10 Worst MLB Contracts For the 2023 Season

Ryan Phillips
Los Angeles Angels v Oakland Athletics
Los Angeles Angels v Oakland Athletics / Lachlan Cunningham/GettyImages
2 of 11
Chris Sale
Boston Red Sox Spring Training / Maddie Malhotra/Boston Red Sox/GettyImages

10. Chris Sale, Boston Red Sox

In March of 2019, the Red Sox signed Sale to a five-year, $145 million contract that was definitely a "thanks for helping us win the World Series" deal. The pact has been an abject disaster. In 2019, after agreeing to the deal, Sale went 6-11 with a 4.40 ERA. And that was his best year. Since signing, Sale has made 36 starts over four seasons while missing the 2020 campaign entirely. The 33-year-old has been a walking injury for years.

Sale is still due $55 million through the 2024 season -- $27.5 million per year. He also has a vesting option for 2025 valued at $20 million. So the Red Sox may end up owing him $75 million over the next three years.