Stephen Flemmi: Wikis


Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.


From Wikipedia, the free encyclopedia

Stephen "The Rifleman" Flemmi

Stephen Joseph "The Rifleman" Flemmi (born June 9, 1935) is a decorated veteran of the Korean War, as well as an Italian-American mobster and close assocatiate 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 in Federal prison.


Early years

Stephen Joseph Flemmi was the eldest of two brothers Vincent Flemmi and Michael Salvatore Flemmi born to Italian immigrants Giovanni and Mary Irene Flemmi. He was raised in the Orchard Park tenement located at 25 Ambrose Street in Roxbury, Massachusetts. This was the same neighborhood that Patriarca crime family capo Ilario Zannino was born and raised. His father Giovanni was a bricklayer and veteran of the Royal Italian Army during World War I. Stephen's mother was a full-time homemaker who never lost her Italian accent and spoke only broken English.

Stephen stands at 5'8" and weighs 150 pounds with a slender build but earned a reputation as a hardened mobster with a hair-trigger temper. Prior to imprisonment, Flemmi had a natural dark tan and curly dark hair with deep set brown eyes. He 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 as a child as a Roman Catholic but later unofficially converted to Jehovah's Witness while incarcerated in 1981.

Korean War

Flemmi enlisted in the U.S. Army at the age of seventeen, and served two tours with the 187th Infantry Regiment. He also served as a paratrooper during the Korean War and was honorably discharged in 1955. He was highly decorated, being awarded the Silver Star and Bronze Star for rescuing his fellow soldier James W. Lang in a bloody battle with the Chinese Communist Army. He later renewed his friendship with Lang after meeting him thirty-five years later at a veteran's reunion in Norfolk, Virginia.

At his friend's urging, Stephen became a prominent and popular member of the International Association of Airborne Veterans (IAAV) and travelled the world jumping out of planes with active paratroopers in South Africa, East Germany and Thailand. While a IAAV member he fraternized with military generals, sending them small gifts after returning to Boston. In 1993, he donated $3,000 to a Korean War memorial in Charlestown, Massachusetts where his name is inscribed on a granite bench reading, "In memory of the paratroopers who made the supreme sacrifice on the battlefields of Korea."

In later years, Flemmi was dubbed, "The Rifleman," by the Boston media for the sharpshooting skills he had demonstrated in combat.

Criminal career

After the end of the Korean War, Stephen and his brother Vincent Flemmi, joined the crew of Portuguese-American mobster Joe Barboza. Barboza possessed 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, MacLaughlin 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 MacLean. 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 mobbed up 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. Flemmi was considered the best kind of informant - an Italian-American who was trusted by the Mafia, but had no compunctions about betraying on them.

In 1967, after crew leader Joe Barboza became an 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 as fugitives from justice. After Salemme was arrested in New York City in 1972, Flemmi fled to Montreal, Quebec.


He would later say that his two years in Montreal were the happiest of his life. On the witness stand, he later alleged that he didn't even want to return to Boston. He said H. Paul Rico made him return. Stephen kept in tune of Frank Salemme's trial for the car bombing in the Boston papers. But the main witness against Salemme also testified that Stephen was not present at the bombing. In May 1974 Rico told him it was safe to return to Boston. Once the charges against him were dismissed, Stephen returned. He moved back with his mistress, Marion Hussey, in suburban Milton, Massachusetts.

Relationship with James J. Bulger

FBI surveillance photograph of Flemmi (left) with Winter Hill Gang boss, James Bulger (right) c. 1980s.

In 1967, James J. 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. Likely due to his talent for making money on the streets, Winter soon chose Bulger as his man in South Boston. Shortly afterwards, Bulger became partners with Flemmi.

At this time, the Boston FBI office tried to convince Bulger to become an informant, but he refused. Although he had followed Flemmi's example by 1975, how and why he did so continues to be disputed.

FBI agent John Connolly, 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 as well.

In a conversation that Flemmi fully expected to be his last, 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. 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. He has said and that Bulger was likely "caught between a rock and a hard place;" supply information to the FBI or return 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 discarded his moral compass, becoming, to all intents and purposes, 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 (FBI) 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 far more of the publicity on which the FBI's funding depends. 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.

Taking down La Cosa Nostra their own way

Bulger preferred dealing with his fellow natives of South Boston. Although Bulger had some dealings with Jerry Anguilo, 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 sought out Stephen more and more often for reliable information.

In contrast Flemmi, who was full-blooded Italian, was considered a stand-up guy by La Cosa Nostra because of his tough-guy ways and talent for making money on the street. In fact, Flemmi was actually offered the privilege of becoming a Made man, as was Johnny Martorano, another Winter Hill Gang member. However, Flemmi politely declined the offer from Anguilo and Ilario Zannino and stayed with the Winter Hill Gang.

At one point, Bulger and Flemmi took out a $200,000 loan from Anguilo. When Anguillo asked them about repayment, Bulger and Flemmi stalled him. Naturally, Anguilo was infuriated and a serious gang war looked imminent. However, Flemmi had already been describing the layout of the Anguilo'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

The second victim was John McIntyre, a thirty-two 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 Barret, McIntyre was lured to the house and killed in the basement. Bulger shot McIntyre in the back of the head with a .22 calibre rifle, killing him instantly. Weeks and Flemmi buried McIntyre's remains just like they had done with Barret.

