Stephen Flemmi: Murders, FBI Informant Role, and Plea Deal

Stephen “The Rifleman” Flemmi is a Boston mobster who pleaded guilty to ten murders and spent roughly three decades as a secret FBI informant while running one of the most violent criminal enterprises in New England history. Born June 9, 1934, he was the top lieutenant to James “Whitey” Bulger in the Winter Hill Gang and is now 90 years old, serving two life sentences plus 30 years in an undisclosed federal prison.¹

Who He Is and Where the Nickname Came From

Flemmi earned “The Rifleman” during the Korean War, where his marksmanship stood out. He later told his longtime girlfriend Shirley Grispi that he killed enemy soldiers by shooting them and bludgeoning them with the butt of his rifle.² He appeared in FBI records as early as 1958.¹

His brother Vincent “Jimmy the Bear” Flemmi was also a violent gangster and an FBI informant who committed multiple murders in the 1960s with the Bureau’s knowledge; a June 1965 FBI memo listed seven of Vincent’s victims.³

Decades as an FBI Informant

Flemmi began feeding information to the FBI in the 1960s about La Cosa Nostra’s New England operations. By 1967 the Bureau had designated him a “top-echelon informant,” meaning a source expected to deliver a steady stream of intelligence about organized crime leadership.⁴ His first handler was Agent H. Paul Rico, who Flemmi said promised him protection from prosecution.

That protection went beyond looking the other way. After a state grand jury indicted Flemmi in 1969 for a car bombing and a murder, he said Rico advised him to flee Massachusetts. He spent more than four years as a fugitive and returned, he claimed, only after Rico assured him bail would be granted and the charges dropped.⁴

Around 1975 his informant work merged with Bulger’s. For roughly 15 years the two fed information to the FBI together, with Agent John Connolly and supervisor John Morris as their primary handlers.⁵ Flemmi later testified they gave the FBI intelligence “hundreds of times,” including diagrams of Mafia gathering locations.⁶ The FBI officially closed him as an informant in 1990.

Through the 1970s and 1980s, Flemmi served as Bulger’s top lieutenant in the Winter Hill Gang, which dominated organized crime in South Boston.⁷ The enterprise ran on extortion of drug dealers, bookmakers, and business owners, plus drug trafficking, money laundering, and murder. Flemmi also carried out murders at the direction of New England Mafia boss Francis “Cadillac Frank” Salemme, a dual allegiance that made him unusually powerful in Boston’s underworld.⁸

The Ten Murders

Flemmi has admitted involvement in far more killings than the ten to which he formally pleaded. In 2018 testimony he acknowledged being involved in “probably about 50” murders.¹ The ten he pleaded guilty to were James Sousa, Edward Connors, Thomas King, Richard Castucci, Roger Wheeler, Debra Davis, John Callahan, Arthur Barrett, John McIntyre, and Deborah Hussey.⁹

Several of the killings happened at a single South Boston house that came to be called the “death house.” Flemmi testified that Bulger lured suspected informants there, and that after the murders the gang removed the victims’ teeth to prevent identification and buried the bodies in the basement. Those bodies were not discovered until 2000.¹⁰

Two of the killings stand apart because the victims were close to Flemmi personally. Debra Davis was his girlfriend of nearly ten years. In 1981, Flemmi later testified, Bulger insisted she be killed because she had learned of Bulger’s dealings with a corrupt FBI agent. Bulger strangled her, and her body was buried along the Neponset River in Quincy.¹¹

Deborah Hussey was Flemmi’s stepdaughter. He had begun a relationship with her mother when Deborah was two, and she grew up calling him “Daddy.” In January 1985, Flemmi drove Hussey to a house where Bulger strangled her by crushing her windpipe from behind.¹² Flemmi admitted pulling out her teeth with pliers afterward.¹³ At Bulger’s 2013 trial, pressed by defense counsel on allegations he had sexually abused Hussey, Flemmi admitted to a sexual relationship with her but described the encounters as moments of “weakness.”¹⁴

