Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger.

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.

He was ultimately brought up on charges under the Racketeer Influenced and Corrupt Organizations Act, and pleaded guilty in return for a sentence of life in prison.

[2] He was raised in the Orchard Park tenement located at 25 Ambrose Street in the Roxbury neighborhood of Boston, Massachusetts.

[3] His father was a bricklayer and veteran of the Royal Italian Army during World War I, and his mother was a full-time homemaker.

[4] 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.

"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.

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.

It is thought that Flemmi, Bulger, and Weeks lured her to the house at 799 East Third Street in South Boston and garrotted her.

[10]: 248  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.

[10]: 215  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.

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.

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.

In 2000, Flemmi's brother Michael, then a retired Boston Police Department 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.

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.

[11]: 341–342 [12] Flemmi testified against Connolly at the latter's trial for the murder of John Callahan, the former president of World Jai Alai.

According to Flemmi, Connolly told him and Bulger that Callahan could potentially turn state's evidence and implicate them in Wheeler's murder.

Stephen Flemmi and Whitey Bulger are alleged to have committed statutory rape 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.