4. Chris Bosh — 5 Years, $118 Million
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Bosh was an All-Star in two abbreviated seasons (44 and 53 games played, respectively) after signing his max deal in the summer of 2014, but that solid start wasn’t enough to save the rest of the contract.

Recurring bouts with blood clots rendered Bosh unable to play after the 2016 All-Star break, which ended his career with the Heat (and likely the NBA) with three-and-a-half seasons left on his contract. With a condition as serious as Bosh’s, focusing on the value he generated relative to his contract feels crass.

But there’s no denying the deal didn’t work out for the Heat, who eventually agreed with Bosh on a buyout for the remaining final two years and $52 million.

The Heat may have gotten off the hook for some portion of that $118 million, but they had to have been hoping for more than 97 games when agreeing to the deal initially.

All class, Bosh dropped a line to his fans after parting ways with the franchise. He wrote on his personal website: “We went through life together, Miami. You showed me how to stay strong and push through in the toughest moments. And although I didn’t like it at the time, it made all the difference in the long run. It made me a better man, the person I am today. Thank you.”