Bulger stuffed guns and cash into the walls of his Santa Monica apartment.
Whitey Bulger reportedly committed his first murder in 1969 at the age of 40, which marked him as a late bloomer in the killing business. In 1979, following years of internecine warfare among South Boston’s Irish crime clans, Bulger assumed control of the Winter Hill Gang, becoming the community’s undisputed overlord of drug dealing, loan-sharking, gambling, and extortion. His headquarters was the Triple O’s Lounge; when its owner complained that he could lose his license because of Bulger’s activities there, the mobster shot back, “You could lose your life.”
Born in the Crash year of 1929, Bulger was the son of a hard-luck laborer and a homemaker. He grew up handsome and with a distinctive shock of blond hair that inspired the nickname he detests; associates addressed him as Jim or Jimmy. As a teenager he had briefly run away with the Ringling Brothers Circus. Bulger fought his way out of both slum life and the repressive Catholic culture that dominated existence in the public housing projects he lived in, moving from petty larceny in the 1940s to armed robbery to extortion. Following a 1956 conviction for a bank heist, he served nine years of a 20-year sentence in Alcatraz, Leavenworth, and other federal penitentiaries before appeals from Father Robert Drinan, a family friend and future congressman, helped win his early release.
Serving time in Atlanta during the early part of his confinement, Bulger sought to lessen his sentence by volunteering for covert CIA-sponsored medical experiments with LSD. They proved to be horrible experiences “followed by thoughts of suicide and deep depression,” he’d later write in his diaries, adding, “I was in prison for committing a crime and feel they committed a worse crime on me.”
In the 1970s, Bulger fought Boston’s attempt to integrate its public schools by busing black students to predominantly white schools. Bulger set fire to John F. Kennedy’s birthplace and firebombed an elementary school. He also sent shotgun blasts into the Boston Globe building and tried to have Plymouth Rock blown up, though the Pilgrim landmark was barely scratched. A decade later, he fancied himself a soldier in another war, organizing a shipment of arms to the Irish Republican Army. The weapons were seized by the Irish navy, and several arrests were made.
With his ascent, neighborhood mythmaking began casting Bulger as a modern Robin Hood who handed out free turkeys on Thanksgiving and gave Southie’s elderly rides in his car. He wouldn’t let hard narcotics into the community, went the stories, and he let it be known that his code of honor forbade him from hurting women. To South Bostonians Bulger represented a form of traditional neighborhood values. “I’m an old-school guy,” he told Josh Bond at the Princess Eugenia. “Where I grew up, Italians didn’t mix with Irish.”
Money was never a problem for the Winter Hill crew. If he needed cash, Bulger would order a bookie, a drug dealer, or sometimes an innocent civilian to appear in his office above the Triple O’s. Pointing to a black body bag, he would tell the visitor that he, Bulger, had been contracted by the Mob to kill the individual—and would—unless the guy paid him $50,000. The man would be sent on his way, a walking hostage who had to raise his own ransom.
“He had these laser, piercing blue eyes—they burned holes in you as though he was pure evil,” says Steve Davis, who found himself summoned by Bulger one day in 1982. Davis, 55, describes himself at the time of that meeting as a “street hustler.” His sister, Debra, had been the girlfriend of Bulger’s longtime associate Stephen Flemmi until she suddenly disappeared from Southie the year before. “I thought I was dead,” Davis remembers. “He asked me for money, and I wouldn’t give him any.” Although Davis left with his life that day, Bulger handed him a bullet as a reminder of his “debt.”
Not so lucky was Debbie Hussey, the 26-year-old daughter of Flemmi’s live-in mistress. Dubbed “The Rifleman,” Flemmi was a serial philanderer who had sexually molested Hussey since the time she was an adolescent. After Hussey matured into a drug-addicted prostitute, Bulger convinced Flemmi that she had become a liability who needed to be killed.
So one night Flemmi lured Hussey into an unoccupied house, where Bulger attacked and strangled her. To make sure she was dead, Flemmi reputedly applied a tourniquet around her throat, tightening a rope with a stick. Then Bulger lay down, as he often did following a murder, to nap while Flemmi removed Hussey’s teeth with pliers to make her corpse more difficult to identify. (Davis’s sister, it turned out, had allegedly been dispatched in a similar way.) Flemmi and two other associates buried Hussey in the basement. Months later they had to dig up and rebury her—along with two other rotting bodies—because the home had gone on the market.
Hussey’s murder didn’t make it into The Departed, the 2006 Martin Scorsese film inspired by Bulger. In that film Jack Nicholson’s Irish Mob boss dies in an appropriately cinematic shoot-out, while Bulger was living an exceedingly uncinematic life at the Princess Eugenia, a half-hour drive from Nicholson’s home in the Hollywood Hills. Santa Monica was the biblical opposite of the South Boston Whitey Bulger had known as a child and as a crime baron. Not many American gangsters live long enough to choose where they retire. With its temperate climate and reputation for relaxed living, the seaside town must have seemed like a paradisiacal reward for surviving his opponents on both sides of the law in scruffy Southie.
Santa Monica offered Bulger priceless anonymity. Thousands of miles from Boston, it’s a city where the very notion of organized crime seems like National Geographic exotica. Ask someone there—or anywhere else in Los Angeles—to identify a real-life local Mob boss and you’ll be lucky to get the long-gone Bugsy Siegel or Mickey Cohen; for residents of New York, Boston, and Chicago the name of the current local Mafia don is as familiar as the mayor’s, the police chief’s, or a cardinal’s.
This feature originally appeared in the October 2013 issue of Los Angeles magazine