Stephen Joseph Flemmi (born June 9, 1934) is an American
gangster
A gangster (informally gangsta) is a criminal who is a member of a gang. Most gangs are considered to be part of organized crime. Gangsters are also called mobsters, a term derived from ''Organized crime, mob'' and the suffix ''wikt:-ster, -st ...
and convicted murderer and was a close associate of
Winter Hill Gang
The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts area. It was generally considered an Irish mob organization, with most gang members and the leadership consisting predominantly of ...
boss
Whitey Bulger. Beginning in 1975, Flemmi was a top echelon informant for the
Federal Bureau of Investigation
The Federal Bureau of Investigation (FBI) is the domestic Intelligence agency, intelligence and Security agency, security service of the United States and Federal law enforcement in the United States, its principal federal law enforcement ag ...
(FBI).
Despite delivering a great deal of intelligence about the inner workings of the
Patriarca crime family
The Patriarca crime family (, ), also known as the New England Mafia, the Boston Mafia, the Providence Mafia, the Boston–Providence Mafia, , Flemmi's own criminal activities proved a public relations nightmare for the FBI. He was ultimately brought up on charges under the
Racketeer Influenced and Corrupt Organizations Act
The Racketeer Influenced and Corrupt Organizations (RICO) Act is a United States federal law that provides for extended criminal penalties and a civil cause of action for acts performed as part of an ongoing criminal organization.
RICO was e ...
, and pleaded guilty in return for a sentence of life in prison.
Early life
Stephen Joseph Flemmi was the eldest of three sons (the two brothers were
Michael Flemmi and
Vincent Flemmi) born to
Italian American
Italian Americans () are Americans who have full or partial Italians, Italian ancestry. The largest concentrations of Italian Americans are in the urban Northeastern United States, Northeast and industrial Midwestern United States, Midwestern ...
parents Giovanni "John" Flemmi (1892–1991), an immigrant from
Bari
Bari ( ; ; ; ) is the capital city of the Metropolitan City of Bari and of the Apulia Regions of Italy, region, on the Adriatic Sea in southern Italy. It is the first most important economic centre of mainland Southern Italy. It is a port and ...
,
Apulia
Apulia ( ), also known by its Italian language, Italian name Puglia (), is a Regions of Italy, region of Italy, located in the Southern Italy, southern peninsular section of the country, bordering the Adriatic Sea to the east, the Strait of Ot ...
, and Mary Irene (née Misserville) Flemmi (1912–2000), who was born in
Massachusetts
Massachusetts ( ; ), officially the Commonwealth of Massachusetts, is a U.S. state, state in the New England region of the Northeastern United States. It borders the Atlantic Ocean and the Gulf of Maine to its east, Connecticut and Rhode ...
to a family from
Ceccano,
Lazio
Lazio ( , ; ) or Latium ( , ; from Latium, the original Latin name, ) is one of the 20 Regions of Italy, administrative regions of Italy. Situated in the Central Italy, central peninsular section of the country, it has 5,714,882 inhabitants an ...
. He was raised in the Orchard Park tenement located at 25 Ambrose Street in the
Roxbury neighborhood of
Boston
Boston is the capital and most populous city in the Commonwealth (U.S. state), Commonwealth of Massachusetts in the United States. The city serves as the cultural and Financial centre, financial center of New England, a region of the Northeas ...
, Massachusetts.
[Murphy, Shelley (July 20, 1998)]
"Sidekick's double-dealing career worthy of master spy"
''The Boston Globe
''The Boston Globe,'' also known locally as ''the Globe'', is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes. ''The Boston Globe'' is the oldest and largest daily new ...
''. His father was a bricklayer and veteran of the
Royal Italian Army
The Royal Italian Army () (RE) was the land force of the Kingdom of Italy, established with the proclamation of the Kingdom of Italy. During the 19th century Italy started to unify into one country, and in 1861 Manfredo Fanti signed a decree c ...
during
World War I
World War I or the First World War (28 July 1914 – 11 November 1918), also known as the Great War, was a World war, global conflict between two coalitions: the Allies of World War I, Allies (or Entente) and the Central Powers. Fighting to ...
, and his mother was a full-time homemaker.
[
Flemmi was first arrested at the age of 15 on a charge of "carnal abuse", and he later served time in a juvenile detention facility for assault.] He 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. Flemmi was awarded the Silver Star
The Silver Star Medal (SSM) is the United States Armed Forces' third-highest military decoration for valor in combat. The Silver Star Medal is awarded primarily to members of the United States Armed Forces for gallantry in action against a ...
and Bronze Star Medal
The Bronze Star Medal (BSM) is a Awards and decorations of the United States Armed Forces, United States Armed Forces decoration awarded to members of the United States Armed Forces for either heroic achievement, heroic service, meritorious a ...
decorations for valor and honorably discharged in 1955.
