Boesky was born to a Jewish family in Detroit. His family owned several delicatessens and taverns in the city. Although he lacked an undergraduate degree, he was admitted to Detroit College of Law (now Michigan State University College of Law) and graduated in 1965. In the 1980s, Boesky served as an adjunct professor at Columbia University's Graduate School of Business and at New York University's Graduate School of Business.

Time magazine ran a December 1, 1986, cover story about his "scam," dubbing him "Ivan the Terrible."[11]

Per a plea bargain, he received a prison sentence of 3+1⁄2 years and was fined US$100 million. Although he was released after serving only 20 months, he was permanently prohibited from working with securities. He served his sentence at Lompoc Federal Prison Camp near Vandenberg Air Force Base in California.

Boesky smoked Marlboro cigarettes and lived till 87 yrs.

Boesky was also featured in Titans The Rise of Wall Street on Amazon Prime