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.