Criminal career
After leaving the military, Steve "The Rifleman" Flemmi, along with his brother Vincent, joined the Roxbury Gang in the late 1950s. The gang was led by the brothers Walter, William and Edward "Wimpy" Bennett and controlled bookmaking and drug dealing in the Roxbury and South End neighborhoods of Boston.[Connolly, Matt (May 22, 2023)]
"Murders by Wimpy Bennett's Roxbury Gang"
''Medium''. A soft-spoken and slender man of around 5-feet-8 and 140 pounds, Flemmi operated out of the Marconi Club, a combination bookmaker's, massage parlor and brothel, in Roxbury. Although he had a reputation as a ruthless killer, Flemmi was a popular man who was fond of nightlife, cars and the company of young women.
Flemmi, along with his mentors Walter and "Wimpy" Bennett, became a confidential informant
An informant (also called an informer or, as a slang term, a "snitch", "rat", "canary", "stool pigeon", "stoolie", "tout" or "grass", among other terms) is a person who provides privileged information, or (usually damaging) information inten ...
for the Boston Police Department
The Boston Police Department (BPD) is the primary law enforcement agency of Boston, Massachusetts, United States. Founded in 1854, the BPD is the oldest municipal police department in the United States. It is also the 20th largest law enforce ...
detective William Stuart, who offered protection to the gangsters in exchange for information on their criminal rivals. In September 1964, Stuart saved the lives of Stephen Flemmi and his brother Vincent by intervening at gunpoint to stop the hoodlum William McCarthy from gunning down the pair. McCarthy had sought revenge on the Flemmi brothers after Vincent Flemmi had killed his associate, Leo Lowry.[The George Hamilton Cold Case: How to Get Away With Murder](_blank)
Carly Carioli, ''Boston
Boston is the capital and most populous city in the Commonwealth (U.S. state), Commonwealth of Massachusetts in the United States. The city serves as the cultural and Financial centre, financial center of New England, a region of the Northeas ...
'' (February 11, 2024)
During the 1960s, gang warfare erupted in Boston and across New England
New England is a region consisting of six states in the Northeastern United States: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. It is bordered by the state of New York (state), New York to the west and by the ...
, with Irish and Italian gangsters battling over control of lucrative criminal rackets.[Mob and FBI have violent history](_blank)
David D. Haskell, United Press International
United Press International (UPI) is an American international news agency whose newswires, photo, news film, and audio services provided news material to thousands of newspapers, magazines, radio and television stations for most of the 20th ce ...
(May 4, 2001) The fiercest fighting involved two rival Irish mob groups, the Winter Hill Gang
The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts area. It was generally considered an Irish mob organization, with most gang members and the leadership consisting predominantly of ...
and the Charlestown Mob. Flemmi and his friends Joseph "the Animal" Barboza and Francis "Cadillac Frank" Salemme were recruited by the Winter Hill Gang and fulfilled a string of lucrative murder contracts during the gang wars. In addition to his links with Irish gangsters in Somerville, Flemmi associated with the Italian Mafia
"Mafia", as an informal or general term, is often used to describe criminal organizations that bear a strong similarity to the Sicilian Mafia, original Mafia in Sicily, to the Italian-American Mafia, or to other Organized crime in Italy, organiz ...
. Flemmi formed a partnership with his childhood friend Salemme, and the duo became enforcers, bookmakers and loan sharks for the Patriarca crime family
The Patriarca crime family (, ), also known as the New England Mafia, the Boston Mafia, the Providence Mafia, the Boston–Providence Mafia, in Boston's North End.
Flemmi was recruited as an informant for the Federal Bureau of Investigation
The Federal Bureau of Investigation (FBI) is the domestic Intelligence agency, intelligence and Security agency, security service of the United States and Federal law enforcement in the United States, its principal federal law enforcement ag ...
(FBI) in the mid-1960s, adopting the code name "Jack from South Boston". The FBI later referred to Flemmi as "Shogun". By the fall of 1965, Flemmi was being supervised by the FBI agent H. Paul Rico. Rico had cultivated Flemmi as an informant due to his association with the Patriarca family. Because of Flemmi's ability to provide information on the family's leadership, Rico had him designated a Top Echelon informant, the highest status an FBI source can achieve. Due to the shifting alliances and ongoing killings during the gang wars, Flemmi's life was constantly under threat, and he relied on Rico to alert him to any threats he may have learned from other informants. Because of Flemmi's usefulness as an informant, Rico overlooked Flemmi's criminal activities. By the late 1960s, Flemmi was a suspect in several murders, but the FBI chose not to question him about the killings.
Rico leaked information to members of the Winter Hill Gang which allowed them to track down and kill rival gangsters.[Former mob boss tells of access to FBI](_blank)
Shelley Murphy, ''The Boston Globe
''The Boston Globe,'' also known locally as ''the Globe'', is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes. ''The Boston Globe'' is the oldest and largest daily new ...
