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Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of
Winter Hill Gang The Winter Hill Gang is a loose confederation of organized crime figures in the Boston, Massachusetts, area. The gang members and leadership are predominantly Irish-American and Italian-American descent. The organization itself derives its ...
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 and security service of the United States and its principal federal law enforcement agency. Operating under the jurisdiction of the United States Department of Justice ...
(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, or The Office is an Italian-American American Mafia, Mafia crime family, family in New England. It has two distinct factions, one based ...
, 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 en ...
, and pleaded guilty in return for a sentence of life in prison.


Early years

Stephen Joseph Flemmi was the eldest of three sons (the two brothers were Michael Flemmi and
Vincent Flemmi Vincent James Flemmi (September 5, 1935 – October 16, 1979), also known as "Jimmy The Bear", was an American mobster who freelanced for the Winter Hill Gang and the Patriarca crime family. He was also a longtime informant for the Federal Bureau ...
) born to
Italian Italian(s) may refer to: * Anything of, from, or related to the people of Italy over the centuries ** Italians, an ethnic group or simply a citizen of the Italian Republic or Italian Kingdom ** Italian language, a Romance language *** Regional Ita ...
immigrants Giovanni Flemmi (1892–1991), and Mary Irene (née Misserville) Flemmi (1912–2000), who was of Irish descent. He was raised in the Orchard Park tenement located at 25 Ambrose Street in
Roxbury Roxbury may refer to: Places ;Canada * Roxbury, Nova Scotia * Roxbury, Prince Edward Island ;United States * Roxbury, Connecticut * Roxbury, Kansas * Roxbury, Maine * Roxbury, Boston, a municipality that was later integrated into the city of Bo ...
,
Massachusetts Massachusetts (Massachusett: ''Muhsachuweesut Massachusett_writing_systems.html" ;"title="nowiki/> məhswatʃəwiːsət.html" ;"title="Massachusett writing systems">məhswatʃəwiːsət">Massachusett writing systems">məhswatʃəwiːsət'' En ...
. His father was a bricklayer and veteran of the
Royal Italian Army The Royal Italian Army ( it, Regio Esercito, , Royal Army) 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 Manf ...
during
World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was List of wars and anthropogenic disasters by death toll, one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, ...
, 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 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 an e ...
and
Bronze Star Medal The Bronze Star Medal (BSM) is a United States Armed Forces decoration awarded to members of the United States Armed Forces for either heroic achievement, heroic service, meritorious achievement, or meritorious service in a combat zone. W ...
decorations for valor and
honorably discharged A military discharge is given when a member of the armed forces is released from their obligation to serve. Each country's military has different types of discharge. They are generally based on whether the persons completed their training and th ...
in 1955.


Relationship with James J. Bulger

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 South Boston is a densely populated neighborhood of Boston, Massachusetts, located south and east of the Fort Point Channel and abutting Dorchester Bay. South Boston, colloquially known as Southie, has undergone several demographic transformat ...
mob boss
Donald Killeen Donald Killeen (September 14, 1923 – May 13, 1972) was an American mob boss who controlled criminal activity, primarily bookmaking, loansharking, and numbers in South Boston, during the late 1940s to the early 1970s. Early life Donald Killee ...
. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss
Howie Winter Howard Thomas Winter (March 17, 1929 – November 12, 2020) was an American mobster. He was a leader of the Winter Hill Gang. Early life Winter was born in Boston, Massachusetts on March 17, 1929. He was of German and Irish descent. Winter die ...
mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by
Patrick Nee Patrick Joseph Nee (born December 22, 1944) is an Irish-American former mobster and Irish republican sympathizer. A former member of the Mullen Gang and the Winter Hill Gang, he is a Vietnam War veteran, and author of ''A Criminal and an Iri ...
. 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 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.


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. 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
garrot A garrote or garrote vil (a Spanish word; alternative spellings include garotte and similar variants'' Oxford English Dictionary'', 11th Ed: garrotte is normal British English spelling, with single r alternate. Article title is US English spelli ...
ted her. Her body was then buried in the basement. According to Kevin Weeks,


Relationship with the FBI

Rico first recruited Flemmi as an informant in 1965. In 1997, shortly after ''
The Boston Globe ''The Boston Globe'' is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes, and has a total circulation of close to 300,000 print and digital subscribers. ''The Boston Glob ...
'' disclosed that Bulger and Flemmi had been informants, former Bulger confidant Kevin Weeks met with 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." According to Weeks,


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 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 vi ...
. 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. In response, Bulger fled Boston on December 23, 1994, accompanied by his
common law wife Common-law marriage, also known as non-ceremonial marriage, marriage, informal marriage, or marriage by habit and repute, is a legal framework where a couple may be considered married without having formally registered their relation as a civi ...
, 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. 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 he couldn't really come clean. Without immunity, he couldn't admit to killings he hadn't 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), dating back to 1854, holds the primary responsibility for law enforcement and investigation within the city of Boston, Massachusetts. It is the oldest municipal police department in the United States. Th ...
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 at the end of his tether. Salemme and several others had joined Weeks in turning informer, and had disclosed enough information to ensure Flemmi would die in prison. He also potentially faced the death penalty 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. He made the decision as a part of a deal to reduce the sentence for his brother, Michael Flemmi. 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.


Depictions in popular culture

In the Whitey Bulger biopic '' Black Mass'' (2015), Flemmi is portrayed by Rory Cochrane.


Murder victims

* Arthur “Bucky” Barrett * Edward Bennett * Walter Bennett * William Bennett *
Richard Castucci Richard J. Castucci Sr. (December 1, 1928 – December 29, 1976) was an American member of the Patriarca crime family who owned several strip clubs and was involved in illegal gambling. Castucci eventually became a government informant. Early li ...
*
Edward G. Connors Edward George Connors (January 1, 1933 – June 12, 1975), also known as "The Bulldog", was an American associate of the Winter Hill Gang and successful bar owner in Savin Hill. Early life Edward George Connors was born in Sharon, Massachusetts ...
* Debra Davis * Richard Gasso * Stephen Hughes Jr. * Deborah Hussey * Tommy King * John McIntyre *
Edward McLaughlin Edward J. McLaughlin (May 16, 1917 – October 20, 1965) was an American boxer and a member of " The McLaughlin Brothers" gang of Charlestown, Massachusetts. Vincent Teresa, former mobster described Edward in his biography "My Life in the Mafia" ...
* James Sousa * Roger Wheeler


Other victims

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 behavior). Although it usually refers to adults engaging in sexual ...
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.


See also

* Timothy A. Connolly 3rd


References


Bibliography

* * * * *


External links

* * * * * * * {{DEFAULTSORT:Flemmi, Stephen 1934 births Living people United States Army personnel of the Korean War American gangsters of Italian descent American people convicted of murder American rapists Federal Bureau of Investigation informants Mafia hitmen People convicted of racketeering People from Boston People from Milton, Massachusetts Military personnel from Massachusetts Recipients of the Silver Star Winter Hill Gang United States Army soldiers Criminals from Massachusetts