On October 23, 2006, a judge sentenced Jeffrey Skilling, head of energy-trading giant Enron, to 24 years in prison after his company went bankrupt and he was convicted of fraud. The judge accused Skilling of gross deception and withholding information. Gladwell, however, judges the nature of Enron’s deception to be more a mystery than a puzzle, one that will not reach a satisfying conclusion regardless of how much information we have about the convicted party’s activities. He notes that the national-security expert Gregory Treverton makes the distinction that while puzzles can be solved by having all the factual information, mysteries require discernment to evaluate what is important out of too much information. Gladwell cites the example of the employment of diverse crews of analysts during World War II to filter the overwhelming amount of Nazi propaganda into more concrete indications of their actual intentions.

Enron was involved in myriad forms of financially precarious activity, such as making loans to higher-credit-risk consumers and then speculating on up to 747 million dollars of unrealized money in the second quarter of 2000, in addition to undue reliance on special-purpose entities, or SPEs, which use partnerships with investors at times when a company is in trouble to raise capital without increasing indebtedness or risking high-interest-rate lending from banks.