Steve Flemmi: Crimes, 2003 Guilty Plea, and Where He Is Now

Stephen “The Rifleman” Flemmi is a convicted Boston gangster who ran the Winter Hill Gang alongside James “Whitey” Bulger while secretly working as a top-echelon FBI informant for roughly three decades. Steve Flemmi pleaded guilty in 2003 to involvement in ten murders and is serving life sentences in federal custody, with additional life terms waiting in Massachusetts, Florida, and Oklahoma.¹

The Winter Hill Partnership

Flemmi’s criminal record reaches back to the Boston gang wars of the 1960s, during which he later admitted committing several murders. He became a top-echelon FBI confidential informant in 1965, recruited to help the Bureau’s campaign against La Cosa Nostra.² In 1969, agent H. Paul Rico tipped him that he was about to be indicted for the car bombing of attorney John Fitzgerald, and Flemmi fled. He returned to Boston in 1974 at Rico’s invitation, and the charges were dropped.³

Back in Boston, Flemmi formed a criminal partnership with Whitey Bulger that lasted more than twenty years. The two ran the Winter Hill Gang, a South Boston organization that pulled in millions through extortion, drug trafficking, loan sharking, and illegal gambling.⁴ Bookmakers, drug dealers, and loan sharks paid regular tribute to keep operating. Kevin Weeks, Bulger’s protégé and the trio’s third member, later testified that he collected those payments as a go-between.⁵

Flemmi also connected the Winter Hill Gang to the Italian Mafia through Frank Salemme, who led the New England branch of La Cosa Nostra. The gang’s working relationship with the Patriarca crime family ran mainly through the Angiulo brothers in Boston.⁶

The FBI Arrangement

Starting in 1975, Flemmi and Bulger were jointly handled by FBI agent John Connolly out of the Bureau’s Boston office. The pair fed Connolly intelligence that, combined with electronic surveillance, led to the conviction of nearly every member of the Patriarca family’s Boston branch.⁶

In return, Connolly and his supervisor John Morris warned Flemmi and Bulger when other agencies came looking, declined to build cases against them, and leaked the names of informants cooperating against the gang. The relationship was personal as well as professional. Flemmi and Bulger socialized at Morris’s home and sent along gifts, including wine and plane tickets. Connolly took roughly $235,000 from Bulger and Flemmi over the years.⁷⁸

A congressional investigation later described the Boston FBI office as operating on an “ends justify the means” philosophy, with federal officials actively protecting informants they knew were committing murders and frustrating homicide investigations across multiple states. The arrangement lasted nearly 25 years.⁹

The Ten Murders

Flemmi eventually pleaded guilty to involvement in ten killings. Several are well documented through his testimony and court filings.

Debra Davis (1981)

Davis, 26, was Flemmi’s girlfriend. Flemmi testified that he inadvertently revealed to her that he and Bulger were FBI informants connected to Connolly. Bulger decided Davis had to die because Connolly was “too valuable an asset to compromise.” Flemmi lured her to a South Boston house, where Bulger grabbed her by the throat and strangled her. Flemmi said that when Bulger asked him to finish her, he answered, “I couldn’t do it.” Bulger replied, “I’ll take care of it.” Flemmi helped strip and wrap the body, and the two buried her near the Neponset River. Her remains were recovered from a tidal marsh in 2000 and identified through DNA.¹⁰¹¹

Deborah Hussey (1985)

Hussey, 26, was Flemmi’s stepdaughter. He had begun a relationship with her mother when Deborah was two, and she grew up calling him “Daddy.” Flemmi admitted sexually abusing her, calling it “a moment of weakness.” In January 1985, he drove her to a house where Bulger was waiting. Bulger strangled her with a rope, using a stick to twist it tight. Flemmi then pulled out Hussey’s teeth with pliers to prevent identification, calling the task “very distasteful.” According to Flemmi, Bulger wanted her dead because her drug use, arrests, and loose talk made her a liability.¹²¹³

Roger Wheeler (1981)

Wheeler was an Oklahoma businessman who owned World Jai Alai, a company the Winter Hill Gang was skimming from. When he began investigating the discrepancies, Bulger and Flemmi directed hitman John Martorano to kill him. Flemmi testified that former FBI agent H. Paul Rico provided details of Wheeler’s schedule to make the murder possible.¹⁴

Edward Connors (1975)

Connors, a bar owner, was killed for “telling people Winter Hill business.” Flemmi testified that he and Bulger ambushed Connors at a phone booth, both men firing. Flemmi said he squeezed off seven or eight shots while Bulger emptied a double-barreled shotgun and a pistol.¹⁵

Richard Castucci and Others

Flemmi testified that Connolly told him and Bulger that Castucci was feeding information about them to law enforcement. The pair decided to have him killed, and Martorano carried it out.¹⁵ Flemmi also admitted to killings during the 1960s gang wars and a shooting in a Roxbury garage. Methods included strangulation and shots to the head, followed by burial in shallow graves. Flemmi routinely pulled out victims’ teeth to defeat identification, a habit that earned him the nickname “Dr. Mengele” among associates.⁵

