Era: Late 1980s
Before Dick Fuld and Dick Grasso, AIG and Enron, and every other poster boy for Wall Street greed and excess, there was Michael Milken, the junk-bond king of Drexel Burnham. Milken was a financial genius and a pioneer—“high-yield bonds” were revolutionary, a high-risk, high-reward way for companies to raise money. But used recklessly, they were a tool to tear apart otherwise healthy companies—the era of the hostile takeover was on. And even after a staggering $550 million bonus in 1986, Milken couldn’t help himself—he was convicted of securities fraud, part of Ivan Boesky’s insider-trading ring. Boesky was the inspiration for Gordon “Greed is Good” Gekko, but it was Milken who epitomized the iconic ‘80s Wall Street villain. Milken served nearly two years in prison, and Drexel Burnham went kaput.