15. New York Yankees
Jacoby Ellsbury, 7 years, $153 million, 2014-20. Boras Corp.
The Yankees signed Jacoby Ellsbury prior to the 2014 season. At the time their lineup lacked punch, featuring only one player (Robinson Cano) who had hit more than 17 home runs or batted above .275. Elslbury didn’t provide power, but he was a .298 hitter and fast enough to lead the American League in steals with 52.
More importantly, he had done so in Boston, meaning that New York’s gain deprived the Red Sox of a player who had been a key asset in their 2013 World Series win.
The deal may have made a lot of sense for a season or two. In New York, Ellsbury‘s average has hovered around .265. He generated a 111 OPS+ in 2014, contributing 39 steals and a 3.6 WAR. Since 2015, however, Ellsbury has become a fifth wheel, his presence on the roster rendered more redundant by the successive developments/acquisitions of Aaron Hicks, then Aaron Judge, then Giancarlo Stanton, then Andrew McCutchen.
Hip problems that eventually necessitated surgery sidelined him for all of 2018, and make his status for 2019 questionable. On their winter roster, the Yankees – who activated him from the disabled list in October — list him as their backup center fielder.
On a roster as famously rich as New York’s, it is noteworthy that whether he plays or not, Ellsbury at $21.14 million might enter 2019 as the third highest-paid Yankee, behind only Stanton ($26 million) and Masahiro Tanaka ($22 million). Indeed, it’s not out of the question that he still holds that distinction in 2021.