Arbitrageur Ivan Boesky paid a $100 million penalty in 1986 for insider trading — the largest ever at the time. Months earlier he had told a graduating class that “greed is healthy,” the line that inspired Gordon Gekko’s “greed is good.”

Michael Milken built the junk-bond market of the 1980s, then pleaded guilty in 1990 to securities and tax felonies and paid $600 million in fines. He was banned from the securities industry for life — and pardoned by President Trump in 2020.