Stephen Flemmi

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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 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[edit]

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.[citation needed]

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.[1] He was awarded the Silver Star and Bronze Star medals for valor. [2]

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 as a Roman Catholic, but unofficially converted to a Jehovah's Witness while incarcerated in 1981.[citation needed]

Criminal career[edit]

After the end of the Korean War, Flemmi and his brother Vincent joined the crew of Portuguese-American mobster Joe Barboza. Barboza had close ties to both the Patriarca crime family of Providence, Rhode Island and the Irish/Italian-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.[citation needed]

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[edit]

FBI surveillance photograph of Flemmi (left) with Winter Hill Gang boss, James Bulger (right), probably in the 1980s

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.[3]

Disgraced former 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.

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.[3]

However, Flemmi and Bulger were quickly able to turn their informant status to their own advantage. 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 United States 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. 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 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.

Taking down La Cosa Nostra their own way[edit]

Although Bulger had some dealings with Gennaro "Jerry" 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[edit]

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[edit]

In 1979 Flemmi's mother Mary was mugged in Mattapan, Massachusetts by a gang, 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.[citation needed] He felt the need to relocate 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[edit]

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.[4] 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.[5]

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,

Relationship with the FBI[edit]

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."[7] According to Weeks,

Arrest and imprisonment[edit]

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,

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.[10]

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.

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.

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.

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 November, Flemmi's friend 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 a 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. In 2008, Flemmi was one of the star witnesses when Connolly was tried for the murder of John Callahan.

According to the Federal Bureau of Prisons, he is not in federal custody as of 2013 and his release date is unknown. It has been suggested that Flemmi is in the Federal Witness Protection Program, although he is incarcerated. He is believed to have been given a false name, false criminal history.

In popular culture[edit]

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.

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

Murder victims[edit]

Other victims[edit]

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.[11]

See also[edit]


  1. ^ Hassett, George (May 13, 2013). "The FBI in Boston: Hoover, Lies and Murder". Crime Magazine. Retrieved August 17, 2015. 
  2. ^ "Stephen “The Rifleman” Flemmi". Project Marino. 
  3. ^ a b "Witness in Bulger case says reputed mob boss stuck shotgun in his mouth". Fox News. 
  4. ^ "Whitey Bulger’s Women: Inside the Terror and Glamor of His Ex-Girlfriends". The Daily Beast. 
  5. ^ Deborah Feyerick, CNN (25 July 2013). "Bulger pal on his cooperation with U.S.: 'I was dead either way' -". CNN. 
  6. ^ Kevin Weeks, Brutal, 2006, pp. 122–123.
  7. ^ Kevin Weeks, Brutal, 2006, p. 247.
  8. ^ Kevin Weeks, Brutal, 2006, p. 248.
  9. ^ Kevin Weeks, Brutal, 2006, p. 215.
  10. ^ Lehr; O'Neill 2001, p. 288-289, 291-293.
  11. ^ Wells, Jack (April 9, 2001). "Stolen Innocence: Special Report". The Boston Herald. Retrieved 20 December 2014. 
  • Lehr, Dick and O'Neill, Gerard. Black Mass: The Irish Mob, the FBI, and a Devil's Deal. New York: PublicAffairs, 2000. ISBN 1-891620-40-1.
  • Deadly Alliance: The FBI's Secret Partnership with the Mob by Ralph Ranalli
  • The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century by Howie Carr
  • Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice by Kevin Cullen and Shelley Murphy

Further reading[edit]

  • Deadly Alliance: The FBI's Secret Partnership with the Mob by Ralph Ranalli
  • 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.
  • Rifleman: The Untold Story Of Stevie Flemmi, Whitey Bulger's Partner by Howie Carr
  • Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice by Kevin Cullen and Shelley Murphy

External links[edit]