Year: 1997
Contract: 7 years, $107 million

Also known as when The Reignman met The Lockout. Shawn Kemp wanted an extension. Management gave one to his teammate instead. Kemp threatened not to play the following season and forced his way into a trade to....Cleveland? Though things started well, when Kemp returned to the team after the lockout, he was barely recognizable. Massively overweight and unmotivated, his career went into a tailspin and he was never the same player again. Would this have happened in Seattle? Who knows. But Cleveland still had to foot the bill.