Relationship with parents

In 1979 Stephen'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 Stephen who remained close to his ailing mother over the years. He felt the need to locate his parents to a nice, low crime neighbourhood. After consulting James J. Bulger, he was told that 832 East Third Street, next door to Bulger's brother William Bulger at 828, happened to be up for sale. Flemmi's parents' house eventually became a meeting place for James J. Bulger, Stephen, John Connolly, and H. Paul Rico to meet.

Married life

Deborah Hussey, stepdaughter of Stephen

In the 1950s, Flemmi was married an Irish-American woman named Jeanette, from whom he later became estranged. By 1980, he planned to legally divorce in 1980 and marry his longtime mistress Marilyn DeSilva, but it is unknown if he ever followed through with the legal actions. Throughout his life, Stephen was a womanizer engaged in clandestine affairs with several other women, including sisters, Debra and Michelle Davis, and Debra Hussey.

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 Hussey and Robert Hussey, and two daughters. He also became the stepfather of two daughters including Debra, 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 more of less living with her mother in Milton. By the age of seventeen, his stepdaughter had dropped out of high school and graduated from working as a waitress in Dorchester to working as a stripper and occasional prostitue in Boston's Combat Zone. By 1984, his stepdaughter was out of control, willing to say or do anything.

In response, 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 still continued to see him. She didn't know about the murder, but she knew about the sex. That didn't make any sense either."[1]

Relationship with the FBI

FBI Special Agent H. Paul Rico first recruited Stephen Flemmi as an informant in 1965. At the time Flemmi was a tough, smart, and connected, exactly the kind of man the FBI needed to obtain intelligence about the Patriarca crime family.

In 1997, shortly after the Boston Globe disclosed that Bulger and Flemmi had been informants, former Bulger confidant Kevin Weeks met with retired Agent John 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."[2] 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."[3]

Arrest and imprisonment

In December 1994, Bulger and Flemmi were informed by mobbed up FBI Agent John Connolly 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, Theresa Stanley.

According to Kevin Weeks,

"In 1993 and 1994, before the pinches came down, Jimmy and Stevie were travelling on the French and Italian Riviera. The two of them travelled 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."[4]

Flemmi, however, chose to remain in Boston and was swiftly taken into custody and incarcerated at the Plymouth County House of Correction. Stephen believed he had protection, but not immunity. But as 1995 faded into 1996, it began to dawn on Stephen that no one was going to bail him out, figuratively or literally.

With his lawyer, he planned to prove through the testimony of his self and others, that he had indeed had protection from the FBI, Judge Wolf would have no choice but to throw out the entire indictment. But 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 that $1 million during his years as a wanted fugitive between 1978 and 1995. To many questions about the murders Flemmi was involved in, he plead the Fifth Amendment.

In 1999 Mary Flemmi finally 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 (drug smuggler), Debra Davis, Brian Halloran, and both 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, Stephen Flemmi's brother Michael, then a retired Boston Police officer, plead guilty to selling a load of Stephen's stolen jewellery for $40,000.

The major witness against him was Stephen's nephew, William St. Croix, formerly known as William Hussey, Stephen's illegitimate son born to his common-law wife Marion Hussey who had been living with for nearly thirty years. St. Croix had turned against his father after learning that Flemmi and Bulger had strangled his half-sister, Deborah Hussey. In October 2003, Stephen plead guilty in U.S. District Court in Boston to ten counts of murder. He made the decision as a part of a deal to reduce the sentence for his brother Michael Flemmi, the former Boston police officer, who is not scheduled to be released from prison until 2010.

In open court, prosecutor Fred Wyshak read aloud Flemmi's agreed-upon statement, and as Wyshak reached the paragraph about the 1981 murder of his girlfriend-mistress Debra Davis, one of her brothers stood up in court and screamed at Stephen, "Fuck you, you fucking piece of shit!" In November, Stephen's friend Frank Salemme led police to the Hopkinton's Sportsmen's Club located at 95 Lumber Street in Hopkinton, Massachusetts, where he said he and Stephen 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 that was now the subject of multiple federal and state corruption investigations.

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

In April 2005, Stephen was deposed in New York City by a group of lawyers representing the families of his and Bulger's victims who are now currently suing the federal government. Among other things, Stephen 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, who happened to be in the wrong place at the wrong time. Nee responded to The Boston Globe by calling Stephen, a "punk" and 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.

In popular culture

He 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. His character "Arnold French" reenacts the murder of his stepdaughter Debra Hussey, although in the film the character based on Debrah 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


  1. ^ Kevin Weeks, Brutal, pages 122-123.
  2. ^ Kevin Weeks, Brutal, 2006, page 247.
  3. ^ Kevin Weeks, Brutal, 2006, page248.
  4. ^ Kevin Weeks, Brutal, page 215.

Further reading

  • Deadly Alliance: The FBI's Secret Partnership with the Mob by Ralph Ranalli
  • FBI, CIA, the Mob, and Treachery by Rodney Stich
  • The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century by Howie Carr
  • Brutal; My Life in Whitey Bulger's Irish Mob, by Kevin Weeks.

External links

Got something to say? Make a comment.
Your name
Your email address