'' (February 13, 2004) Rico had been offended when he heard the Charlestown gangster Edward "Punchy" McLaughlin refer to Rico and his boss, J. Edgar Hoover
John Edgar Hoover (January 1, 1895 – May 2, 1972) was an American attorney and law enforcement administrator who served as the fifth and final director of the Bureau of Investigation (BOI) and the first director of the Federal Bureau o ...
, as "fags" on an illegal wiretap
Wiretapping, also known as wire tapping or telephone tapping, is the monitoring of telephone and Internet-based conversations by a third party, often by covert means. The wire tap received its name because, historically, the monitoring connecti ...
, and, in retaliation, alerted McLaughlin's rivals of his location.[ Carr, Howie (July 26, 2009)]
"Rifleman's 'Fifth' toll rises"
''Boston Herald
The ''Boston Herald'' is an American conservative daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarde ...
''. Flemmi and Salemme first attempted to murder McLaughlin when they shotgunned him in the parking lot of Beth Israel Hospital while disguised rabbi
A rabbi (; ) is a spiritual leader or religious teacher in Judaism. One becomes a rabbi by being ordained by another rabbi—known as ''semikha''—following a course of study of Jewish history and texts such as the Talmud. The basic form of t ...
s. McLaughlin had his jaw blown off but survived. On the second attempt, Flemmi and Salemme fired upon McLaughlin with machine guns during an ambush as he arrived at a girlfriend's house in Weston
Weston may refer to:
Places Australia
* Weston, Australian Capital Territory, a suburb of Canberra
* Weston, New South Wales
* Weston Creek, a residential district of Canberra
* Weston Park, Canberra, a park
Canada
* Weston, Nova Scotia
* W ...
. Although the pair missed their target, Howard "Howie" Winter shot McLaughlin's hand off with a scoped .308 Winchester rifle before he fled. McLaughlin was finally killed by two gunmen on a bus in West Roxbury
West Roxbury is a neighborhood in Boston, Massachusetts, United States, bordered by Roslindale and Jamaica Plain to the northeast, the village of Chestnut Hill and the town of Brookline to the north, the city of Newton to the northwest, t ...
on October 20, 1965. Flemmi and Salemme were alleged to be the two shooters.[Emily McIntyre and Christopher McIntyre v. the United States](_blank)
Casetext (September 5, 2006)
Although Flemmi's first gangland boss, "Wimpy" Bennett, had vowed to remain neutral in a feud between the Patriarca family and an East Boston
East Boston, nicknamed Eastie, is a Neighborhoods in Boston, neighborhood of Boston, Massachusetts, United States, which was annexed by the city of Boston in 1836. Neighboring communities include Winthrop, Massachusetts, Winthrop, Revere, Mas ...
crew headed by Barboza,[‘Rifleman’: Flemmi thought about killing his pal Whitey](_blank)
Howie Carr, ''Boston Herald
The ''Boston Herald'' is an American conservative daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarde ...
'' (April 8, 2013) a rivalry persisted between Bennett and Ilario "Larry" Zannino, Flemmi and Salemme's closest contact in the Mafia.[United States of America v. Francis P. Salemme](_blank)
Casetext (December 23, 1999) Flemmi and Salemme shot and killed the brothers "Wimpy" and Walter Bennett in succession.[Asked to identify mob boss, witness says: 'I can't see him'](_blank)
Brian Amaral, ''The Providence Journal
''The Providence Journal'', colloquially known as the ''ProJo'', is a daily newspaper serving the metropolitan area of Providence, the largest newspaper in Rhode Island, US. The newspaper was first published in 1829. The newspaper had won four ...
'' (June 6, 2018) At the behest of Zannino, 47-year-old "Wimpy" Bennett was murdered in a garage owned by Salemme on January 19, 1967.[Carr, Howie (March 2, 2008)]
"Mobster of the Week: Peter Poulos"
''Boston Herald
The ''Boston Herald'' is an American conservative daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarde ...
''. After Bennett disappeared, Flemmi notified his FBI handler Rico that there was "absolutely no chance" that he would be found alive. 55-year-old Walter Bennett then went missing on April 3, 1967 after he had been deemed a threat to Flemmi. Both men were buried at a remote location in Hopkinton.
When the third Bennett brother, William "Billy" Bennett, "began vocalizing his belief that Flemmi had murdered both his brothers", Flemmi "reluctantly decided" that he too must be killed. 56-year-old Billy Bennett was dumped from a moving car and found dead against a snowbank in the Mattapan neighborhood of Boston on December 22, 1967 after getting into a vehicle with Richard Grasso, an associate from South Boston
South Boston (colloquially known as Southie) is a densely populated neighborhood of Boston, Massachusetts, United States, located south and east of the Fort Point Channel and abutting Dorchester Bay (Boston Harbor), Dorchester Bay. It has under ...
