Year: 2000
Contract: 7 years, $86 million

After three seasons on Portland's talented, yet underachieving teams of the late '90's, Brian Grant went looking for greener pastures. Specifically, Miami. The Heat offered Grant the max and he sure as hell wasn't going to turn it down. Unfortunately, things didn't pan out for Brian in Miami. His numbers remained steady, yet nowhere near worthy of his salary. Fortunately, the Heat found a willing taker for his contract: The Los Angeles Lakers and Shaquille O'Neal. Dumb luck or another Machiavellian move by Pat Riley? You decide.