1. Jacoby Ellsbury
When you get rubbed out by the mafia years before your contract is supposed to expire, only to resurface years later as part of a Red Sox troll, you know the deal probably went south at some point.
Hey, at least we knew where Pavano was … well, after 2006, at least. And at least Pavano wasn’t signed for seven years!
Boston’s ultimate revenge on the Bombers came when New York chose to sign Jacoby Ellsbury to a seven-year, $153 million contract after the 2013 season. They watched the insufferable “Get Beard” team win a third Red Sox ring in less than a decade and decided any price would be worth it to steal that team’s heart and soul, Johnny Damon-style.
They were incorrect.
People forget Ellsbury’s 2014 season was actually good. People forget that because 2014 was a completely forgettable season in Yankees history, and the Ellsbury expectations were much higher at the time (probably wrongfully so, but still) than 16 homers, 70 RBI and a 111 OPS+.
After that, though, things went off the rails. Ellsbury played in 111, 148, and 112 games in the next three seasons, posting OPS+ marks under 100 and typically looking more like a replacement player than an electric superstar. The short porch at Yankee Stadium didn’t help him at all; the power was gone (seven, nine, and seven home runs). Nobody was expecting a replica of 2011 (32 bombs!), but the low-20s at our tiny ballpark would’ve been nice.
Entering 2018, the Yankees clearly had no intention of using him if they didn’t have to, and he missed the entirety of the next two seasons with a hip labrum tear, plantar fasciitis, and a shoulder issue. At least, that’s what we were told.
When the Yankees released him, they tried to sneak out of the remainder of his contract by claiming he’d received unauthorized medical care, an objectively scummy move. The MLBPA agreed, filing a grievance and getting Ellsbury paid (and nearly costing the Yankees a draft pick in the process).
Ellsbury was technically passable on the field for the Bombers, but when his deal went south, the Yankees couldn’t take the embarrassment, and the ugliness of this deal — most of which falls on Yankee management — makes it a clear No. 1.