
2) Greg Swindell-4 years, $17 million
The Astros signing of Greg Swindell couldn't have gone worse. Through the first seven years of his career, Swindell had a 3.60 career ERA. During his four years in Houston, his ERA swelled to a 4.48. Swindell signed with great expectations and failed to meet all of them.
Swindell was a negative bWAR player during his time in Houston, but was good for over 30-bWAR in the other 13 years in his career. He just couldn't handle the pressure of the deal. Houston moved on in year four of the deal, with Swindell carrying a 7.83 ERA through eight games, including a demotion to the bullpen.
Were it not for one worse signing, this would be the worst signing in franchise history.