3. Hassan Whiteside, Miami Heat
The contract: 4 years, $98 million (2016)
From being a diamond in the rough to a $100 million man, the Hassan Whiteside story is quite unique. However, it came to a crashing end after he signed a nearly $100 million contract extension with the Miami Heat. During the summer of 2016, Whiteside was a free agent and was entertaining the open market. In the end, the Miami Heat rolled the dice on the big man (that they developed) and gave him the max contract he was seeking.
Looking at his raw numbers, you would say that he was quite productive even after signing his big deal. But when you watched the Heat closely, it became quite apparent that he was a bigger issue than what the stat sheet would suggest. Whiteside fizzled out for the Heat to the point where he was benched close to the end of his tenure in Miami.
What made this contract worse was the fact that this was the same offseason in which the Heat let Dwyane Wade leave for Chicago because they didn’t want to pay him. The Heat had difficulty in moving Whiteside’s contract and could not do it until he became an expiring deal. Even then, the return was not great for the Heat.
If the Heat had to do it again, you’d have to assume the Heat probably decided to give that $100 million to Wade instead.