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Notorious Boston gangster Stephen Flemmi DENIED release after serving 26 years of life sentence

Stephen ‘The Rifleman’ Flemmi, the once-loyal partner of Boston gangster James ‘Whitey’ Bulger, has been denied compassionate release by the Florida parole board Wednesday

Notorious Boston mobster Stephen Flemmi was denied compassionate release Wednesday by the Florida parole board as he serves out his 26th year of a life sentence.

Flemmi, 87, was the once-loyal partner of gangster James ‘Whitey’ Bulger and is linked to at least 10 killings in Massachusetts, Oklahoma and Florida.  

Nicknamed ‘The Rifleman’, he is serving out his life sentence at an undisclosed prison in Florida for first-degree murder, illegal possession of a machine gun, a shotgun, silencers, money laundering and conspiracy.  

A loved one of one of his victims slammed Flemmi as a ‘modern-day Charles Manson’ as he opposed his release. 

In his application for compassionate release in July, Flemmi cited health concerns over the coronavirus. 

He wrote in his application that he ‘cooperated with the Federal Government in a series of cases against extremely violent individuals with a long and storied history of retribution against cooperators and as a result I am being housed in a confidential location with the [US Bureau of Prisons].’  

Flemmi also applied for compassionate release in Oklahoma, where he was sentenced for the killing of a businessman. He would have needed both Oklahoma and Florida to agree to his release. 

Nicknamed 'The Rifleman', Flemmi is serving out his life sentence at an undisclosed prison in Florida for first-degree murder, illegal possession of a machine gun, a shotgun, silencers, money laundering and conspiracy. Flemmi is pictured in a 1980s mugshot

Flemmi also applied for compassionate release in Oklahoma, where he was sentenced for the killing of a businessman. He would have needed both Oklahoma and Florida to agree to his release.

Nicknamed ‘The Rifleman’, Flemmi is serving out his life sentence at an undisclosed prison in Florida for first-degree murder, illegal possession of a machine gun, a shotgun, silencers, money laundering and conspiracy. Flemmi is pictured in a 1980s mugshot

FBI surveillance footage of Flemmi and James 'Whitey' Bulger. Once on the FBI's Most Wanted List, Bulger and Flemmi were partners. Flemmi eventually testified against him at trial in 2013

FBI surveillance footage of Flemmi and James ‘Whitey’ Bulger. Once on the FBI’s Most Wanted List, Bulger and Flemmi were partners. Flemmi eventually testified against him at trial in 2013

Flemmi's relationship with Bulger dates back to the 1960s. Bulger ran the Winter Hill Gang that terrorized Boston for decades.

Flemmi’s relationship with Bulger dates back to the 1960s. Bulger ran the Winter Hill Gang that terrorized Boston for decades.

In 2004, Flemmi pleaded guilty to the 1981 killing of Tulsa businessman Roger Wheeler in 2004. He is serving a life sentence made up of multiple federal and state sentences, having reached a deal with the United States government to avoid the death penalty in exchange for turning informant on Bulger, according to the Boston Globe

At the same time he also pleaded guilty in federal court in Boston to 10 murders in the 1970s and 1980s among other crimes, including extorting drug dealers, bookmakers, and legitimate business people. He admitted to participating in about 50 killings dating back to Boston’s gang wars in the 1960s, and admitted to committing heinous crimes, like pulling the teeth of victims before burying them in unmarked graves. 

Under state law at the time of Flemmi’s killing of Boston businessman John B. Callahan in 1982, he must serve a minimum of 25 years in prison before he is eligible for parole.  

Flemmi testified that he lured his own stepdaughter, Deborah Hussey, to be strangled to death by Bulger. He also accused Bulger of molesting Hussey. Flemmi himself was accused of doing the same, but claimed they were consensual, despite Hussey calling him 'Daddy.'

Flemmi testified that he lured his own stepdaughter, Deborah Hussey, to be strangled to death by Bulger. He also accused Bulger of molesting Hussey. Flemmi himself was accused of doing the same, but claimed they were consensual, despite Hussey calling him ‘Daddy.’

Debra Davis was killed by Flemmi and allegedly Bulger in 1981. Her brother Steve testified against Flemmi at the hearing, saying he 'doesn't even deserve to breathe'

Debra Davis was killed by Flemmi and allegedly Bulger in 1981. Her brother Steve testified against Flemmi at the hearing, saying he ‘doesn’t even deserve to breathe’ 

Flemmi’s had close ties to with Bulger dating back to the 1960s. Once considered behind only Osama bin Laden on the FBI’s Most Wanted list, Bulger ran the Winter Hill Gang that terrorized Boston for decades. 

He later became an FBI informant, like Bulger, and testified against him in 2013, accusing him of molesting and strangling his teenage stepdaughter Deborah Hussey. 

Flemmi was also accused of molesting Hussey but claimed the encounters were consensual, even though Hussey referred to Flemmi as ‘Daddy.’

In July when it was revealed he was seeking a release, his estranged son William St. Croix, Hussey’s brother, expressed skepticism. 

‘I don’t know how someone can redeem themselves after doing all the vile things he’s done,’ St. Croix said. 

‘Even if he was redeemed, I would still always live with the fear that if he’s out that he might harm my children.’ 

Bulger was murdered by fellow inmates at a West Virginia prison just hours after arriving in 2018. He was transferred there to continue to serve out consecutive life sentences. 

Flemmi's had close ties to with Bulger (pictured) dating back to the 1960s. Once considered behind only Osama bin Laden on the FBI's Most Wanted list , Bulger ran the Winter Hill Gang that terrorized Boston for decades

Flemmi’s had close ties to with Bulger (pictured) dating back to the 1960s. Once considered behind only Osama bin Laden on the FBI’s Most Wanted list , Bulger ran the Winter Hill Gang that terrorized Boston for decades

Flemmi (pictured) later became an FBI informant, like Bulger, and testifed against him in 2013, accusing him of molesting and strangling his teenage stepdaughter Deborah Hussey

Flemmi (pictured) later became an FBI informant, like Bulger, and testifed against him in 2013, accusing him of molesting and strangling his teenage stepdaughter Deborah Hussey

Flemmi testified against both former mob allies and corrupt FBI agents. 

His daughter, Jeanette Benedetti, spoke in favor of his release. She said he’s become a ‘model prisoner’ who can ‘speak several languages.’ 

Despite the requests, the relatives of Flemmi’s victims were not made aware of what he was doing and outraged at the idea of him leaving prison.  

‘I think the government should be notifying all the families as to what’s going on,’ said Steve Davis, whose 26-year-old sister, Debra Davis, was killed by her then-boyfriend Flemmi, and allegedly Bulger, in 1981. 

‘If he was to die right now, maybe I’d be at ease with it. To know he’s still breathing and out there… I think he should die right now, die in prison.’ 

Davis said by phone that Flemmi had ‘ruined more families that you can imagine’, and added that the serial killer had pulled out his sister’s teeth after killing her so that she couldn’t be identified.  

He added that Flemmi ‘doesn’t even deserve to breathe.’

The board set Flemmi’s parole date for the year 2218. His next review has been pushed back another seven years, when he will be 93 years old.


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