In 2014, Ellsbury became a free agent. The Yankees shocked the baseball world by signing him to a seven year $153 Million Dollar contract. This is an average of almost $22 million a year. In his first 7 seasons he was paid a total of $21 million. Now the Yankees agreed to pay him more than that total EVERY YEAR for 7 years.
In the end , Ellsbury only played 4 of the 7 years. His best seasons with the Yankees were equivalent to his worst years with the Red Sox.
It is clear that Jacoby Ellsbury will not play professional baseball again. He has a legal fight with the Yankees, about the $26 million still owed to him. Even without that money the Yankees have paid Ellsbury over $126 million dollars. For that investment they had an outfielder who never hit over .271 in a year. He hit 39 home runs in 4 years. He was known for stolen bases. Yet he stole 102 bases over 4 years for an average of 25 a year. It seems like they got average production for 4 years followed by no production at all for the last three years of the contract.