We’ve seen a number of bad contracts on the Yankees’ payroll over the years, with Jacoby Ellsbury’s deal still making us twitch after six years. But fans might overlook the fact that New York has some current (and still active) risky deals, despite the team performing admirably over the last three seasons and adding Gerrit Cole a few months back.
General manager Brian Cashman has used the organization’s deep pockets over the years, but he’s been forced to scale back as of late (with the exception of Cole and one other player on this list), leaving a lot of his work to be done on the trade market.