1) Jim Clancy-3 years, $3.4 million
The Astros signed Jim Clancy in 1988 with hopes that he would become Nolan Ryan 2.0. Seeing as he carried a 4.10 ERA for his career after 12 seasons in Toronto, these wildly unfair expectations were obviously never going to be met, but nevertheless, Clancy signed with plenty of hype.
He answered the hype with a 9-25 record in three seasons, posting a 5.02 ERA and a 1.48 WHIP.
Clancy was sent to the minor leagues in 1991 before being traded to Atlanta.
Clancy would have been a bad signing had Houston hoped he be a back of the order innings eater. That they hoped and expected him to be a dominant workhorse when he has 12 prior years showing precisely who he was makes the decision even more confusing.