This chapter presents an overview of that failure as a cautionary tale, with a particular focus on the role of the lawyers and the corruption of values that occurred. The circumstances of collapse of Enron, a major American corporation, involve complex factors that were investigated from many vantage points. Enron and its lawyers sought to employ a financing technique often referred to as “structured finance,” based upon an accounting rule that allowed for sale of a partial interest in an asset to a partnership where the seller retained an interest and a measure of continued management. In the Enron case, the Bankruptcy Court appointed an independent Examiner to review the role of the parties to the accounting-driven “off balance sheet” transactions, which were integral to the financial manipulations and misstatements of financial conditions of Enron. In certain hedging transactions in commodity and energy transactions, the term “total return swap” is used to balance out the final settlement of the transactions.