The Immunity Defense That Failed

The arrangement collapsed in January 1995, when Flemmi, Bulger, and Salemme were indicted on federal racketeering, conspiracy, and extortion charges. Connolly tipped off Bulger before the arrests, and Bulger fled. Salemme also ran but was captured. Flemmi was arrested.⁹

Flemmi then tried a novel defense: the FBI had promised him immunity from prosecution as long as he cooperated against the Mafia. A ten-month evidentiary hearing examined the claim in detail. The district court condemned the FBI’s conduct but denied the motion to dismiss.¹⁶

The First Circuit settled the question in United States v. Flemmi, 225 F.3d 78 (1st Cir. 2000). FBI agents, the court held, have no authority to grant immunity. That power rests with United States Attorneys. Because no prosecutor had ratified anything Connolly or Morris may have promised, whatever Flemmi had been told was unenforceable. The FBI’s own internal manual, the court noted, expressly barred agents from offering immunity to informants.²

The 2003 Guilty Plea

In September 2001, Flemmi was charged in a new indictment with ten murders committed while he was an FBI informant. On October 14, 2003, he pleaded guilty in U.S. District Court in Boston to racketeering charges, admitting all ten killings. Under the plea agreement, authorities in Oklahoma and Florida dropped their pursuit of the death penalty. In exchange, Flemmi accepted life in prison without the possibility of parole.¹ The government also seized five of his condominiums, worth roughly $2 million, which were auctioned off in 2002 after an earlier conviction for extortion and money laundering.¹⁷

Cooperation Against Bulger and Salemme

Flemmi became one of the central prosecution witnesses at Whitey Bulger’s 2013 federal racketeering and murder trial in Boston. It was the first time the former partners had seen each other since 1994, and the reunion was ugly. On July 18, 2013, after about ten minutes on the stand, Flemmi shouted a profanity at Bulger and Bulger shouted back. U.S. Marshals stepped between them.¹⁸

Over several days, Flemmi described the partnership as “strictly criminal,” walked through the murders, and said he had been present with Bulger “hundreds of times” when Bulger gave information to the FBI, directly contradicting Bulger’s longstanding denial that he had been an informant.⁴ Defense attorney Hank Brennan pressed Flemmi on his plea deal, his perjury history, and inconsistencies in his accounts of Hussey’s death, at points leaving Flemmi unable to say which version was true.¹⁹ In August 2013, Bulger was convicted on 31 of 32 counts, including involvement in eleven murders, and later sentenced to two consecutive life terms plus five years.¹¹

Flemmi testified again in the 2018 federal trial of Frank “Cadillac” Salemme and Paul Weadick for the 1993 murder of nightclub owner Steven DiSarro, saying he had walked in on the killing during an unexpected visit to Salemme’s home. Both defendants were convicted and sentenced to mandatory life.²⁰

Where Steve Flemmi Is Now

Flemmi is in federal custody, serving life sentences for murders in Massachusetts, Florida, and Oklahoma. In August 2021, at age 87, he sought compassionate release on health grounds. The Florida Commission on Offender Review denied his parole bid, citing his “violent criminal history,” and set his next Florida parole eligibility date at 2028. The commission’s records list a symbolic parole date of the year 2218, reflecting 2,680 months remaining on his Florida sentence alone.²¹²²

1
Los Angeles Times. Boston Mobster Flemmi Admits Killings
2
FindLaw. United States v. Flemmi, 225 F.3d 78
3
Casemine. United States v. Salemme
4
Christian Science Monitor. Whitey Bulger Trial: Rifleman Flemmi Details Murder After Grisly Murder
5
CNN. Kevin Weeks Testifies at Bulger Trial
6
GoLocalProv. Whitey Bulger and Raymond Patriarca: Inside the Relationship
7
The New Yorker. Assets and Liabilities
8
CNN. Connolly Sentenced to 40 Years
9
GovInfo. House Report 108-414
10
WGBH News. Flemmi: Bulger Made Me Kill Debra Davis
11
CNN. Flemmi Testifies Bulger Strangled Davis
12
ABC News. Whitey Bulger Witness Delivered Stepdaughter to Be Murdered
13
CBS News. Flemmi Pins Killing of His Stepdaughter on Former Mob Boss
14
Cape Cod Times. Boston Mobster Flemmi Admits Killings
15
CBS News. Flemmi Testifies Bulger Was Involved in Several Killings
16
Department of Justice Office of the Inspector General. The FBI’s Handling of the Whitey Bulger Matter
17
The Intelligencer. Mobster’s Condos Up for Auction
18
ABC News. Whitey Bulger Ally Stephen Flemmi Exchange Curses
19
WGBH News. Raw Emotion, Sordid Detail Mark Flemmi’s Third Day on the Stand
20
U.S. Attorney’s Office, District of Massachusetts. Former Mafia Boss and Associate Convicted of 1993 Murder
21
Boston Globe. Notorious Boston Gangster Stephen Flemmi Seeks Parole in Florida
22
Patriot Ledger. Mobster Stephen Flemmi Denied Compassionate Release From Prison