10. John Daly
There is no denying John Daly is one of the most intriguing characters in the world of golf. His anti-country club appearance and behavior have earned him a legion of fans. It has also cost him a considerable amount of money.
Daly has battled alcoholism for his entire career with at least three stints at the Betty Ford Clinic and recently, was fired by swing coach Butch Harmon, who said, "The most important thing in [Daly's] life is getting drunk." Daly's drinking and antics cause the PGA to suspend him for six months.
But his drinking is not the main source of his economic troubles, however; that comes from another vice, gambling, where he claims to have lost anywhere from $50 to $60 million. These debts have taken most of Daly's professional winnings, sponsorship money, and forced him into doing corporate appearances to make ends meet.
Just this past week, Daly was seen at The Masters, not playing (he's still on suspension), but selling John Daly merchandise, out of a bus.
Also not helping the finances: Daly has been married (and divorced) four times.