Insider trading scandals on Wall Street have focused public attention on the abuse of money and power in the service of greed. The analytic situation described in this paper involves a patient who was involved in a major white-collar crime in the 1990s and imprisoned on charges of fraud. Release from prison brought his anxieties about money, work, and masculinity into sharp focus. The paper explores the some of the emotional conflicts and confusion around corporate success and failure, and the particular issues that arise when people identify themselves with the company they work for, something that corporate culture has always encouraged.