It’s hard to put into words just how big of a disaster Jacoby Ellsbury’s tenure was with the Yankees. From the beginning to the end he was an awful fit in pinstripes and struggled to stay healthy. There’s no doubt he’s the worst free-agent signing the team has ever made and he’s definitely up there amongst the worst in major league history.
When the Yanks signed him to his mega-deal on December 3rd of 2013 I’m sure a lot of fans were surprised to see him join the team after spending the first seven years of his career with the Boston Red Sox.