9. Jacoby Ellsbury: Seven Years, $153 Million
What is there to say about this? Do we have to say anything about this? What is there to say about Jacoby Ellsbury that has yet to be said?
He was solid for the 2014 Yankees after defecting from Boston and pulling a proto-Damon, but he was borderline unplayable (and rarely healthy) offensively from 2015-17, then was eventually sent into the void, as the Yanks worked tirelessly to prove he never existed in the first place.
Sadly, this figment of imagination took them to court when they took him to task over consulting an outside doctor, only to reemerge when it was time to honor Dustin Pedroia at Fenway. Insipid 'til the end.