The 7 biggest contracts and extensions in Boston Red Sox history
4. Chris Sale – $145M
Acquiring Chris Sale from the Chicago White Sox ahead of the 2017 season was the coup of the decade. It required giving up a bundle of prospects, including Yoan Moncada and Michael Kopech, but the Sox got their man. In his first season with the Sox, Sale reached 1,500 career strikeouts faster than any other pitcher in MLB history by innings, and for the first time in his career, reached 300 strikeouts in a season. Despite leading MLB in innings pitched and strikeouts, he finished runner-up to Corey Kluber for AL Cy Young.
Sale was dominant in 2018, too, but missed significant time due to injury. His 2.11 ERA that season remains the best of his career in any year since his brief debut in 2010, but he only threw 158 regular-season innings.
Unfortunately, the Sox made the mistake of giving him an enormous extension after they won the 2018 World Series, either overlooking the concerning injury that sidelined him throughout August and September or hoping it wouldn’t linger. By August 2019, he was done for the year, and in April 2020, he finally underwent the Tommy John surgery the Sox had been hoping to avoid for months.
Since returning from Tommy John surgery in August 2021, he’s only thrown 48 1/3 big-league innings – only 5 2/3 in 2022 – due to a multitude of injuries and ailments, including a rib fracture, a fractured pinky from a line drive, and while he was rehabbing that, he broke his wrist in a bicycling accident. If he can’t stay healthy for the final two years of his contract, the extension could go down as the worst in franchise history due to the combination of excessive spending and missed time, if it hasn’t already.
5. Carl Crawford – 7 years, $142M
Carl Crawford’s time in Boston was an absolute disaster.
After facing him for nine years on the Tampa Bay (Devil) Rays, the Sox got him to jump ship by giving him a seven-year deal worth $142M. He ended up only playing 161 games total between 2011-12, and he hit .260/.292/.419 with 39 doubles, nine triples, and 14 home runs. By comparison, he’d hit .307/.356/.495 with 30 doubles, 13 triples, and 19 home runs in 154 games in his final season in Tampa.
What really killed his chances in Boston was the part he played in their historic 2011 collapse. The Sox had a nine-game lead over the Rays in the Wild-Card race (still in its original format as a direct ticket into the ALDS) at the beginning of September and then went 7-19, dropping down to a tie with the Rays on the final night of the regular season.
While the Rays and Yankees took their last game of the year into extra innings, the Sox took a one-run lead over the Orioles into the ninth inning. Jonathan Papelbon got two quick outs before giving up a single and double to blow the save and tie the game. Then, Robert Andino sent a pitch into left field, where Crawford attempted to make a sliding catch and missed the ball by centimeters. He recovered the ball and threw it home, but the winning run was already in and with Crawford’s former Rays teammate Evan Longoria hitting a walk-off home run against the Yankees in the 12th inning. Boston’s collapse was complete.
Crawford began the 2012 season on the Injured List and after playing for about a month, had Tommy John surgery. Two days later, the Sox traded him to the Dodgers. Since leaving Boston, he’s called the environment ‘toxic.’