Accomplishments: 3x All-Star, NBA Champion (2006)
Team(s): Celtics, Mavericks, Hawks, Timberwolves
Currently: Wishing Range Rovers and gambling debts appreciated like IRA's and bonds 

Antoine Walker recently started an athlete management company. While doctors hang medical degrees and champions wear rings, Walker has the dubious honor of blowing $110M in career earnings to bolster credibility. Sadly, he'll probably add half of next year's lottery picks to his list of clients. 

Besides bouncing checks and filing for bankruptcy, Walker was cut by the D-League's Idaho Stampede. According to Sports Illustrated, he was without a car, surviving on cold cuts and fast food, and playing in front of crowds as small as 155 when he was shown the door. And you thought you were having a bad day.