In spite of United States boycott of Iran, Rich traded with the Ayatollahs government even while Americans were being held hostage in Tehran. It would be one of a series of distasteful (and in most cases, illegal) moves: he would do business with Libya, South Africa, Cuba and other countries under embargo or boycott. And it paid off: Rich made billions.
Apparently comfortable with his own business practices, Rich flouted tax laws as well. In 1983, Rich was indicted on 65 criminal charges, including tax fraud. He was said to have evaded at least $50 million in federal taxes, leading former New York Mayor Rudy Giuliani to remark that it was the biggest tax evasion case in US history. His company eventually handed over about $200 million in civil penalties but Rich and his business partner avoided prosecution and up to 300 years in prison by fleeing to Switzerland.
Even as the Internal Revenue Service offered huge rewards for his capture, Rich hardly suffered. Fortune magazine reported that after he fled, he continued to bring in millions, earning roughly $300 million in 1988 alone. His parties were lavish and legendary, ranging from a New Years Eve bash at his St. Moritz ski house to entertaining celebrities at his $9.5 million manse in Marbella, Spain.
Nearly two decades later, Rich was at the center of one of the most controversial presidential pardons in history. Even though he appeared on the FBIs Most Wanted list alongside Osama bin Laden, Rich was pardoned by then President Clinton in 2001.