Ivan Frederick Boesky was born in Detroit, Michigan to a Jewish family. He attended the Cranbrook Kingswood School in Bloomfield Hills before graduating from Detroit's Mumford High School. He then attended courses at Wayne State University, Eastern Michigan University and the University of Michigan. He was admitted to the Detroit College of Law, which allowed him to enroll despite having no undergraduate college degree. He graduated from the Detroit College of Law in 1965. In the 1980s, he served as an Adjunct Professor at Columbia University's Graduate School of Business and at New York University's Graduate School of Business.
Boesky's wife Seema was the daughter of real estate magnate Ben Silberstein, and the Silberstein fortune helped Boesky start his own arbitrage firm in 1975. By 1986, Boesky had become an arbitrageur who had amassed a fortune of more than $200 million by betting on corporate takeovers. These stock acquisitions were sometimes brazen, with massive purchases occurring only a few days before a corporation announced a takeover. The U.S. Securities and Exchange Commission (SEC) investigated him for making investments based on tips received from corporate insiders, and on November 14, 1986, SEC charged Boesky with illegal stock manipulation based on insider information. Boesky was featured on the cover of TIME December 1, 1986.
Although insider trading of this kind was illegal, laws prohibiting it were rarely enforced until Boesky was prosecuted. Boesky cooperated with the SEC; as a result of a plea bargain, Boesky received a prison sentence of 3.5 years and was fined $100 million. Although he was released after two years, he was barred from working in the securities business for the remainder of his life. He served his prison sentence at Lompoc Federal Prison Camp near Vandenberg Air Force Base in California. He served two years of his sentence and was released in 1990.
Boesky never recovered his reputation after doing a stint in jail and paying hundreds of millions of dollars in fines and compensation for his Guinness share-trading fraud role and a host of separate insider dealing scams. In later years he embraced his Judaism strongly and even took classes related to Judaism at the Jewish Theological Seminary of America where he was previously a major donor; however, in 1987, following the fallout from his financial scandal, The New York Times reported that "after Ivan F. Boesky had been fined $100 million in the insider-trading scandal, the Jewish Theological Seminary, acting at his request, took his name off its $20 million library."
His involvement in criminal activities is recounted in the book Den of Thieves by Pulitzer Prize-winning author James B. Stewart.
The character of Gordon Gekko in the 1987 movie Wall Street is based at least in part on Boesky, especially regarding a famous speech he delivered on the positive aspects of greed at the University of California, Berkeley in 1986, where he said, in part, "I think greed is healthy. You can be greedy and still feel good about yourself".
In the 2001 film Ocean's Eleven, Brad Pitt's character, Rusty Ryan, mentions a type of confidence scam termed "a Boesky" that involves a wealthy bankroller with insider information.