Other victims died for a common reason: someone inside the FBI had told Flemmi and Bulger they were talking to law enforcement. Nightclub owner Richard Castucci was killed after Connolly warned the pair he was informing on them, with hitman John Martorano carrying out the murder at their direction.¹⁵ Boston businessman John Callahan was killed by Martorano in Miami in 1982 after Connolly allegedly warned Bulger and Flemmi that Callahan would expose them if he cooperated with authorities.¹⁶ Tulsa businessman Roger Wheeler, owner of World Jai Alai, was murdered at a country club in 1981; Flemmi accused former agent Rico of helping arrange the hit by providing Wheeler’s schedule.¹⁷

The FBI Corruption His Case Exposed

What a federal judge called a “Faustian bargain” allowed Flemmi and Bulger to commit murders and run their enterprise while corrupt agents shielded them, tipped them to wiretaps, and identified rival informants who were then killed.

Connolly handled the pair from the 1970s until his 1990 retirement. He was indicted in December 1999 on racketeering, obstruction of justice, and conspiracy charges.¹⁸ Flemmi later testified that he and Bulger paid Connolly $235,000 over the course of their relationship.¹⁶ In May 2002 a federal jury convicted Connolly for tipping the pair to their 1994 indictment; he was sentenced to 121 months. In 2008 a Florida jury convicted him of second-degree murder for his role in the Callahan killing, relying heavily on testimony from Flemmi and Martorano.¹⁹

Connolly’s supervisor, John Morris, admitted taking $7,000 in bribes from Flemmi and Bulger, tipping them to wiretaps, and warning them about informant Brian Halloran, who was subsequently murdered. Morris received immunity in exchange for testifying against Connolly.¹⁶

Rico, Flemmi’s original handler, was arrested near Miami in October 2003 and charged with murder and conspiracy in the Wheeler killing. After leaving the FBI he had become head of security for World Jai Alai, Wheeler’s company, and investigators alleged he had provided Martorano with Wheeler’s schedule.¹⁷ Rico died in a prison hospital while awaiting trial.³

Arrest, Plea Deal, and Life Sentence

On January 10, 1995, Flemmi, Bulger, and several co-defendants were indicted on racketeering, racketeering conspiracy, Hobbs Act extortion, conspiracy to commit extortion, and suborning perjury. Bulger fled before the indictment issued, tipped off by Connolly, and would remain a fugitive for 16 years. Flemmi was arrested and has been in custody since.⁴

Flemmi initially fought the charges by arguing that FBI agents had granted him immunity. Judge Mark Wolf agreed in a pretrial ruling, finding Connolly and Morris had promised immunity for information gathered during electronic surveillance at three locations. In September 2000 the First Circuit reversed, holding that FBI agents lack the authority to grant immunity because that power belongs exclusively to United States Attorneys.⁴

With the immunity defense gone, Flemmi took a deal. On October 14, 2003, he pleaded guilty to all counts in a superseding federal indictment, including ten murders, cocaine and marijuana trafficking, extortion, obstruction of justice, money laundering, perjury, and firearms offenses.⁹ He also pleaded guilty to state first-degree murder charges in Oklahoma for Wheeler and in Florida for Callahan.²⁰ On January 27, 2004, he was sentenced to life in federal prison, with a separate Miami life sentence for Callahan carrying a minimum of 25 years before parole eligibility under Florida law. The deal spared him the death penalty that prosecutors in both Oklahoma and Florida had been pursuing.²¹

What His Cooperation Delivered

Flemmi took the stand in July 2013 at Bulger’s federal racketeering trial. It was the first time the two former partners had faced each other in court since 1994, and the encounter was openly hostile; after Flemmi’s first day of testimony on July 18, the two exchanged obscenities as court adjourned, and U.S. Marshals positioned themselves between them to block eye contact.²² Flemmi described the death-house killings, confirmed Bulger’s status as an FBI informant, and testified that after some killings Bulger would “take a nap or relax in an upstairs room.”¹⁰ Bulger was convicted on 31 counts, including involvement in 11 murders.

