John Rigas

Company: Adelphia Communications Corporation (1952 – 2006)

Biggest asshole moment: Robbing former employees of their retirement funds.

The Bernie Madoff of the tech world was indicted for stealing $100 million from his organization to fund other family-owned companies, causing massive layoffs and forcing Aldelphia to file for bankruptcy. He, along with sons Michael and Timothy, plus two other execs were also accused of concealing $2.3 billion in liabilities from investors and using corporate funds for their personal use. During the trial, former Century chairman Leonard Tow told the court he sold his company to Rigas and lost $1.5 billion he promised to charity before Adelphi’s stock crashed. Judge Leonard Sand added more salt to the wound by citing a letter from a former 70-year-old employee who lost his entire retirement fund, along with countless others. In an unjust verdict, Rigas was sentenced to 15 years in prison at the age of 80.