The 20 worst free agent signings in NBA history

Derrick Rose, Chicago Bulls NBA (Photo by Maddie Meyer/Getty Images)
Derrick Rose, Chicago Bulls NBA (Photo by Maddie Meyer/Getty Images) /
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#2. Grant Hill: 7 years, $93 million

The NBA career of Grant Hill has three distinct chapters. The first was his incredible six-season run with the Detroit Pistons, while the second was his disastrous seven-season stretch with the Orlando Magic. Hill was initially meant to form a big three in Orlando with Tracy McGrady and Tim Duncan. However, the Magic blew it with Duncan like they did with Shaq, and Hill couldn’t stay healthy.

After being fairly durable through his first six seasons, Hill missed a staggering number of games in his first four years with the Magic. In fact, he missed 187 games during that span before finally having a relatively healthy 2004–05 season, in which he made the All-Star team for the sixth and final time. That was short-lived, however. He played just 29 games the following year and only 65 in the final year of his seven-year deal, respectively.

Had Hill stayed healthy, he likely would have lived up to the contract. But instead, he missed the equivalent of three full seasons, making it among the worst ever signed. While things didn’t work out for Hill in Orlando, he would play four mostly healthy seasons in Phoenix before retiring with the Clippers. It’s really too bad Hill ended up on this list, given how great he was to start his career.