Brian Cashman has hit the jackpot during his tenure as New York Yankees General Manager when it comes to signing free agents. He also has had some misfires that have not worked out. From pitchers to position players, there have been some signings that he would like a do-over with.
Below are five free agents signings that just never worked out for Cashman and the Yankees since 1998.
5. Kevin Youkilis
What a one-year, $12 million disaster. Signed in December of 2012, Kevin Youkilis inking a short-term deal didn’t seem that bad at the time.