. Stuart assisted Flemmi in post-killing cleaning after Bennett's murder. A week later, Grasso was shot twice in the head and left in the trunk of his 1967 Buick Wildcat in Brookline. Grasso was killed by Flemmi after he had "panicked" because his car was used in Billy Bennett's murder. After the killings of the Bennett brothers, Flemmi assumed control of the Roxbury Gang.
In the summer of 1967, Zannino and Peter Limone decided to sponsor Flemmi and Salemme for membership in the Patriarca family. Although prospective members would ordinarily be required to carry out a murder in order to be inducted into the Mafia, the family offered to waive the requirement due to Flemmi and Salemme's reputation as seasoned killers. In the winter of 1967, Flemmi was summoned to Providence, Rhode Island
Providence () is the List of capitals in the United States, capital and List of municipalities in Rhode Island, most populous city of the U.S. state of Rhode Island. The county seat of Providence County, Rhode Island, Providence County, it is o ...
to meet with Patriarca family boss Raymond Patriarca. Unlike Salemme, Flemmi ultimately resisted the family's attempts to recruit him as he did not trust the Mafia and felt he had sufficient protection as an FBI informant.
Flemmi was instrumental in Rico's efforts to develop Barboza into a cooperating witness for the government against the Patriarca family. After Barboza turned state's evidence, Raymond Patriarca ordered the murders of potential witnesses who might corroborate Barboza's testimony as well as Barboza's attorney, John E. Fitzgerald. On January 30, 1968, Flemmi and Salemme planted a car bomb
A car bomb, bus bomb, van bomb, lorry bomb, or truck bomb, also known as a vehicle-borne improvised explosive device (VBIED), is an improvised explosive device designed to be detonated in an automobile or other vehicles.
Car bombs can be roug ...
under the hood of Fitzgerald's Cadillac
Cadillac Motor Car Division, or simply Cadillac (), is the luxury vehicle division (business), division of the American automobile manufacturer General Motors (GM). Its major markets are the United States, Canada and China; Cadillac models are ...
automobile in Everett. Fitzgerald survived but lost his lower right leg in the explosion. According to Rico, in May 1968, Flemmi killed and buried Thomas Timmons, who had been involved in a dispute with the Patrarca family.
In September 1969, Flemmi was indicted by clandestine grand juries in two Massachusetts counties. He was charged in Suffolk County with the murder of William Bennett, and, along with Salemme, in Middlesex County with the attempted murder of Fitzgerald. After Flemmi was tipped off by Rico about the imminent indictments, he, Salemme and Peter Poulos, an associate of "Wimpy" Bennett in the South End who had witnessed Bennett's murder and assisted in the Fitzgerald bombing, fled Boston for the West Coast. After the trio made their way to Los Angeles
Los Angeles, often referred to by its initials L.A., is the List of municipalities in California, most populous city in the U.S. state of California, and the commercial, Financial District, Los Angeles, financial, and Culture of Los Angeles, ...
, Salemme left to go into hiding on his own.[Former Mob Enforcer Recounts Murders At Boss Frank Salemme's Request](_blank)
Isiah Thompson, WGBH Educational Foundation
The WGBH Educational Foundation, doing business as GBH since August 2020, is an American public broadcasting group based in Boston, Massachusetts. Established in 1951, it holds the licenses to all of the PBS member stations in Massachusetts, a ...
(June 6, 2018) While driving across the country with Poulos, Flemmi shot and killed his associate outside Las Vegas
Las Vegas, colloquially referred to as Vegas, is the most populous city in the U.S. state of Nevada and the county seat of Clark County. The Las Vegas Valley metropolitan area is the largest within the greater Mojave Desert, and second-l ...
because he and Salemme "felt ouloswouldn’t be able to stand up to pressure in court". Poulos' body was found in the Nevada desert in late 1969.
Flemmi spent four-and-a-half years as a fugitive, firstly in New York City
New York, often called New York City (NYC), is the most populous city in the United States, located at the southern tip of New York State on one of the world's largest natural harbors. The city comprises five boroughs, each coextensive w ...
and then in Montreal
Montreal is the List of towns in Quebec, largest city in the Provinces and territories of Canada, province of Quebec, the List of the largest municipalities in Canada by population, second-largest in Canada, and the List of North American cit ...
, where he worked as a printer at a newspaper. During his time on the run, Flemmi remained in contact with Rico, who kept him informed on the status of the cases against him. Rico also kept Flemmi's whereabouts confidential from Massachusetts authorities who were hunting him. After separating from Salemme because of a series of disagreements, Flemmi alerted the FBI to Salemme's location. As a result, Salemme was captured and sentenced to fifteen years in prison for the Fitzgerald bombing. The charges against Flemmi were ultimately dropped after key witnesses recanted their testimony, and Flemmi returned to Boston in May 1974.
