Rashard Lewis: 6 years, $118 million (2007)
Rashard Lewis was one of the original “stretch 4’s” in the NBA, before it became the thing that teams look for. Drafted right out of high school, Lewis had a nice nine-year career with the Seattle Supersonics. But after becoming a free agent at 29-years old, the Orlando Magic signed Lewis to a six year deal worth $118 million.
Why they thought it’d be a good idea to pay that much to someone entering their 30’s is anyone’s guess. To make matters worse, two years into his deal, Lewis was suspended for testing positive for a banned substance, which led to allegations that the prime of his career came as a result of performance-enhancing drugs.