Stephen "The Rifleman" Flemmi

Stephen Joseph "The Rifleman" Flemmi (born June 9, 1934) is an Italian-American mobster and close associate of Winter Hill Gang boss James J. Bulger. Beginning in 1965, Flemmi was a top echelon informant for the Federal Bureau of Investigation (FBI). Despite delivering a great deal of intelligence about the inner workings of the Patriarca crime family, Flemmi's own criminal activities proved a public relations nightmare for the FBI. For this reason, he was prosecuted under the Racketeer Influenced and Corrupt Organizations Act (RICO) and sentenced to a long term of incarceration.

Early years

Stephen Joseph Flemmi was the eldest of three sons born to Italian immigrant Giovanni and Mary Irene Flemmi. He was raised in the Orchard Park tenement located at 25 Ambrose Street in Roxbury, Massachusetts. His father was a bricklayer and veteran of the Royal Italian Army during World War I, and his mother was a full-time homemaker.

Flemmi is described by his former mistress Marilyn DeSilva as mild mannered and personable. He was a childhood friend and mentor of Richard J. Schneiderhan, who later became a lieutenant in the Massachusetts State Police.

Flemmi was raised while a child as a Roman Catholic, but unofficially converted to Jehovah's Witness while incarcerated in 1981.

Criminal career

After the end of the Korean War, Flemmi and his brother Vincent joined the crew of Portuguese-American mobster Joseph Barboza. Barboza had close ties to both the Patriarca crime family of Providence, Rhode Island and the Irish-American Winter Hill Gang of Somerville, Massachusetts.

In the early 1960s, a gangland war broke out on the streets of Boston after George McLaughlin, the younger brother of the Charlestown Mob's boss, groped the girlfriend of a ranking Winter Hill member. In retaliation, McLaughlin was severely beaten and left for dead. Enraged, his brother demanded that Winter Hill boss James "Buddy" McLean sanction the murders of the men responsible. McLean refused, saying that McLaughlin's actions were "out of line". Enraged, the McLaughlins later attempted to wire a bomb under his car and were disrupted by McLean. More than 40 murders throughout the Boston area are believed to be linked to the resulting clash.

During the course of the war, the Barboza crew allied itself with Winter Hill and assisted in several contract killings.

In 1965, Flemmi was secretly recruited as a confidential informant by FBI Agent H. Paul Rico, giving the agency inside information about Boston's gangland. However, Flemmi allegedly used his informant status to get important members of the rival Charlestown Mob arrested and to protect his allies.

In 1967, after Barboza became a cooperating witness and disappeared into the fledgling Witness Protection Program, Flemmi and his partner Frank Salemme arranged the car bombing of Barboza's lawyer, John Fitzgerald, who was suspected of persuading his client to testify. Fitzgerald was severely injured, but survived.

In response, Flemmi and Salemme fled Boston. After Salemme was arrested in New York City in 1972, Flemmi fled to Montreal, Quebec.

In May 1974, Rico told Flemmi it was safe to return to Boston, which he did once the charges against him were dismissed. He moved back with his mistress, Marion Hussey, in suburban Milton, Massachusetts.

Relationship with James J. Bulger

In 1967, James J. "Whitey" Bulger was released from Federal prison after serving a nine-year sentence for robbing banks. After a few years of working as a janitor, he became an enforcer for South Boston mob boss Donald Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howie Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick Nee. Winter soon chose Bulger as his man in South Boston. Shortly afterward, Bulger became partners with Flemmi.

At this time, the Boston FBI office tried to convince Bulger to become an informant, but he refused.

Disgraced former FBI agent John Connolly (FBI), who grew up with Bulger in South Boston, always claimed that he reached an agreement with Bulger during a late night meeting inside an unmarked car. According to Flemmi, Bulger became an informant on his own and quickly learned of his partner's secret.

Bulger allegedly told Flemmi that he knew his secret. Flemmi has insisted that he did not know at the time that Bulger was also an informant. Kevin Weeks, however, insists that Flemmi's story is untrue. He considers it too much of a coincidence that Bulger became an informant a year after becoming Flemmi's partner. He has written of his belief that Flemmi had probably helped to build a Federal case against him. Weeks has said that Bulger was likely forced to choose between supplying information to the FBI or returning to prison.

