4. Dennis Rodman (-$1,000,000)
Former NBA player, Dennis Rodman was drafted in 1986 by the Detroit Pistons and he continued to play professional basketball for 20 years for several teams, including the San Antonio Spurs, Chicago Bulls, Los Angeles Lakers and Dallas Mavericks. However, Rodman is as well known for his antics and controversies, as he is for playing basketball. He famously wore a wedding dress to promote one of his books, he’s made several trips to North Korea to party with dictator Kim Jong-Un, and he’s had a slew of legal troubles resulting from his addiction to alcohol. Although Rodman is said to have made over $30 million from his basketball contracts, the Hall of Famer has nothing to show for it. Bad investments, bad choices and $800,000 in back child support have left Dennis with a net worth of negative $1 million.