Jacoby Ellsbury's contract isn't a huge disaster yet... but probably will be. I'm not defending the contract, but merely providing a glimmer of hope for Yankee fans to show that not all hope is lost, and Ellsbury's contract isn't a completely lost cause yet.
Like many fans, I often get nauseous thinking of having a 37-year-old Jacoby Ellsbury running around the outfield. If there was an option to go back in time, I'm sure Cashman would go back and not offer him the contract, and we'd all be fine with that. The main concerns with Ellsbury are the fact that long term contracts rarely work out, his injury history, and his poor second half last season.