10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom

Larry Holzwarth - February 23, 2018

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
Bulger (left) and Flemmi intimidated drug dealers into paying for protection before moving into the market in Boston. FBI

The Boston Illegal Drug Trade

Both state and federal authorities were aware of Bulger’s control of most of the drug trade in Boston, but were unable to obtain sufficient evidence to make an arrest or build a case against him. Bulger controlled the drug market by threatening dealers with being killed if they did not co-operate with him, and his shakedown tactics brought most of the dealers to heel. Bulger at first did not involve himself in drug dealing beyond obtaining protection money and tribute. As the 1980s wore on he began to become more actively involved in the illegal drug trade.

Through the drug trade Bulger enhanced his mythical reputation of protecting the south Boston neighborhoods by refusing to allow heroin into the area. He also let it be known that his dealers were not to sell drugs to children. In truth, heroin was available in South Boston and Bulger was aware of it, he simply had his dealers concentrate on the sale of cocaine and marijuana.

When a major raid initiated by the Drug Enforcement Agency severely crippled South Boston’s cocaine market by taking most of the dealers off the streets, none of the arrested dealers would provide information to the authorities regarding Bulger’s involvement, out of fear of the retaliation the gang would launch. Fear of Bulger and his vengeance outweighed the sentences handed out by a court, and dealers were well aware that Bulger could reach them even in custody if he learned that they were making a deal with the authorities.

Efforts by investigators to develop evidence of Bulger’s involvement with the drug trade through surveillance using wiretaps was ineffective due to information received from the FBI via John Connolly and through the Massachusetts State Police. Bulger and Flemmi were aware of the dangers of being compromised by recorded phone conversations and avoided them as much as possible, preferring to discuss business face to face in open and ever changing locations.

Not until Bulger was on the run and both Weeks and Flemmi were providing information to the FBI and state officials was the level of Bulger’s involvement in the drug trade made evident. According to Kevin Weeks, Bulger’s profits from the sale of drugs and the shakedowns of drug dealers exceeded $30 million over the course of his involvement. Weeks also claimed that Bulger was finished with the drug business in 1990, following the DEA raid which crippled the cocaine market in the Boston area by sweeping up most of the major dealers.

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
Bulger murdered Flemmi’s girlfriend Debra Davis, and later the daughter of another Flemmi girlfriend, Deborah Hussey, by strangling them. CNN

Murders by strangulation

During Bulger’s trial in Boston his long-time associate and friend Stephen Flemmi told of standing by while Bulger strangled Deborah Hussey. Hussey was the daughter of Flemmi’s former girlfriend and he had known Deborah since she was a baby. Their relationship was such that Deborah called Flemmi “Daddy.” Flemmi also testified that he had had consensual oral sex with Deborah on two occasions, after her behavior had changed due to the abuse of drugs and engaging in prostitution in order to support her habit. It was the changed behavior which led Bulger to killing her.

Bulger was concerned that Hussey had become a liability to the Winter Hill gang because of her unstable behavior, which could lead to an arrest and then a deal with prosecutors. While working as a prostitute in Boston’s Combat Zone Deborah had taken to mentioning her close relationship with both Flemmi and Bulger, persuading gang members and others aware of their menace, to advance her money, drugs, or both. Bulger told Flemmi that she would have to be eliminated, and Flemmi agreed to bring her to him, in a house he had used to commit murders before (and in which bodies were buried in the basement).

Flemmi brought Deborah to the house, waiting outside the kitchen as Bulger strangled the 26 year old Hussey to death, which according to Flemmi, “…didn’t take long.” It was not the first time that Flemmi watched Bulger strangle a woman; four years earlier Bulger had strangled Flemmi’s then girlfriend, Debra Davis, to death, after which he told Flemmi to clean up his mess. Once the murder was complete Bulger went upstairs to lie down for a nap, which was customary for him following the act of murder.

Flemmi took the body downstairs to the basement and buried it in the floor, after first extracting the teeth to prevent identification via dental records. On the stand Flemmi admitted that he could not complete the task of removing all of the teeth, calling the job a “gruesome task.” He also removed her clothes to impede identification in the event the body was discovered. It was buried next to the body of Arthur Barrett, whom Bulger had murdered in the house by shooting him in the head years before, and Flemmi had buried him as well. After turning state’s witness Flemmi led investigators to the house and told them who was buried there.

It is impossible to know for certain how many murders were committed by Whitey Bulger. He was charged with 19 and convicted for 11. Given his proclivity for violence and his clear lack of remorse one can assume that there were more, and probably many more. After his years on the run a cult has arisen around him creating a legend of his being a sort of Robin Hood like figure in South Boston, preying only on fellow criminals, rather than innocent civilians, and protecting the community from the Italian mafia from North Boston. In fact, he preyed on anyone and anything, driven by his greed and his lust for violence.


Where did we find this stuff? Here are our sources:

“Six facts about Boston Gang Leader James “Whitey” Bulger”, by Tricia Escobedo, CNN, August 14, 2015

“Bulger on trial. The Complete Guide to Boston’s Most Notorious Gangster”, WBUR, wbur.org

“When Whitey Bulger was an FBI Informant”, by Patrick Keefe, The New Yorker, September 21, 2015

“Long Elusive, Mob Legend ended up a Recluse”, by Adam Nagourney and Amy Goodnough, The New York Times, June 23, 2011

“Silence earns mobster Whitey Bulger’s girlfriend 21 more months in prison”, by J. M. Lawrence, The Guardian, April 28, 2016

“Brutal: My Life in Whitey Bulger’s Irish Mob”, by Kevin Weeks

“A Criminal and an Irishman: The Inside Story of the Boston Mob-IRA Connection”, by Patrick Nee