Chris Sale

In 2019, the Red Sox handed Sale a huge extension worth $145 million over five years. Considering he’s out recovering from Tommy John surgery for this year and part of 2021, the deal would hurt more for Boston if Sale hadn’t deferred $50 million. He gets $10 million 15 years after it was earned, from 2035-2039.

His contract led to luxury tax concerns that influenced Boston’s trade of David Price and Mookie Betts, but some of that money will be haunting the team financially until Sale is 50 years old. He didn’t pitch in the 2020 season. Sale, and everyone within or rooting for the Red Sox organization, can only hope he returns to form and is the dominant, work horse ace he has been for much of his career.