15. C.J. Wilson: Five Years, $75.5 million, 2011
C.J. Wilson was not the big fish the Angels managed to reel in during the 2011 offseason, but he was coming off of a season which saw him make his first all-star team and finish sixth in the AL Cy Young balloting for the Rangers.
The Angels signed Wilson who joined Jerad Weaver, Ervin Santana, and Dan Haren in what was supposed to be a dominant rotation.
The southpaw wasn't bad by any means as an Angel, but wasn't quite the dominant pitcher he was developing into as a Ranger.
Wilson only pitched in four of his five years and in those years he posted a 3.87 ERA in 119 starts. In his one playoff start he was dreadful, allowing three runs while recording just two outs.
That start, combined with his slightly underwhelming performance, and the fact that he was hurt for an entire season of his big deal are reasons why he's on this list. The contract wasn't a complete disaster like the others, but it wasn't great either.