In case 1, Bernard Ebbers, CEO of WorldCom, rose from nothing to become a "telecom cowboy," before the 1990s downfall of WorldCom impacted thousands of investors. In case 2, Joseph Medawar is a television producer creating an action adventure series based on real-life national security cases, but the show is a scam to defraud investors of millions of dollars.

Once described as "The Most Aggressive CEO in America," Tyco's one-time CEO Dennis Kozlowski stole millions from the company for a lavish party, a gilded shower curtain, and fine art, before being incarcerated for white-collar theft. The episode documents Kozlowski's personal life in prison.