Detroit Tigers 6th Worst Contract – Gary Sheffield
We understand if this one feels a bit surprising. The Tigers traded for Gary Sheffield in late 2006, and he went out and had a very solid 2007, batting .265 with 25 home runs, 22 steals, and more walks than strikeouts. It was good for an OPS+ of 119 and 3 WAR. But that wasn’t technically a part of the deal he signed with the Tigers, it was the final season of his three-year deal with the Yankees. Detroit agreed to give him a two-year extension in order to complete the trade, and it was those two years that ended very poorly. This was the first in what proved to be a string of disastrous extensions offered to veterans under owner Mike Ilitch and GM Dave Dombrowski.
Sheffield dealt with some nagging injuries in 2008, complained about playing time, and eventually posted his worst numbers since 1991, hitting just .225 with 19 home runs in 114 games. Sheff was still expected to serve as the team’s primary DH in 2009, but in a shocking move at the end to spring training, the Tigers decided to release him and eat the remaining $14 million on his deal. They did this despite Sheffield sitting on 499 career home runs at the time.