Should Boston Red Sox Extend Veteran Starting Pitcher?
· Yahoo Sports
The Boston Red Sox were dealt a major blow on April 29 when 2025 Cy Young runner-up Garrett Crochet landed on the injured list with left shoulder inflammation. The 27-year-old ace has yet to return from the injury, yet in his absence the Boston rotation hasn’t missed a beat, posting a 3.56 ERA, the fourth-best mark in baseball over the three-month stretch. There has been no bigger piece of the pitching success for the Red Sox in Crochet’s absence than 36-year-old Sonny Gray, who was acquired in an offseason deal with the St. Louis Cardinals.
Gray is in the final year of the three-year, $75-million deal he signed with St. Louis ahead of the 2024 season. While he does have a mutual option for the 2027 season for $30 million, you’d have to go back to 2014 to find the last time both sides exercised their half of a mutual option. Should Boston decline the pricey option, the team would owe Gray a $10 million buyout.
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Jun 28, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) waves to the crowd during the eighth inning against the New York Yankees at Fenway Park. Paul Rutherford-Imagn ImagesAs the 14-year veteran inches closer to free agency at the end of the 2026 season, should Boston consider offering him an extension to keep him in Boston for the remainder of his career?
Gray has been a revelation for Boston in Crochet’s absence, posting a 2.37 ERA in 14 starts, the second-best mark in the American League in that timeframe and seventh-best across all of baseball. Overall, Gray has a 2.78 ERA in 106.2 innings in 2026, while holding opponents to a .240 batting average.
Is it sustainable?The biggest concern in extending aging starters is how sustainable their success is. In 2025, Lucas Giolito was incredibly effective for the Red Sox, posting a 3.41 ERA in 141 innings. However, an expected ERA of 5.01, a fielding-independent pitching (FIP) of 4.17, and a batting average on balls in play (BABIP) of .273 signaled the veteran right-hander was the benefactor of some good luck and therefore due for regression.
Sep 17, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) pitches against the Athletics during the first inning at Fenway Park. Eric Canha-Imagn ImagesGiolito sat on the open market well into the season before signing a one-year contract with the San Diego Padres, where that regression reared its ugly head as the 32-year-old has posted a 5.16 ERA in seven appearances for the Padres.
Gray has an expected ERA of 3.80, FIP of 3.70, and BABIP of .285, and while that does signal, like Giolito, he may be due for some regression, the numbers are not nearly as stark as the former Boston hurler.
If Gray does sign an extension and regress to his expected numbers, while providing the Red Sox with 160-180 innings, he would still be an incredibly valuable innings-eating starter for the Red Sox, as pitchers like rookies Payton Tolle and Jake Bennett presumably take steps forward to make up for his regression.
Would Gray be interested in an extension?Jun 12, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches against the Texas Rangers during the fourth inning at Fenway Park. Eric Canha-Imagn Images"The veteran, after silencing doubters about his ability to pitch in a big market with a fantastic first four months in a Red Sox uniform, is said to 'definitely' be interested in a contract extension with Boston," wrote MassLive.com's Chris Cotillo and Sean McAdam. Though the pair added that discussions between the two sides had yet to pick up.
What would an extension look like?According to Spotrac, Gray carries an expected value of $18.02 million, meaning a two-year, $36 million deal could ensure the veteran finishes his career in Boston, while saving the Red Sox $10 million from his buyout.
However, Gray would be wise to hesitate in signing an extension, as if the Red Sox reject his mutual option, allowing him to hit the open market, he could still be in line for an $18+ million AAV deal while still netting himself the $10 million buyout. Meaning the Red Sox would likely have to come to an agreement with him to either pay a portion of the buyout or include a higher average annual value to make up for the potential loss in earnings.
Apr 14, 2026; Minneapolis, Minnesota, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch against the Minnesota Twins in the first inning at Target Field. Jesse Johnson-Imagn ImagesRegardless of whether a deal gets done, it likely won't come until after the Aug. 3 trade deadline, as the Boston front office focuses on improving its outlook for the 2026 season.
After allowing five earned runs on 10 hits to the Toronto Blue Jays in one of his worst starts of the season on Saturday, Gray is next slated to take the mound in Thursday's series finale in West Sacramento, taking on the Athletics.
Up next for the SoxBoston will look to bounce back from Tuesday night's 4-3 loss to the Athletics in game three of four from Sutter Health Park in West Sacramento. Patrick Sandoval (0-0, 3.21 ERA) will get the start for the Red Sox opposite Jacob Lopez (5-4, 6.12 ERA) for the A's. First pitch set for 9:40 p.m. ET.
