In 1986 over 400,000 Americans filed for bankruptcy. Their contribution to the USA’s growing debt crisis is indicative of the changing economic climate in the country. This study aims to uncover the legal, economic and social reasons for bankruptcy in America. Besides stories of single mothers, unlucky entrepreneurs, foolish investors and the suddenly unemployed, are the stories of those who deliberately attempt to manipulate the system through legal loopholes. The authors examine these stories from a moral, as well as financial, viewpoint and suggest legal reforms that could point to a way out of the economic jungle.