However, Flemmi and Bulger were quickly able to turn their informant status to their own advantage. John Connolly, who had been assigned to keep an eye on them, soon came to look up to Bulger and viewed him like an older brother. Federal prosecutors have since stated that Connolly became a member of the Winter Hill Gang, allegedly supplying them with the names of informants and funneling bribes to at least one fellow agent.

In 1979, the U.S. Attorney indicted the leadership of the Winter Hill Gang, including boss Howie Winter, on extortion, gambling, and racketeering charges. Flemmi and Bulger were both listed as unindicted co-defendants. John Connolly had convinced prosecutors that his two informants were too valuable to prosecute. At that time, Irish-American gangsters were not the FBI's main concern; they wanted to destroy the Patriarca crime family. Then, as now, arrests and trials of Italian-American mobsters garnered considerable publicity. After the conviction of Winter and his associates, the leadership of the Winter Hill Gang devolved on Bulger, who chose Flemmi as his lieutenant. The pair moved the gang's headquarters to the Lancaster Street Garage in Boston's West End.

Ties to the Patriarca crime family

Although Bulger had some dealings with Gennaro Angiulo, the Patriarca crime family's underboss in Boston, he rarely spoke to the Italians personally, usually using Flemmi as a go-between. Through Vincent, he had become acquainted with his brother's handler H. Paul Rico, and as Vincent succumbed to heroin addiction in the late 1960s, Rico increasingly sought Stephen out for reliable information.

Flemmi was offered the privilege of becoming a made man, as was Johnny Martorano, another Winter Hill Gang member. However, Flemmi declined the offer from Angiulo and Ilario Zannino and stayed with the Winter Hill Gang.

At one point, Bulger and Flemmi took out a $200,000 loan from Angiulo. When Angiulo asked them about repayment, Bulger and Flemmi stalled him. Angiulo was infuriated and a serious gang war appeared imminent. However, Flemmi had already been describing the layout of the Angiulo's headquarters, which was inside a Prince Street tenement in the North End, Boston. In 1986, the FBI planted a bug in the building.

The murder of John McIntyre

Flemmi's second victim was John McIntyre, a 32-year-old drug smuggler of mixed Irish and German descent. Like many of Boston's Irish Americans, he was also an avid sympathizer of the Irish Republican Army. McIntyre had informed on the Valhalla arms trafficking deal between the Winter Hill Gang and the Provos. Like his first victim, Arthur "Bucky" Barrett, McIntyre was lured to the house and killed in the basement. Bulger shot McIntyre in the back of the head with a .22 caliber rifle, killing him instantly. Weeks and Flemmi buried McIntyre's remains just like they had done with Barrett.

Relationship with parents

In 1979 Flemmi's mother Mary was mugged in Mattapan, Massachusetts by a gang of African-Americans, and a photo of her sitting outside her car, on the pavement dazed and bloody, had appeared on the regional Associated Press wire. This infuriated Flemmi, who remained close to his ailing mother over the years. He felt the need to locate his parents to a nice, low crime neighborhood. After consulting Bulger, he was told that 832 East Third Street, next door to Bulger's brother William, happened to be up for sale. Flemmi's parents' house eventually became a place for him to meet with Bulger, Connolly, and Rico.

Married life

In the 1950s, Flemmi was married to an Irish-American woman named Jeanette, from whom he later became estranged. By 1980, he planned to divorce Jeanette to marry his longtime mistress, Marilyn DeSilva, but it is unknown whether he ever followed through with the legal actions. Throughout his life, Flemmi was engaged in clandestine affairs with several other women, including sisters Debra Davis and Michelle Davis and Deborah Hussey. Flemmi met Debra Davis at a jewelry store, and the couple dated for more than seven years. In 1981, Bulger is said to have killed Davis because she knew that Flemmi was an informant.

After his return to Boston, Flemmi began a common law marriage with Marion Hussey, a Boston divorcee with several children. With Marion he fathered two children, Stephen and Robert Hussey, and two daughters. He also became the stepfather of two daughters including Deborah, from a previous marriage. He bought Deborah Hussey a Jaguar when she turned sixteen, and later he set her up in an apartment in the Back Bay, even as he continued living with her mother in Milton. By the age of seventeen, his stepdaughter had dropped out of high school and gone from working as a waitress in Dorchester to working as a stripper and occasional prostitute in Boston's Combat Zone.

