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
Catherine Grieg was Bulger’s companion for most of his time on the run. Years before she had been married to the brother of one of his murder victims. US Marshal Service

Life on the Lam

One of the areas of curiosity about Whitey Bulger is how he spent sixteen years eluding the authorities. During his years as a fugitive rumors arose from time to time, especially in the south Boston neighborhoods which regarded him as their own. One rumor had him fleeing to Ireland, where his former allies in the IRA were sheltering him from the prying eyes of the authorities. Another had him in Brazil. Clearly Bulger had prepared for the day he needed to run and was ready when it finally came. Nearly all of the time he spent on the FBI’s Ten Most Wanted list was idled away in Santa Monica.

Lindsey Cyr, Bulger’s former girlfriend and the mother of his son received annual visits for interviews with the US Marshals during Bulger’s absence, and reported hearing from him from time to time, the last time being in 2003. She was not told his location, and when the Marshal’s informed her that Bulger was running out of money she indicated that she doubted the assertion. Cyr claimed that Bulger had millions of dollars in cash stashed at various locations, and several passports. When he was found Bulger did claim to be nearly out of money, until investigators found several hundred thousand dollars hidden in the walls of his apartment.

Bulger did travel extensively during his first few years on the run, at first accompanied by Theresa Stanley, a girlfriend at the time of his flight. After she tired of life on the run he returned her to Boston and was joined by Catherine Grieg, whose former husband had been Bobby McGonagle, brother of Donald McGonagle, killed by Bulger years earlier. During their travels they visited Alcatraz as tourists, and Bulger had a photograph of the couple taken while they posed in prison garb. He told authorities once captured that they traveled to Europe and Mexico before settling in Santa Monica as a retired couple.

Grieg did all of the shopping, which was not an unusual sight in the area, where there were several elderly couples and retirees. A convalescent home was across the street from their Santa Monica apartment, which was rent controlled. In short, Bulger wasn’t seen very often by other than his immediate neighbors, and over time even that was less and less. Usually when Grieg left the apartment it was very early, and the couple presented themselves as sedentary retirees, asking few questions and avoiding social settings where they were likely to be asked.

In the end it was Grieg who led the FBI to Bulger. From interviewing her family and former friends the FBI learned that she was fastidious about her appearance, including her teeth, and had had cosmetic surgery in the past. The FBI focused its search for her using trade magazines and newsletters from the American Dental Association. It also produced a public service announcement which it ran just before receiving the tip which led them to Bulger. The PSA asked viewers to be on the lookout for the couple, and after sixteen years of hiding, Bulger was found following a tip received from a former neighbor.

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
A wanted poster for former Winter Hill Gang leader James J. Bulger. Massachusetts State Police

The Winter Hill Gang

During the early 1970s the Winter Hill gang – named for the Winter Hill neighborhood of Somerville – took over several gambling operations run by rivals by killing their operators. Afterwards, inept management of the operations by its new owners caused the gang to lose, rather than gain, large amounts of money. By the late 1970s the gang was forced to borrow money from the Italian Patriarca crime family and to raise enough money to pay the interest on the loans the gang began fixing horse races at tracks in New England.

FBI investigators built a case against most of the members of the Winter Hill gang, including Bulger and Flemmi, and Massachusetts State Police also were preparing indictments against them. Prosecutors were persuaded not to indict either Bulger or Flemmi (by John Connolly) and they were named as unindicted co-conspirators when more than two dozen of the Winter Hill gang were charged with racketeering for fixing races. With nearly all of the Winter Hill gang behind bars, Bulger and Flemmi took over the remnants.

Having seen the cost of gambling operations and their potential pitfalls, Bulger disassociated himself and the gang from directly operating gambling, and focused instead on protection of other bookmakers and numbers rackets. He also shook down and intimidated those gamblers who did not avail themselves of his services. Bulger and Flemmi continued to feed information to the FBI and enjoy its protection as they developed cases against the Patriarca family. By the mid-1980s the Patriarca family had been all but destroyed by the FBI investigations into their operations, leaving the door open for Bulger and Stephen Flemmi to control all of the organized crime in Boston.

During the 1980s, while working with Connolly, Bulger was personally involved in several more murders, including the icepick stabbing of Louie Litif, a bookmaker and cocaine dealer. Bulger was widely believed by mob associates to have carried out this murder himself, stabbing the victim with the icepick and then shooting him in the mouth, after which the body was stuffed in a trash bag in the trunk of his car. The killing was in retaliation for Litif’s not paying Bulger a cut from the profits of his cocaine dealing and for allegedly committing two murders without Bulger’s permission.

Later a witness came forward to inform the FBI that he had seen Bulger and Flemmi murder Litif. The witness was a cocaine dealer who offered the information to the FBI in return for an opportunity to enter the witness protection program. The cocaine dealer was named Edward Halloran, known on the streets as Balloonhead, and also had information linking Bulger and Flemmi to the murder of Roger Wheeler. FBI agent Connolly and his supervisor John Morris ensured Bulger was informed of Halloran’s dealings with the FBI.

