14. Boston Red Sox
The Red Sox are getting ripped for their refusal to spend. This winter they lost free agents Xander Bogaerts and J.D. Martinez, and negotiations with free agent-to-be Rafael Devers are said to be floundering.
A short time ago the team’s inability to agree to terms of an extension with Mookie Betts led them to trading their star right fielder.
Boston’s recent experience with long-term deals may have poisoned the team’s attitude. The team has since 2016 signed three players to headline-grabbing big-dollar contracts, and all three have thus far come up craps.
In fairness to the truth, two of those deals involved pitchers, a notoriously chancy group to commit to long-term. In 2016 the Sox gave a seven-year, $217 million deal to David Price, a franchise record both for dollar amount and AAV ($31 million.)
Price helped the Sox to the 2018 World Series title, but has done little since for either Boston or the Dodgers, to whom he was traded in 2020.
Then prior to the 2020 season they signed Chris Sale for $145 million over five seasons. A star since being obtained from the White Sox in 2016 who was also a major player in the 2018 World Series run, Sale almost immediately broke down.
Since signing the nine-figure contract, Sale is just 5-2 in only 11 starts.
The Sox’ third big deal, consummated last winter, sent $140 million Trevor Story’s way over six seasons through 2027. In 2022, Story delivered only a .238 average with an inglorious 102 OPS+.