Year: 1996
Contract: 7 years, $101 million

You could say Juwan was the one who started it all. An impressive rookie and sophomore campaign led to an $89 million offer from the Bullets. Enter eternal shit stirrer Pat Riley and a $101 million offer. Howard, no dummy, quickly accepted the deal only for the league to rescind it due to a miscalculation by Miami. They didn't have the cap room to make that offer. After a lengthy legal battle, Howard ended up back in Washington with $101 milli as the first NBA player to ever sign a $100+ million contract. After one appearance in his first two seasons, he was never an All-Star again. There's some trivia for ya.