the pricey option as well, paying the buyout, while potentially looking to sign Gray to a cheaper, multi-year deal to remain with the team. 

However, the 36-year-old had been very vocal in the waning weeks of the season that retirement was very much on the table for him.

The 30-year-old reliever has continued to establish himself as one of baseball's best relievers in 2026. Whitlock made 54 regular-season appearances, setting things up for Chapman, posting a 1.72 ERA, the sixth-lowest mark among 143 qualified relievers. In addition to the impressive ERA, Whitlock ranked 12th among all relievers in win probability added with 2.73.

Boston holds a club option worth $8.25 million to keep the right-hander in a Red Sox uniform for 2027. Breslow was asked on Monday if any decision had been made yet on the option, to which he said no. However, the decision to pick up the option is among the easier decisions the team will make this offseason. 

The Red Sox will have until five days after the World Series concludes to decide on both the options and whether they’ll extend qualifying offers to Sandoval or Kiner-Falefa.