The Orlando Magic Sign Rashard Lewis (2007)

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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.