#3 Brad Friedel
American goalkeeper Brad Friedel was a part of several Premier League teams and was arguably one of the most famous American exports to England. Despite being on a paycheck of over £40,000 a week while at Aston Villa, the goalie was declared bankrupt after it was found that he had debts of over £5 million.
This happened back in 2011 in the United States where it was found that the player's non-profit football academy had bundled up debts which it was unable to pay. Friedel had opened this football academy in his home state of Ohio and had taken loans from RBS Citizens.
The financial institution took Friedel to court over the loan and the proceeding started from there. This is not all as the lender also decided to take over his house which had a value of over £260,000.
Friedel has since then retired and was last seen as an assistant coach for the US U-20 team.