It is thought that Flemmi, Bulger, and Weeks lured her to the house at 799 East Third Street in South Boston and garrotted her. Her body was then buried in the basement. According to Kevin Weeks,

“Stevie said he'd take care of the clothes and the teeth. He was all business, going about the task of removing cleaning up and pulling teeth. Even though he had a long term relationship with Debbie, this wasn't bothering him any more than it had bothered Jimmy. Stevie was actually enjoying it, the way he always enjoyed a good murder. Like a stockbroker going to work, he was just doing his job. Cold and relaxed, with no emotion or change in demeanor, he was performing a night's work. Whether he went out to meet one of his girlfriends or home to Marion, I have no idea. Later on, when I was alone with Jimmy, I asked him what this was all about. 'Who knows?' he answered. 'She was bringing Blacks back to the house. She was doing drugs. Stevie was probably fucking her.' I never asked again, but it was just kind of distasteful killing a woman. I can see killing guys. That's the life they chose, the life they're involved in, the life we all chose. But a woman was different. It wasn't a nice thing. Years later, it came out that Stevie was in fact having sex with Debbie. And she'd been his stepdaughter since she was three years old. Who knows if she knew anything else about him? But to kill a woman because she threatened to tell that you were fucking her didn't make any sense, no more than it did to kill a girlfriend because she wanted to leave you. According to Stevie testimony in a later trial, when it came out that he had been having sex with her daughter, Marion tossed his clothes out in the driveway and changed the locks to the house. She didn't know about the murder, but she knew about the sex. That didn't make any sense either.”

Relationship with the FBI

Rico first recruited Flemmi as an informant in 1965.

In 1997, shortly after the Boston Globe disclosed that Bulger and Flemmi had been informants, former Bulger confidant Kevin Weeks met with Connolly, who showed him a photocopy of Bulger's FBI informant file. In order to explain Bulger and Flemmi's status as informants, Connolly said, "The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them." According to Weeks,

“As I read over the files at the Top of the Hub that night, Connolly kept telling me that 90 percent of the information in the files came from Stevie. Certainly Jimmy hadn't been around the Mafia the way Stevie had. But, Connolly told me, he had to put Jimmy's name on the files to keep his file active. As long as Jimmy was an active informant, Connolly said, he could justify meeting with Jimmy and giving him valuable information. Even after he retired, Connolly still had friends in the FBI, and he and Jimmy kept meeting to let each other know what was going on. I listened to all that, but now I understood that even though he was retired, Connolly was still getting information, as well as money, from Jimmy. As I continued to read, I could see that a lot of the reports were not just against the Italians. There were more and more names of Polish and Irish guys, of people we had done business with, of friends of mine. Whenever I came across the name of someone I knew, I would read exactly what it said about that person. I would see, over and over again, that some of these people had been arrested for crimes that were mentioned in these reports. It didn't take long for me to realize that it had been bullshit when Connolly told me that the files hadn't been disseminated, that they had been for his own personal use. He had been an employee of the FBI. He hadn't worked for himself. If there was some investigation going on and his supervisor said, 'Let me take a look at that,' what was Connolly going to do? He had to give it up. And he obviously had. I thought about what Jimmy had always said, 'You can lie to your wife and to your girlfriends, but not to your friends. Not to anyone we're in business with.' Maybe Jimmy and Stevie hadn't lied to me. But they sure hadn't been telling me everything.”

Arrest and imprisonment

In December 1994, Connelly informed Bulger and Flemmi that several imprisoned Jewish-American bookmakers had agreed to testify to paying them protection money. As a result, sealed indictments had come from the Department of Justice and the FBI was due to make arrests during the Christmas season. In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Catherine Greig.

According to Kevin Weeks,

“In 1993 and 1994, before the pinches came down, Jimmy and Stevie were traveling on the French and Italian Riviera. The two of them traveled all over Europe, sometimes separating for a while. Sometimes they took girls, sometimes just the two of them went. They would rent cars and travel all through Europe. It was more preparation than anything, getting ready for another life. They didn't ask me to go, not that I would have wanted to. Jimmy had prepared for the run for years. He'd established a whole other person, Thomas Baxter, with a complete ID and credit cards in that name. He'd even joined associations in Baxter's name, building an entire portfolio for the guy. He'd always said you had to be ready to take off on short notice. And he was.”