Relationship with James J. Bulger and the FBI
In 1965, 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 "Donnie" Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howard "Howie" Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick "Pat" Nee. Winter soon chose Bulger as his man in South Boston. At this time, the Boston FBI office tried to convince Bulger to become an informant, but he initially refused. In 1974, Bulger became partners with Flemmi as enforcers for the Winter Hill Gang.
Bulger joined Flemmi in the Top Echelon informant program in 1975 when he was recruited by the FBI agent John "Zip" Connolly.[Whitey Bulger's Trial Conspiracy: John Connolly Speaks](_blank)
T.J. English, ''Newsweek
''Newsweek'' is an American weekly news magazine based in New York City. Founded as a weekly print magazine in 1933, it was widely distributed during the 20th century and has had many notable editors-in-chief. It is currently co-owned by Dev P ...
'' (June 18, 2012) [Assets and Liabilities](_blank)
Patrick Radden Keefe, ''The New Yorker
''The New Yorker'' is an American magazine featuring journalism, commentary, criticism, essays, fiction, satire, cartoons, and poetry. It was founded on February 21, 1925, by Harold Ross and his wife Jane Grant, a reporter for ''The New York T ...
'' (September 14, 2015) 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. The mobster 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.[
Rico, Flemmi's initial handler, was transferred to the ]Miami
Miami is a East Coast of the United States, coastal city in the U.S. state of Florida and the county seat of Miami-Dade County, Florida, Miami-Dade County in South Florida. It is the core of the Miami metropolitan area, which, with a populat ...
office of the FBI in 1970 and retired in 1975.[Detective dents Rico case after decades of pursuit](_blank)
Kelly Kurt, '' The Standard-Times'' (October 20, 2003) [The Paul Rico Case](_blank)
''FBI Studies'' (June 14, 2016) With assistance from Bulger, Connolly revived Flemmi's relationship with the FBI. Connolly served as the handler of Flemmi and Bulger from 1975 until his retirement in 1990. United by a shared an antipathy for the Patriarca family, a desire to profit from its destruction, and the protection of the FBI, Flemmi and Bulger forged a formidable and enduring partnership. As the alliance between the gangsters and the FBI developed, Flemmi and Bulger dined periodically with FBI agents investigating the Mafia, including Connolly and several of his colleagues on the Boston Organized Crime squad, Connolly's supervisors, John Morris and James Ring, and Joseph D. Pistone, who had went undercover to infiltrate the Bonanno crime family in New York as "Donnie Brasco".
In 1997, shortly after ''The Boston Globe
''The Boston Globe,'' also known locally as ''the Globe'', is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes. ''The Boston Globe'' is the oldest and largest daily new ...
'' 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,
Flemmi and Bulger assisted the FBI in planting a covert listening device
A covert listening device, more commonly known as a bug or a wire, is usually a combination of a miniature radio transmitter with a microphone. The use of bugs, called bugging, or wiretapping is a common technique in surveillance, espionage and ...
in the headquarters of Patriarca family underboss
Underboss () is a position within the leadership structure of certain organized crime groups, particularly in Sicilian Mafia, Sicilian and Italian-American Mafia crime families. The underboss is second in command to the Crime boss, boss. The un ...
Gennaro "Jerry" Angiulo at 98 Prince Street in the North End. At Morris' request, the duo visited the location in November 1980 and Flemmi subsequently produced a drawn diagram of Angiulo's office, which let FBI agents know exactly where to place bugs.[Agents gave Bulger starring role - but was it real?](_blank)
Gerard O'Neill, ''The Boston Globe
''The Boston Globe,'' also known locally as ''the Globe'', is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes. ''The Boston Globe'' is the oldest and largest daily new ...
'' (June 11, 2014) Although Flemmi was concerned that information gathered on the wiretap may implicate him and Bulger in criminal activity, the FBI assured him that nothing on the tapes would be used against them.[United States of America v. Stephen J. Flemmi](_blank)
FindLaw
FindLaw is a business of Internet Brands that provides online legal information in the form of state laws, case law and codes, legal blogs and articles, a lawyer directory, DIY legal services and products, and other legal resources. The compa ...
(September 11, 2000)
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 and Michelle Davis, and Deborah Hussey. According to Salemme: "There's two things with Flemmi paramount to everything – his money and his women, not necessarily in that order".[Howie Carr: Final look at Salemme’s history before sentencing](_blank)
Howie Carr, ''Boston Herald
The ''Boston Herald'' is an American conservative daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarde ...
