Entering the offseason, the Boston Red Sox had three immediate orders of business: Make decisions on Sonny Gray's mutual option, Garrett Whitlock's team option and clear four spots from the 40-man roster to make room for players returning from the 60-day injured list. The team got right to clearing roster spots, trading outfielder Nate Eaton to the Athletics and infielder Tsung-Che Cheng to the Detroit Tigers on Thursday. Then on Friday, Gray’s mutual option was declined, awarding him a $10 million buyout and sending him to free agency.  What was seemingly the easiest decision of the bunch, picking up Whitlock’s $8.25 million team option, was dragging out, leading to speculation that a longer-term extension might be in the works. 

That wait ended on Sunday, though, as Andrew Parker of SoxProspects.com is reporting that the team will be exercising Whitlock’s option to keep him in Boston for 2027. 

After starting his career in the New York Yankees organization, Whitlock was selected by the Red Sox in the 2020 Rule 5 Draft. Whitlock made 54 regular-season appearances in 2026, setting things up for All-Star closer Aroldis 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.

After unsuccessfully experimenting as a starter in 2022 and 2023 and an injury-shortened 2024, Whitlock has established himself as one of the best relievers in baseball over the past two seasons. In 116 appearances, Whitlock has posted a 2.03 ERA, the ninth-lowest among relievers, with a 2.15 FIP (fielding independent pitching), the sixth-lowest mark in that stretch. Among 143 qualified relievers, Whitlock ranks seventh in win probability added (5.77). 

Whitlock signed a four-year, $18.75-million extension with the Red Sox ahead of the 2023 season, with club options for 2027 and 2028 worth $8.25 million and $10.5 million, respectively.  

After trading Eaton and Cheng on Thursday, the Red Sox got started on clearing space on their 40-man roster for the seven injured players returning from the injured list. However, the team still needs to clear two spots on the roster before Monday, when the injured players return. 

Beginning at 5:00 p.m. ET on Monday, free agency will officially open, allowing free agents to negotiate and sign with other teams. Patrick Sandoval, Isiah Kiner-Falefa, and Gray are the only members of the 2026 Red Sox who will hit the open market.