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.

Bulger on trial

“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. Nobody would argue that Bulger is a good or moral person, but as someone who ran one of the most successful crime operations in the U.S. during the 1970s and 80s, he probably has a few business tricks up his sleeve. For everything he’s done wrong (among them “murder and mayhem,” according to prosecutor Brian Kelly), here are eight things that Whitey Bulger did entirely right.


Landing an executive-level job with the Winter Hill Gang during the 1970s was tougher than getting hired by Google today. “He let very few people into his inner circle,” says Dick Lehr, co-author of Whitey: The Life of America’s Most Notorious Mobster. His applicant interview process could take years. To wit: He watched White Hill enforcer Kevin Weeks grow up in South Boston, followed his career as a bouncer at a local club, and knew everything about him before bringing him on, McLean says.

Bulger used this same patience when firing (i.e. murdering) employees. John Callahan, a longtime Bulger associate, was only let go after an extensive cost-benefit analysis. Bulger brought his closest associates, Stephen “The Rifleman” Flemmi and John “The Executioner” Martorano, to New York to debate the matter. “He wouldn’t kill anyone on a whim,” says McLean. “Bulger wanted to be sure he was making the right decision.”


Weeks, Bulger’s one-time lieutenant, told Ed Bradley that killing somebody was relaxing for Bulger. “He’d be nice and calm for a couple weeks afterwards.” You can’t make an argument for murder, but you can for choosing a career path where you relish the challenges rather than dread them. “In the workplace, attitude is everything,” says Dr. Mark Pfeffer, director of the Chicago-based Panic/Anxiety Recovery Center. While we may be hard-wired for productivity, very few people find jobs that perfectly match their personalities. “The trick,” Pfeffer says, “is to create something in your work zone that fills a need inside of you.” For Bulger, it was killing people. For you, hopefully something less murdery.


During his trial, Bulger hasn’t soft-pedaled his feelings for his employees. During Weeks’ testimony, Bulger interrupted his former protégé to tell him “You suck!” During testimony by John Morris, an ex-FBI agent on Bulger’s payroll, the crime boss snarled, “You’re a fucking liar.” Managers could learn a few things from Bulger’s willingness to communicate his displeasure, says Deborah Grayson Riegel, a behavior and communication expert and author of Oy Vey! Isn’t a Strategy. “They need to lose the ‘sandwich feedback’ technique,” she says—wherein negative feedback is buttressed by positive comments. Bulger’s outbursts, while crass, were a step in the right direction. It’s a better approach, Riegel says, than the tap dance of “You’re doing a fantastic job and we’re so lucky to have you, but…”


Photos from Bulger’s apartment, released by the U.S. Attorney’s office shortly after his arrest in 2011, reveal a large collection of nonfiction books about gangsters and crime, including True Stories of Law & Order, The Last Gangster, Public Enemies and Escape from Alcatraz. The books weren’t just navel-gazing; many of them, like Secrets of a Back-Alley ID Man: Fake ID Construction Techniques of the Underground and The Worst Case Scenario Survival Handbook, were obviously homework for the gangster on the run. Despite a 70-year career in crime—Bulger was first arrested when he was just fourteen years old and charged with larceny—he felt he still had much to learn. Bulger, says Lehr, has always been an avid reader. “He was really interested in military history,” says Lehr. “He studied strategy, warfare, and conflict battle. He looked at it as self-educating himself and becoming a better leader and strategist.”


There’s a reason Bulger’s Winter Hill Gang has shuttered while other crime operations, like La Cosa Nostra, the U.S. Italian mafia, is still very much alive and well. “The LCN is run like a corporation,” says McLean. “You’ve got the CEO, the boss, the underboss, the consigliere, the soldiers. It’s not dependent on any one person. The top guys die off, and others come in to replace them.” Bulger, however, preferred a management style built on his cult of personality. “He was a supreme narcissist,” Lehr says. “It was all about him. So when he left, the organization collapsed.” There were no systems in place for replacing leaders, as Bulger couldn’t tolerate or fathom the idea of the Winter Hill Gang without him. “If you want your business to last, it shouldn’t be built as a reflection of yourself,” says Lehr. “You have to prepare for a time when you won’t be in charge anymore.”


One of the most chilling stories shared during the trial by prosecutor Brian Kelly concerned the 1984 murder of John McIntyre. Bulger’s original plan was to strangle McIntyre, whom he suspected of being an informant, but the rope he brought was too thick to do the job. “You want one in the head?” Bulger allegedly asked his victim. McIntyre agreed, and Bulger shot him instead. A horrifying tale at face value, but as a business metaphor, it’s a great reminder that things don’t always go according to plan. “Bulger was demonstrating an unyielding commitment to his goal,” says Riegel, “and a willingness to consider multiple paths to getting there.” When his original idea failed, he didn’t get frustrated or obstinate. Instead, he tried something else, and even asked his victim for advice. “Managers need to be flexible in the face of change,” says Riegel.


Bulger may’ve had a reputation for being ruthless and cruel with rivals, but in his South Boston neighborhood, he was known as a generous local businessman who didn’t hesitate to help the less fortunate. According to Lehr: “As a teenager, he was the guy who helped mothers across the street with groceries. In the 70s and 80s, he’d give food or money to families in need. He believed that if you took care of your neighbors, they’d protect you, or at least not add to your bad press.” After his capture in 2011, a woman from Bulger’s old Boston neighborhood told the New York Times that many locals thought the mob boss “was like Robin Hood.” “There’s something to it,” Lehr says of Bulger’s community outreach. “Even now, after everything people know about Whitey and his crimes, the locals still talk fondly about him. They still think he’s a good guy.”


After his arrest in 2011, Bulger was taken to a federal courthouse in Boston, where he was asked if he could afford the cost of a lawyer. “Well, I could if you’d give me back my money,” he quipped. (According to feds, he had over $800,000 in cash in his Santa Monica apartment.) Bulger often cracked jokes during even the most tense situations. It’s telling that many of his former employees have at least one tale of Bulger’s wit. “Most of us respect a boss who takes us, the work and the mission of the organization seriously, without taking him or herself too seriously,” says Riegel. “In particular, self-directed or self-deprecating humor, used sparingly but strategically, can go a long way to reduce tensions, level the playing field, and demonstrate authenticity.”

(This story originally appeared, in a slightly different form, in Bloomberg Businessweek.)