12. Luis Castillo

Year: 2007
Contract: $25 million/Four years
Team: New York Mets
Signing an injury prone 32-year-old to a long term contract is just the kind of fuckery the New York Mets became known for in the late 2000s. Sadly (for Mets fans at least), it's also the kind of nonsense they perpetrated in the early 2000s, mid '90s, early '90s, early '80s, mid and late '70s...you get the picture.