Andray Blatche: 5 years, $35 million (2007)
It was dubious enough that the Washington Wizards handed a five-year, $15 million contract forward Andray Blatche, given that he averaged 3.2 points and 2.7 rebounds in 85 career games (spanning three seasons). But then, General Manager Ernie Grunfeld doubled-down on the bad deal, adding $28 million to Blatche’s deal, effectively making it a 5-year, $35 million deal.
There was absolutely no reason for Grunfeld to hand Blatche that type of money, considering the player was well-known for severe immaturity issues and a horrible work ethic. Unsurprisingly, Blatche was maddeningly inconsistent after signing said deal, but blamed everyone except himself for his shortcomings. Just two seasons later, Washington traded him away to the Brooklyn Nets.