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1. David James

Finishing his footballing career in the depths of Iceland may not have been the smartest move, but former Liverpool goalkeeper David James saw his illustrious career literally stop short. Having played both for Portsmouth and appearing at the FIFA 2010 World Cup for England, James was a major figure in the game. He played for more than two decades and also pulled on the jersey for Aston Villa, West Ham United and Manchester City. His career earnings saw him bring in more than $30 million which saw him strut his stuff as a model for fashion label Armani. In 2005, James needed the funds in order to settle a costly divorce and later filed for insolvency this year.
2. John Arne Riise

3. Celestine Babayaro

4. Eric Djemba-Djemba

5. Brad Friedel

Iconic American goalkeeper Brad Friedel was one of the best no.1’s around, especially in his home nation. With successful spells at both Aston Villa, as well as Tottenham the former US no.1 was earning a fair wedge between the sticks. Yet, in 2011, Friedel had actually been declared completely bankrupt back in the United States. His football academy based in Lorain, Ohio was spiralling debts of around $7 million. In fact, most were not willing to subscribe thanks to its hefty $50,000 annual subscription which led to the banks repossessing his home.