Flemmi, however, chose to remain in Boston and was swiftly taken into custody and incarcerated at the Plymouth County House of Correction. He believed he had protection, but not immunity.

With his lawyer, Flemmi planned to prove through the testimony of his self and others, that he had indeed had protection from the FBI, such that Judge Wolf would have no choice but to throw out the entire indictment. Stephen's problem was that he couldn't really come clean. Without immunity, he couldn't admit to killings he hadn't been charged with. And by the time Stephen took the stand, in August 1998, John Martorano had already started outlining the details of almost twenty murders he'd committed. Many of his murders had been done at the direction of Bulger and Stephen, who had paid him more than $1 million during his years as a wanted fugitive between 1978 and 1995. To many questions about the murders Flemmi was involved in, he pleaded the Fifth Amendment.

In 1999 Mary Flemmi died, and two of Stephen's illegitimate sons, born by Marion Hussey, decided to case the Winter Hill Gang's old headquarters on East Third Street. They discovered $500,000 in cash, which they spent over a period of a six-month shopping spree, as one of them later testified. The families of John McIntyre, Debra Davis, Brian Halloran, and Wimpy and Walter Bennett all filed civil suits against the U.S. Government, claiming that the FBI's protection of Bulger and Flemmi had resulted in the murders of their loved ones. In January 2003, Flemmi's brother Michael, then a retired Boston Police officer, pleaded guilty to selling a load of Stephen's stolen jewelery for $40,000.

The major witness against Flemmi was William St. Croix, formerly known as William Hussey, Stephen's illegitimate son born to his common-law wife Marion Hussey. St. Croix had turned against his father after learning that Flemmi and Bulger had strangled his half-sister, Deborah Hussey. In October 2003, Flemmi pleaded guilty in U.S. District Court in Boston to 10 counts of murder. He made the decision as a part of a deal to reduce the sentence for his brother, Michael Flemmi.

In November, Flemmi's friend Frank Salemme led police to the Hopkinton's Sportsmen's Club in Hopkinton, Massachusetts, where he said he and Flemmi had buried the bodies of Wimpy and Walter Bennett in 1967. After days of digging, the police abandoned the search, claiming that the topography of the area had been changed by the dumping of millions of tons of dirt from the Big Dig, the $15 billion public works project in downtown Boston.

On the same day that Kevin O'Neil and Kevin Weeks were arrested in Boston, Flemmi pleaded guilty in Tulsa, Oklahoma state court to the 1981 murder of business tycoon Roger Wheeler.

In April 2005, Flemmi was deposed in New York City by a group of lawyers representing the families of his and Bulger's victims, who are currently suing the federal government. Among other things, he testified that he and Bulger had been paying off six FBI agents in the Boston office. Those who could be reached issued denials. Flemmi also named Patrick Nee as the other gunman, along with Bulger, in the 1982 murders of informant Edward Brian Halloran and his friend Michael Donahue. Nee responded to The Boston Globe by calling Flemmi a "punk" and saying that "He should do his time like the rest of us." He was also questioned at length about the 1985 murder of his stepdaughter, Deborah Hussey, but declined to comment from the advice of his lawyer.

Flemmi, 79, pleaded guilty, in 2003, to 10 murders and is now serving a life sentence. According to the Federal Bureau of Prisons, he is in federal custody as of 2013 and his release date is unknown.

In popular culture

Flemmi is the basis of Frank Costello's chief enforcer and contract killer "Arnold French" portrayed by Ray Winstone in the 2006 crime thriller The Departed. The character reenacts the murder of his stepdaughter Deborah Hussey, although in the film the character based on Deborah Hussey is said to be his wife. It shows a brief scene where he garrotes his character wife, the same way he murdered his stepdaughter.

Murder victims

  • James Sousa
  • Edward G. Connors
  • Tommy King
  • Richard Castucci
  • Roger Wheeler
  • Debra Davis
  • John Callahan
  • Arthur Barrett
  • Deborah Hussey
  • John McIntyre
  • Edward Bennett
  • Walter Bennett
  • William Bennett
  • Richard Gasso
  • Stephen Hughes Jr.
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