'' (June 24, 2018)
Flemmi met Debra Davis at a jewelry store after his return to Boston in 1974, and the couple dated for more than seven years. They lived together at an apartment in Randolph, along with Davis' sister, Michelle.[Family of mobster’s murdered girlfriend awarded $33.5 million – but gangsters are unlikely to pay](_blank)
John P. Kelly, ''The Patriot Ledger
''The Patriot Ledger'' is a daily newspaper in Quincy, Massachusetts, that serves the South Shore. It publishes Monday through Saturday.
History
The paper was founded on , as the weekly ''Quincy Patriot'' by John Adams Green and Edmund Butl ...
'' (September 18, 2009) Flemmi and Davis' relationship became strained after Flemmi began sexually abusing 14-year-old Michelle Davis. During an argument at the Bay Tower Room restaurant at 60 State Street, Flemmi, in frustration, tacitly admitted to her that he and Bulger were FBI informants. An enraged Bulger then allegedly insisted that Davis be killed, to which Flemmi acquiesced. On September 17, 1981, 26-year-old Davis was strangled to death in the basement of Flemmi's mother's home in South Boston. Flemmi claimed that Davis was murdered by Bulger. According to John Martorano, Flemmi admitted that he had "accidentally" strangled her himself. Flemmi pulled out Davis' teeth and cut off her hands to complicate identifying the body, and she was buried at Tenean Beach on the Neponset River
The Neponset River is a river in eastern Massachusetts in the United States. Its headwaters are at the Neponset Reservoir in Foxborough, near Gillette Stadium. From there, the Neponset meanders generally northeast for about to its mouth at ...
in North Quincy. As he and Bulger buried the body, Flemmi claimed to have considered killing Bulger for the murder. Flemmi misled Davis' mother Olga into thinking her daughter had moved to Texas. Wracked with shame and guilt over the abuse she had suffered at the hands of Flemmi, Michelle Davis fell into drug addiction and alcoholism, and died from a drug overdose in January 2006.
Four years after killing Davis, in 1985, Flemmi and Bulger killed Deborah Hussey, who was also Flemmi's stepdaughter (born to his common-law wife, Marion A. Hussey). Deborah was first sexually molested by Flemmi in her teens—she informed her mother that Flemmi had molested her for years—and had been his girlfriend since. In the days prior to her murder, Hussey was close to breaking up with Flemmi and telling her mother about their relationship, which is thought to have been the motive for her murder.
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 Frank Salemme
Flemmi's longtime partner Salemme was released from state prison in 1988 after serving fifteen years for the attempted murder of Fitzgerald,[Frank Salemme, One-Time Head of the New England Mafia, Dies at 89](_blank)
Clay Risen, ''The New York Times
''The New York Times'' (''NYT'') is an American daily newspaper based in New York City. ''The New York Times'' covers domestic, national, and international news, and publishes opinion pieces, investigative reports, and reviews. As one of ...
'' (December 21, 2022) and was subsequently inducted as a " made" member of the Patriarca family.[‘Cadillac Frank’ Salemme obituary](_blank)
''The Times
''The Times'' is a British Newspaper#Daily, daily Newspaper#National, national newspaper based in London. It began in 1785 under the title ''The Daily Universal Register'', adopting its modern name on 1 January 1788. ''The Times'' and its si ...
'' (December 29, 2022) To the disillusionment of Bulger, Flemmi drifted closer to Salemme and the Patriarca family as Salemme attempted to recruit him into the Mafia. Using his contacts with Connolly, Bulger plotted to have Salemme eliminated by his own crime family. Connolly had a story planted in a newspaper falsely stating that Salemme was planning to eradicate the East Boston
East Boston, nicknamed Eastie, is a Neighborhoods in Boston, neighborhood of Boston, Massachusetts, United States, which was annexed by the city of Boston in 1836. Neighboring communities include Winthrop, Massachusetts, Winthrop, Revere, Mas ...
faction of the Patriarca family. On June 16, 1989, Salemme survived a murder attempt when he was shot by East Boston mobsters outside a pancake house in Saugus.
By 1991, Salemme was the ''de facto'' leader of the Mafia in New England. To assure his position as the head of the Patriarca family, Salemme built an alliance between the Mafia and the Winter Hill Gang, effectively uniting Boston's Italian and Irish crime groups.[Reputed Mafia leader arrested after 2 years](_blank)
''Tampa Bay Times
The ''Tampa Bay Times'', called the ''St. Petersburg Times'' until 2011, is an American newspaper published in St. Petersburg, Florida, United States. It is published by the Times Publishing Company, which is owned by The Poynter Institute ...
'' (August 13, 1995) Flemmi and an associate, George Kaufman, served as the liaisons between the Winter Hill Gang and the Patriarca family.[Feds indict alleged New England mob bosses](_blank)
United Press International
United Press International (UPI) is an American international news agency whose newswires, photo, news film, and audio services provided news material to thousands of newspapers, magazines, radio and television stations for most of the 20th ce ...
