Career: 1990-2004
'90s team(s): New Jersey Nets (1990-95), Philadelphia 76ers (1995-99), Charlotte Hornets (1999)

He was the Detroit Public School's Athletic Commissioner but no longer holds that position. Depending on who you believe, he owes anywhere from $2.2m to $4.7m to over 50 creditors (one of whom is NBA Hall of Famer and current Mayor of Detroit, Dave Bing). When you're facing two $1+ million dollar lawsuits and bankruptcy that means you've hit rock bottom. But in Detroit it just means you fit in.