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
Two died when Bulger learned that a former associate was at Anthony’s Pier 4 in South Boston. US DOJ

Murder of Edward Halloran

In May 1982 Whitey Bulger and Stephen Flemmi were informed that Edward Halloran, who went by his middle name of Brian, had been meeting with the FBI out of town, and was back in South Boston. Bulger sent Kevin Weeks to find Halloran and keep watch on him while he and another man – likely an associate of Bulger’s named James Flynn but possibly Patrick Nee, who denied involvement – armed themselves. Weeks learned that Halloran was having dinner at Anthony’s Pier Four, at the time one of the most financially successful restaurants in New England. It was located in South Boston.

Bulger and his accomplice waited in the parking lot in a car. Both men were in disguise. Bulger carried a rifle, his accomplice was armed with a MAC 10, equipped with a suppressor. A MAC 10 is a machine pistol capable of a rate of fire exceeding 1,000 rounds per minute while the suppressor both lessens the noise of firing and makes the weapon easier to control while firing. Bulger also carried a walkie-talkie, allowing him to communicate with Weeks, who was in a position to watch the door and Halloran’s movements.

Inside the restaurant Halloran encountered Michael Donahue, a friend of his. They had not planned on meeting and when Halloran explained that he had not driven to the restaurant Donahue offered him a ride home. Donahue was a truck driver by trade and a member of the Teamsters and other than his acquaintance with Halloran had no known connections with the Winter Hill gang or any other criminal activities.

When Donahue and Halloran left the restaurant, Weeks informed Bulger that Halloran was moving, using the message over the walkie-talkie, “The balloon is up,” a reference to Halloran’s nickname of Balloonhead. Once they were in Donahue’s car Bulger and the other gunman opened fire, with the MAC 10 rounds riddling the car. Donahue was hit in the head and died instantly. Halloran was badly wounded, but survived long enough to inform the authorities that his assailant had been James Flynn. He did not identify Bulger as the second killer.

When Stephen Flemmi turned government witness he stated that Patrick Nee, a Winter Hill associate and IRA member, had been the gunman. Kevin Weeks on the other hand claimed that Bulger had been one of the gunmen. James Flynn was arrested and tried for the murder; he was acquitted. A civil trial later established that the federal government had been responsible for the murder of Michael Donahue and Edward Halloran, through the actions of Connolly and Morris, who provided information regarding Halloran’s whereabouts to the killers.

10 Heinous Crimes of Whitey Bulger and His Organized Crime Kingdom
Kevin Weeks called contacts within the Massachusetts State Police even more valuable than those in the FBI. Massachusetts State police

Richard Schneiderhan and the Massachusetts State Police

Besides receiving information from the FBI through John Connolly and his supervisor, Bulger relied on information from the Massachusetts State Police. In interviews, long-time Bulger associate Kevin Weeks has repeatedly stated that the information received from the Massachusetts State Police was far more valuable to Bulger in pursuit of his criminal activities and his avoidance of arrest for so many years, despite the number of crimes attributed to him. Information from the Massachusetts State Police came directly from the District Attorney’s Organized Crime Unit.

Richard Schneiderhan was an investigator with the Massachusetts State Police and over a period of ten years when he worked within the Organized Crime Unit he rose to become its Chief Intelligence Officer. This placed him in a position from which he worked with prosecutors, other investigators, and federal officers as part of the overall effort to eliminate organized crime in Massachusetts, and especially in Boston. As a liaison between agencies, he was in a position to be aware of the efforts of other investigating agencies, fostering an atmosphere of co-operation between the state and federal efforts.

Schneiderhan was in contact with Stephen Flemmi, and provided Flemmi with information regarding ongoing investigations, including the presence of wiretaps, which Flemmi passed on to Bulger. Schneiderhan was also in contact with Kevin Weeks. How the gangsters compensated Schneiderhan has never been established. It is widely believed that Schneiderhan accepted cash payments for the information, although that charge has never been proved by the authorities. Schneiderhan was a long-time friend of Flemmi’s and it is possible that he provided the information out of friendship alone.

When the FBI put both of Bulger’s brothers under telephone surveillance through wiretaps, Schneiderhan passed the information along to Kevin Weeks, who in turn passed it to Bulger. It was Weeks who later gave the grand jury information which incriminated Schneiderhan, as part of the former’s deal to co-operate with the authorities following his own indictment and Bulger’s disappearance. Schneiderhan had by then been long retired, but he maintained contacts with the FBI, the Massachusetts State Police, and both Flemmi and Weeks.

Schneiderhan was charged with obstruction of justice and conspiracy after his role supplying information to the Winter Hill Gang became known, and was sent to federal prison. Because it was determined that the crimes for which he had been convicted occurred after his retirement he continued to draw his pension from the Massachusetts State Police following his conviction. He was released from prison in 2006 and died in 2015. He was never charged for providing information while active with the State Police, although Kevin Weeks claimed his services were of much more value to the gang than those of the FBI.

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