(January 10, 1995) Nonetheless, Bulger and Connolly's plan to sow discontent in the Patriarca family to prevent the Mafia from usurping the Winter Hill Gang as Boston's preemeninent organized crime force succeeded as the Patriarca family descended into a state of internal warfare following the shooting of Salemme.
According to Flemmi, he witnessed the murder of nightclub owner Steven DiSarro when he happened to visit Salemme's home in Sharon
Sharon ( 'plain'), also spelled Saron, is a given name as well as a Hebrew name.
In Anglosphere, English-speaking areas, Sharon is now predominantly a feminine given name, but historically it was also used as a masculine given name. In Israel, ...
on May 10, 1993, walking in on Salemme's son, Francis "Frankie Boy" Salemme Jr., strangling DiSarro as an associate, Paul Weadick, held his legs and Salemme Sr. looked on.['Pure evil': Ex-New England mob boss gets life in prison for 1993 murder](_blank)
Nate Raymond, Reuters
Reuters ( ) is a news agency owned by Thomson Reuters. It employs around 2,500 journalists and 600 photojournalists in about 200 locations worldwide writing in 16 languages. Reuters is one of the largest news agencies in the world.
The agency ...
(September 14, 2018) Salemme had ordered DiSarro's murder over fears he may cooperate with a federal investigation into illegal activities at the Channel nightclub in South Boston, in which Salemme and his son held a financial interest.[Former Mafia Boss and Associate Convicted of 1993 Murder](_blank)
United States Department of Justice
The United States Department of Justice (DOJ), also known as the Justice Department, is a United States federal executive departments, federal executive department of the U.S. government that oversees the domestic enforcement of Law of the Unite ...
(June 22, 2018) DiSarro was buried behind a mill in Providence, Rhode Island
Providence () is the List of capitals in the United States, capital and List of municipalities in Rhode Island, most populous city of the U.S. state of Rhode Island. The county seat of Providence County, Rhode Island, Providence County, it is o ...
.
In April 1994, a joint task force of the Drug Enforcement Administration
The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...
(DEA), the Massachusetts State Police, and the Boston Police Department
The Boston Police Department (BPD) is the primary law enforcement agency of Boston, Massachusetts, United States. Founded in 1854, the BPD is the oldest municipal police department in the United States. It is also the 20th largest law enforce ...
launched an investigation into gambling operations in which the Winter Hill Gang and the Patriarca family collaborated.[Photos: Who's Who in the Bulger Case](_blank)
WCVB-TV
WCVB-TV (channel 5) is a television station in Boston, Massachusetts, United States, affiliated with ABC and owned by Hearst Television. The station's studios are located on TV Place (off Gould Street near the I-95/ MA 128/Highland Avenue in ...
(June 25, 2011)
Arrest and imprisonment
By the end of 1994, the Massachusetts State Police and the U.S. Attorney's Office had amassed enough evidence to indict Flemmi, Bulger and Salemme on 35 counts of racketeering and extortion.[Galway native set to testify against Bulger in murder trial](_blank)
Pierce O’Reilly, '' The Irish Echo'' (February 16, 2011) In December 1994, Connolly informed Bulger and Flemmi that several imprisoned Jewish-American bookmakers had agreed to testify to paying them protection money
A protection racket is a type of racket and a scheme of organized crime perpetrated by a potentially hazardous organized crime group that generally guarantees protection outside the sanction of the law to another entity or individual from viol ...
. As a result, sealed indictments had come from the Department of Justice
A justice ministry, ministry of justice, or department of justice, is a ministry or other government agency in charge of the administration of justice. The ministry or department is often headed by a minister of justice (minister for justice in a ...
, and the FBI was due to make arrests during the Christmas season.[Mobster tells of gang payoffs to FBI](_blank)
United Press International
United Press International (UPI) is an American international news agency whose newswires, photo, news film, and audio services provided news material to thousands of newspapers, magazines, radio and television stations for most of the 20th ce ...
(May 16, 2002) In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Catherine Greig.[Bulger girlfriend testifies at mob trial](_blank)
Curt Anderson, ''Telegram & Gazette
The ''Telegram & Gazette'' (and ''Sunday Telegram'') is the only daily newspaper of Worcester, Massachusetts. The paper, headquartered at 100 Front Street and known locally as ''the Telegram'' or the ''T & G'', offers coverage of all of Worceste ...
'' (October 17, 2008) Flemmi in turn warned Salemme,[Bulger’s long ties to south suburbs](_blank)
''The Boston Globe
''The Boston Globe,'' also known locally as ''the Globe'', is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes. ''The Boston Globe'' is the oldest and largest daily new ...
