The 7 biggest contracts and extensions in Boston Red Sox history
2. Manny Ramirez – 8 years, $160M
Manny Ramirez held the top spot on this list for 15 years before Price came along; the Sox gave him the franchise record-setting contract way back in the year 2000.
No one can argue he wasn’t worth the dough. Over 1,083 regular-season games, he hit a next-level .312/.411/.588 with 274 home runs. He won a Silver Slugger in each of his first six Sox seasons, was an All-Star every year he was here, and led the team to two World Series championships and an assortment of less-successful postseason runs. In 2004, he was their World Series MVP. If not for the performance-enhancing substance issues, he’d be in the Hall of Fame with several of his former teammates. He’s with them in the Red Sox HOF, though.
Ramirez also ended up in Los Angeles; the Sox traded him to the Dodgers in 2008. But like a less protracted Bobby Bonilla, Manny’s contract included many years of deferred salary; the Sox will be paying him until 2027.
3. Adrian González – 7 years, $154M
The Dodgers are a veritable dumping ground for Boston’s biggest contracts, because Adrian Gonzalez ended up there, too, and he’s not the last player on this list for whom that’s the case.
Boston acquired González from the San Diego Padres in December 2010 and by April 2011, he had a massive contract extension. He led MLB with a career-high 213 hits, though it was his first season without 30 or more home runs since 2006. He was an All-Star for the fourth year in a row, won his third Gold Glove in four years, his first Silver Slugger award, and finished seventh in AL MVP voting.
The following summer, he was part of the great salary dump of 2012. The Sox sent him, Josh Beckett, Nick Punto, Carl Crawford, and $11M to Los Angeles for James Loney, Iván DeJesús Jr., Allen Webster, Jerry Sands, and Rubby De La Rosa.
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.’
6. Trevor Story – 6 years, $140M
Trevor Story’s first season in Boston was more of a whimper than a bang. Over 94 games – his lowest total in any 162-game season of his career – he hit .238/.303/.434 with 22 doubles, 16 home runs, and 122 strikeouts. He’s always struck out at a high rate, but this season, his SO% increased by 7.4%, and his walk rate dropped by 0.8%. It was also the first time in his seven big-league seasons that he collected fewer hits than games played.
It wouldn’t be fair to pass judgment on this contract after one injury-riddled season. He has five more guaranteed years to prove himself.
That said, it was a somewhat questionable signing from the start, considering he was coming off the worst season of his career, dealing with elbow issues, and the money could’ve simply gone to Xander Bogaerts.
Through no fault of his own, Story’s contract will be judged in the context of whatever happens with Bogaerts. If Bogaerts doesn’t re-sign with the Sox, Story will likely move to shortstop, though it’s unclear if his arm can handle the position anymore. And if Bogaerts plays better with his new team than Story does in Boston, it will have been a mistake to pay him when they could’ve simply given Bogaerts a raise, which would’ve been the less-expensive move.
7. Xander Bogaerts, 6-year extension, $120M
Bogaerts’ extension makes the top ten, but make no mistake: the Red Sox were underpaying him.
When Bogaerts approached the Sox about an extension in the spring of 2019, he made it clear that he wanted to stay in Boston and proved it by taking a team-friendly deal. He then immediately established that he was underpaid, by having the best season of his career, hitting .309/.384/.555 with 52 doubles and 33 home runs over 155 games.
Bogaerts opted out following the 2022 season, but of the players on this list, he’s one of the only ones who actually lived up to the contract he received.
The Sox should give him another one.
