Dennis Rodman – $500,000

From dating Madonna to breaking his private parts three times and being best buddies with Kim Jong-Un, NBA star Dennis Rodman has led a very colorful life indeed. During his professional career, Rodman was known for his wacky rainbow-colored hair and antics on the court. Although Rodman has been married three times, most recently to Michelle Moyer, it has gone down in flames each time. That is if you are not counting the time he tried to marry himself, dressed in a bridal gown. Although Rodman reportedly earned $27 million in the NBA, his extravagant lifestyle and financial mismanagement mean the former Chicago Bulls player is worth only $500k today.