In order to test these theories, I interacted extensively with nearly 50 of the most prominent executives convicted of white-collar offenses. Many of them had lost the confidence that they once displayed. Isolated from the business community that had placed them on a pedestal, many openly shared their views and perspective with me. Over the phone, by letter, and during visits to prison, I little by little began to better understand them.

At first, I was struck by their lack of remorse regarding either their actions or the harm those actions had caused. One executive even joked with me about how he’d been practicing with his $1,000-an-hour lawyer to convincingly, albeit falsely, express regret during his upcoming parole hearing. Troublingly, those who received lenient sentences for testifying against others often told me stories that differed from their sworn testimony.

Many of the convicted executives I spent time with described their conduct bluntly. “Morals go out the window when the pressure is on,” explained Steven Hoffenberg, who confessed to running a Ponzi scheme that stole from thousands of investors in his company, the Towers Financial Corporation. “When the responsibility is there and you have to meet budgetary numbers, you can forget about morals.” The reactions to engaging in crime were not always as I expected, either. David Myers, the former controller of WorldCom, recalled thinking that he was “helping people and doing the right thing” while perpetrating one of the largest accounting frauds in history. In his mind, the fraud was superficially sustaining the company, its stock price, and the jobs of its employees.

Some former executives defiantly denied that they did anything criminal. “I was in a good career making a couple million a year,” explained one executive who helped devise millions of dollars in illicit tax structures (and spoke on the condition of anonymity, given his continuing legal situation), “so it’s not that I’m going to risk everything to go do something shady or illegal.” Others felt that they were unfairly and selectively prosecuted for behavior that was ubiquitous in their industry. Most, however, accepted that they did something wrong. Yet, in spite of this recognition, it wasn’t clear even to the executives themselves why they made decisions that looked so thoughtless. After successful careers characterized by decades of careful decision-making, they found their own basic failures just as startling as others did.

When prosecutors try to explain white-collar misconduct, they often describe it as resulting from a cost-benefit calculation. A 1976 Wall Street Journal piece distinguished corporate crimes from other kinds of offenses by saying that “unlike the tempestuous and murderous spouse or the impoverished and desperate mugger, suite criminals are sophisticated and deliberative businessmen who engage in crime only after carefully calculating the benefits and costs.”