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Eight Business Lessons From Whitey Bulger

This 1953 Boston Police booking photo shows James “Whitey” Bulger after an arrest. Bulger was apprehended on June 23, 2001, in Santa Monica, Calif., after 16 years on the run.
This 1953 Boston Police booking photo shows James “Whitey” Bulger after an arrest. Bulger was apprehended on June 23, 2001, in Santa Monica, Calif., after 16 years on the run.Photograph by Boston Police/AP Photo

James “Whitey” Bulger, the 83-year-old head of South Boston’s feared Winter Hill Gang, accused of masterminding at least 19 murders, has been called a lot of things during his racketeering trial: a killer, a coward, a monster, and a rat. Nobody has called him a business genius, but as the trial goes on—it is now in its sixth week; star prosecution witness Stephen “Stippo” Rakes was found dead yesterday—it turns out that might be a little bit true.

“Whitey ran his business like a highly skilled CEO,” says Margaret McLean, a business law professor at Boston College and former Massachusetts assistant district attorney. For everything he’s done wrong (including “murder and mayhem,” according to prosecutor Brian Kelly), here are eight things that Whitey Bulger did entirely right: