2. Ville Leino – Buffalo Sabres: 6 years, $27 million
This deal, 3 years later, actually manages to look even more outrageous than it was when the signing was originally made. Coming off his first career year in Philly, Leino notched a career high 53 points finding success on a line with Briere and Hartnell. After this solitary good season, the Sabres pulled the trigger on Leino, signing him to a ridiculous $27 million deal. Since the signing, Leino constantly finds himself in the doghouse and has yet to score a goal this season in 38 games. In 106 games as a Buffalo Sabre, Leino has scored 10 goals and collected 41 points in his 3 seasons. The Sabres have already began to shop around Leino’s name but his laughable contract will almost make it impossible to deal him to another team. Look for the Sabres to perhaps buy out this contract at the end of the season or at the very least waive it.