Career: 1989-2003
'90s Team(s): San Antonio Spurs (1990-99)

"The Admiral" co-founded the Admiral Capital Group which invests in real estate and the hospitality industry (in Robinson's case that means nine different hotels). David's business savvy drew praise from Wall Street legend and complete and utter economy wrecking shithead Jamie Dimon (he's a big name though). On a personal note, despite making over $110 million in his career, Robinson has told his kids he'll pay for their college (though one son is headed to Notre Dame to play football) and then they'll get no inheritance. That's called tough love. We wouldn't expect anything less.