Fullback footballer for Liverpool; last played for Roma
Estimated lifetime earnings: $20+ million
Despite earnings topping $75,000 per week, this Liverpool soccer star declared bankruptcy in 2007 for unpaid debts. Embroiled in a dispute with his financial advisors and former agent, Einar Baardsen, over how his fortunes have been invested, the court has found evidence to link his case to a $4 million fraud investigation in Norway.