'' (February 12, 2012) who took flight to Providence and then West Palm Beach, Florida
West Palm Beach is a city in and the county seat of Palm Beach County, Florida, United States. It is located immediately to the west of the adjacent Palm Beach, Florida, Palm Beach, which is situated on a barrier island across the Lake Worth Lag ...
.[When The Feds Moved In, Whitey Slipped Away](_blank)
David Boeri, WBUR-FM
WBUR-FM (90.9 FM) is a public radio station located in Boston, Massachusetts, owned by Boston University. Its programming is also known as WBUR News. The station is the largest of three NPR member stations in Boston, along with WGBH and W ...
(January 5, 2010)
According to Kevin Weeks,
Flemmi, however, miscalculated how soon the arrests would take place and remained in Boston. On January 5, 1995, he was arrested by the state police as he left Schooner's Restaurant in a car along with a woman companion. A bewildered Flemmi asked agents "Is this a gag?" as he was being arrested.[Howie Carr: Happy 90th birthday to Stephen ‘The Rifleman’ Flemmi, Boston’s most prolific serial killer](_blank)
Howie Carr, ''Boston Herald
The ''Boston Herald'' is an American conservative daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarde ...
'' (June 9, 2024) He was held without bail and incarcerated at the Plymouth County House of Correction.[Flemmi's son to testify against father in court](_blank)
Martin Finucane, '' The Standard-Times'' (December 15, 2000)
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. Flemmi's problem was that, without immunity, he could not admit to killings he had not been charged with. By the time Flemmi 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 Flemmi, 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 Department
The Boston Police Department (BPD) is the primary law enforcement agency of Boston, Massachusetts, United States. Founded in 1854, the BPD is the oldest municipal police department in the United States. It is also the 20th largest law enforce ...
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 Flemmi's stolen jewelry for $40,000.
By 2003, Flemmi realized he was out of options. Salemme and several others had joined Weeks in turning informer, and had disclosed enough information to ensure Flemmi would die in prison. He also faced possible execution for murders in Florida and Oklahoma. In October, Flemmi pleaded guilty in U.S. District Court in Boston to 10 counts of murder and accepted a sentence of life in prison without parole.["Winter Hill Gang Leader Pleads Guilty"](_blank)
''Drug Enforcement Administration
The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...
''. October 14, 2003. As a part of a deal, the sentence given to his brother, Michael, was reduced.
Flemmi testified against Connolly at the latter's trial for the murder of John Callahan, the former president of World Jai Alai. Callahan had been killed in 1981 after he was implicated in the murder of his successor as president, Roger Wheeler. According to Flemmi, Connolly told him and Bulger that Callahan could potentially turn state's evidence and implicate them in Wheeler's murder. He also testified against Bulger in the latter's 2013 trial for murder and racketeering, at which Bulger was sentenced to life plus five years.
As a cooperating witness, Flemmi is held in an undisclosed penitentiary as part of the Federal Bureau of Prisons
The Federal Bureau of Prisons (BOP) is a Federal law enforcement in the United States, federal law enforcement agency of the United States Department of Justice that is responsible for all List of United States federal prisons, federal prisons ...
' Witness Security ( WitSec) program.On August 18, 2021, Flemmi was denied parole by the Florida Commission on Offender Review after seeking compassionate release
Compassionate release is a process by which inmates in criminal justice systems may be eligible for immediate early release on grounds of "particularly extraordinary or compelling circumstances which could not reasonably have been foreseen by t ...
. His next review is not scheduled until 2028, when he will be 93 years old. His parole is scheduled for May 4, 2218.
Victims
Murdered
* Arthur "Bucky" 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
Others
Stephen Flemmi and Whitey Bulger are alleged to have committed statutory rape
In common law jurisdictions, statutory rape is nonforcible sexual activity in which one of the individuals is below the age of consent (the age required to legally consent to the behaviour). Although it usually refers to adults engaging in sex ...
against 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.
Depictions in popular culture
In the Whitey Bulger biopic '' Black Mass'' (2015), Flemmi is portrayed by Rory Cochrane.
See also
* Timothy A. Connolly 3rd
References
Further reading
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External links
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{{DEFAULTSORT:Flemmi, Stephen
1934 births
Living people
20th-century American criminals
American male criminals
American gangsters of Italian descent
American people convicted of murder
American prisoners sentenced to life imprisonment
American rapists
FBI informants convicted of crimes
Gangsters from Boston
Gangsters sentenced to life imprisonment
Mafia hitmen
Military personnel from Massachusetts
Patriarca crime family
People convicted of murder under the RICO Act
People from Milton, Massachusetts
People of Apulian descent
People of Lazian descent
Police informants
Prisoners sentenced to life imprisonment by the United States federal government
Recipients of the Silver Star
United States Army personnel of the Korean War
United States Army soldiers
Winter Hill Gang
Child sexual abuse in the United States