In 2018 Flemmi was the government’s star witness against Salemme and co-defendant Paul Weadick for the 1993 murder of nightclub owner Steven DiSarro. Flemmi testified he had unexpectedly walked into Salemme’s home and witnessed Salemme’s son strangling DiSarro while Weadick held his legs and Salemme watched.²³ The defense called Flemmi a “sociopath” and an “absolute liar” chasing a sentence reduction, but the jury convicted both men after a seven-week trial.²⁴ Salemme was sentenced to life in September 2018.²⁵

Government Liability to Victims’ Families

Families of Flemmi’s victims sued the United States, arguing the FBI’s negligent handling of its informants made the Bureau liable for the murders. Federal Tort Claims Act suits filed in 2002 and 2003 by the families of Debra Davis and Deborah Hussey produced a finding of government negligence. The district court awarded $350,000 to each estate for pain and suffering, plus $1 million to the Davis estate for loss of consortium on behalf of Debra Davis’s mother, and the First Circuit affirmed those awards in January 2012.¹²²⁶ In a separate state proceeding, Norfolk Superior Court awarded $33.5 million to the Davis estate in September 2009.²⁷

Where He Is Now

Flemmi has been locked up since January 1995 and is serving two life terms plus 30 years across his federal, Oklahoma, and Florida sentences.¹ He is housed at an undisclosed federal prison as part of the Witness Security Program and does not appear in the public Bureau of Prisons database.

In August 2021, when he was 87, the Florida Commission on Offender Review denied his petition for compassionate release, citing his “violent criminal history.” His daughter, Jeanette Benedetti, told the commission he was a “model prisoner” and a “peacemaker” who was remorseful, an avid painter, and could speak several languages.²⁸ The commission set his next parole eligibility date for May 4, 2218, with 2,680 months remaining on his sentence, and told him he could reapply in seven years, when he would be 93.²⁹ He turned 90 on June 9, 2024.

1
Boston Herald. Happy 90th Birthday to Stephen The Rifleman Flemmi
2
Boston Magazine. Rifleman Flemmi Girlfriend Story
3
Boston Herald. The Grisly Story of Jimmy the Bear
4
FindLaw. United States v. Flemmi, 225 F.3d 78
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WGBH News. Flemmi Says He and Bulger Were FBI Informants
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CBS News. Whitey Bulger Trial: Ex-Associate Details Role as FBI Informant
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Britannica. Winter Hill Gang
8
WGBH News. Former Mob Enforcer Recounts Murders at Boss Frank Salemme’s Request
9
DEA. Flemmi Sentenced
10
Christian Science Monitor. Whitey Bulger Trial: Rifleman Flemmi Describes Death House Murders
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BBC News. Flemmi Testifies on Killings at Bulger Trial
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U.S. Court of Appeals, First Circuit. Davis v. United States
13
ABC News. Whitey Bulger Witness Delivered Stepdaughter to Be Murdered
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Reuters. Boston Home Was Death House for Whitey Bulger Victims
15
CBS News. Whitey Bulger Trial: Flemmi Testifies on Killings
16
Boston Magazine. The Martyrdom of John Connolly
17
Seacoast Online. Former Boston FBI Agent Arrested
18
U.S. Court of Appeals, First Circuit. United States v. Connolly
19
Boston Herald. Ex-FBI Agent Zip Connolly Cites Secret Whitey Bulger Manuscript
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Boston Globe. Boston Gangster Stephen Flemmi Is Seeking Compassionate Release
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Los Angeles Times. Mobster Pleads Guilty to Racketeering
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ABC News. Whitey Bulger Ally Stephen Rifleman Flemmi Exchange Curses
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VOA News. Octogenarian Ex-New England Mob Boss Convicted in ’93 Slaying
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NBC Boston. Sentencing for Ex-Mafia Boss Cadillac Frank in Killing
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WGBH News. Former Mobster Frank Salemme Found Guilty of Murder
26
FindLaw. Davis v. United States (First Circuit, 2012)
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Patriot Ledger. Family of Mobster’s Murdered Girlfriend Awarded Damages
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Boston Herald. Stephen Flemmi Denied Compassionate Release in Florida
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Patriot Ledger. Mobster Stephen Flemmi Denied Compassionate Release From Prison