Dennis Rodman, 60 Years Old

Who can even forget Dennis Rodman? As one of the key players of Chicago Bulls from 1995 to 1998, he has contributed a lot to the team that helped them win several championships. Many would assume that he is living the life with all the money he earned back then, but with his eccentric lifestyle, his investment money is not doing so hot lately. Aside from the fines that he paid back in the days, Rodman was also a known lover of booze. This is one of the reasons why his money has been depleted.

Though he is no longer visible on the basketball court, it appears that he has become a bit of a diplomat to North Korea. He has already made several trips to the country and was well received too. He earned a sponsorship from Pot Coin, which he often wore while he was in the country.