Stephen Joseph “The Rifleman” Flemmi (born June 9, 1934) is an American gangster and close associate of Winter Hill Gang boss Whitey Bulger. Beginning in 1975, 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 Irish immigrant 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 enlisted in the Army in 1951 at the age of 17 and served two tours of duty in Korea with the 187th Airborne Regimental Combat Team. He was awarded the Silver Star and Bronze Star medals for valor.

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.

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 off 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.

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.

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, Connolly 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.

During the discovery phase, two of Flemmi’s co-defendants, Boston mafiosi Frank Salemme and Bobby DeLuca, were listening to tape from a roving bug, which is normally authorized when the FBI has no advance knowledge of where criminal activity will take place. They overheard two of the agents who were listening in on the bug mention that they should have told one of their informants to give “a list of questions” to the other wiseguys. When their lawyer, Tony Cardinale, learned about this, he realized that the FBI had lied about the basis for a roving bug in order to protect an informant. Suspecting that this was not the only occasion that this happened, Cardinale sought to force prosecutors to reveal the identities of any informants used in connection with the case.

Eventually, both Bulger and Flemmi were revealed to be FBI informants. Flemmi believed that as a result, he had protection from the FBI, but not immunity. He initially planned to prove through his own testimony and that of others that he was being prosecuted for crimes that were effectively authorized by the FBI. He believed that as a result, Judge Mark L. 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. By the time Stephen took the stand, in August 1998, John Martorano had pleaded guilty and 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.

However, by 2000, it was obvious this gambit had failed. Out of desperation, he ordered Weeks to get in touch with retired state police lieutenant Richard J. Schneiderhan, a lifelong friend who had been on Winter Hill’s payroll for virtually his entire career, to leak information about several wiretaps investigators were monitoring in hopes of tracking down Bulger. However, when Weeks reached a plea bargain a year later, he admitted Schneiderhan’s role in the leak. Schneiderhan was ultimately convicted of obstructing justice and was sentenced to 18 months in prison. In 2000, Flemmi’s brother Michael, then a retired Boston Police officer, was arrested for moving an arsenal of more than 70 weapons from their mother’s shed after learning that it was to be the target of a search warrant. He was convicted in 2002 and sentenced to 10 years in prison. A year later, he pleaded guilty to selling a load of Stephen’s stolen jewelry for $40,000.

By 2003, Flemmi knew he was at the end of his tether. Salemme, Weeks and several others had turned informer, and had disclosed enough information to send Flemmi to prison for life, and possibly send him to death. In October, 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 popular culture

Flemmi is portrayed by Rory Cochrane in the 2015 Whitey Bulger biopic Black Mass.

Murder victims

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

Other victims

Stephen Flemmi and Whitey Bulger are alleged to have statutorily raped numerous underage girls, some as young as 13, during the 1970s and 80s, deliberately getting them hooked on heroin and then sexually exploiting them for years.