10. Bobby Bonilla

Year: 1992
Contract: $29 million/Five years
Team: New York Mets
In 1992, Bobby Bonilla had just finished a season in which he made his fourth consecutive All-Star team and his third Silver Slugger award. But in his first season after signing with Mets, Bonilla's batting average dropped more than 50 points. Besides 1994, his numbers never really lived up to the potential he showed while in Pittsburgh. He was traded to the Orioles in 1995 but that wasn't the end of Bonilla's tumultuous relationship with the Mets. In 2000 it was revealed that "The Mets agreed to pay out the remainder of Bonilla's contract by deferring the $5.9 million that he was due. The Mets will pay him 25 equal payments of $1,193,248.20 every July 1 from 2011 until 2035, assuming an annual interest rate of 8% during the period 2011-2035." If Bonilla was an ex-girlfriend of the Mets, that contract was the illegitimate baby that requires beastly child support payments. Not that we've experienced that kinda thing...