28. Zack Britton, 2019: Three Years, $39 Million
Prior to the 2019 season, the Yankees "shocked" onlookers by shelling out to keep Zack Britton, after acquiring the left-hander as a supposed rental during the summer of 2018.
He didn't make it to the end of the deal healthy, succumbing to elbow issues midway through the 2021 season (his contract, via triggered opt-ins, was eventually extended through 2022).
Britton will go down as a very fine Yankee who battled hard to get back to his position at the tail end of an injury-wrecked season last year. We'd rather have his 2019-20 seasons than Dillon Tate, whom the Yankees traded to Baltimore in exchange for his services.