Before Bernie Madoff, there was Ivan Boesky, the stock trader who used insider information to amass more money than he could never hope to spend but still enjoyed counting. In May of 1986, Boesky gave a speech in which he said, “I think greed is healthy,” and perhaps Oliver Stone should have given him a screenwriting credit for Wall Street. Only months after that address, Boesky was ruined, the cover boy of outraged articles about Wall Street’s brazen malfeasance. If there was a lesson learned, it was soon forgotten. From People in 1986:

“The unmasking of Ivan Boesky—a man who has come to symbolize unbounded avarice—has unsettled the financial community because no one knows who else may be under investigation. It has also led to some belated soul-searching about the ethics of Wall Street. In a commencement speech last year at the School of Business Administration at Berkeley, this is what Boesky had to say about greed: ‘I think greed is healthy. You can be greedy and still feel good about yourself.’ 

Even at the end, when the Securities and Exchange Commission scuttled Boesky’s operation, he still managed to cut himself a deal. It is widely believed that he agreed to record his phone conversations and thus implicate an unknown number of unscrupulous traders. He was allowed to unload an estimated $1.6 billion worth of stocks before the announcement of the government’s charges against him could drive prices down. 

Until November, Ivan F. Boesky was a glittering success. He had an ideal family—a handsome wife and four children—and lived in a $3.3 million mansion in New York’s affluent Westchester County. He gave lavishly to charity; he supported both the Republican and Democratic establishments—in short, he appeared the perfect gentleman from sole to crown. 

If there was an unresolved mystery about him, it was the quirky drive of someone who had wealth like water, yet who still lived as though he worked in a sweatshop. He slept a mere two hours a night. ‘The machine doesn’t like to stop,’ he explained to an interviewer two years ago. 

The son of a Russian immigrant delicatessen owner in Detroit, Boesky had a restless, floundering youth, dropping in and out of college, unable to land a satisfying job even after he graduated from the Detroit College of Law at 27. But he married well. Seema Silberstein was the daughter of real estate tycoon Ben Silberstein. Muriel Slatkin, Seema’s sister, has said her father had a low opinion of Boesky, who he said had ‘the hide of a rhinoceros and the nerve of a burglar.'”