John Connolly Tipped Whitey Bulger FBI Agent to Die in Prison After Trial

by editor

James "Whitey" Bulger can credit his place on the FBI's Ten Most Wanted list to one man: John Connolly Jr is the former Boston FBI agent who acted as tipster to the gangster-turned-informant and another mobster about to be indicted. The former Boston FBI man will likely die in prison. It's a strange story of "ethics".
 
It's all straight out of a movie. Pretty much -- Martin Scorsese's 2006 movie, "The Departed", depicts the brutality behind mobster James Bulger. What is not heard is an equally strange story, of a man who's received a harsher prison term than any of the mobsters.
 
John Connolly refused to cut a deal with prosecutors, and refuses to renounce his innocence.
 
Connolly was a decorated FBI agent who one of the primary men involved in developing the agency's Top Echelon Criminal Informants Program in New England. Then the Boston FBI agent was presented with a bit of a problem: Mobster James "Whitey" Bulger and another mob man were about to be indicted, but they'd already been working for John Connolly for 20 years as informants. He tipped off the gangsters about what was about to happen.
 
As to why John Connolly Jr acted as tipster to the two mobsters isn't totally clear. The tip could've been out of some sense of "ethics" after bringing the two men on as FBI informants and working with them for 20 years -- when the government then decided to go after the gangsters. It's plausible Connolly feared he'd wind up dead if the mob men were indicted without any warning -- and therefore perceived disloyalty. Or it could have been some other reason altogether.
 
Following guidelines not far removed from the mob, John Connolly Jr pretty much refuses to speak -- outside of expressing a very deep anger.
 
Apparently the government does not forget -- nor does not forgive -- actions that make the FBI look foolish. The Feds have made John Connolly pay dearly for any 'transgressions' against the agency. John Connolly tipped out two mobsters they were about to go down, when the Feds planned to indict James "Whitey" Bulger and Stephen "the Rifleman" Flemmi in 1995.
 
Mobster James "Whitey" Bulger was able to get the hell out of Dodge in 1995, escaping the city of Boston before cops or the FBI could grab him. But the lesser-known Stephen "the Rifleman" Flemmi did not make that escape. As it turned out, the one that got away has proved far less detrimental to Connolly than the one that didn't: while the government has raked John Connolly over the coals in the escape of James Bulger, it's Flemmi the government's used to put a nail in the former FBI agent's coffin.
 
If once wasn't enough, the government went after Connolly again for a double-whammy in 2008. Connolly says that because he "refused to lie", as the Justice Department wanted him to, the government stuck him with a prison sentence of 10 years in 2003. But that was just round one.
 
With a first conviction for racketeering in 2002 -- charges that put the FBI man in prison since 2003 -- former FBI agent John Connolly will probably die surrounded by prison walls. Now 70, Connolly isn't getting out anytime soon. He may have lived to see another day of freedom had the government not gone after the agent a second time. That time for murder.
 
In 2008, Johny Connolly was convicted on a second-degree murder with a firearm conviction carries a sentence that will add between 30 years to life in prison for John Connolly, a consecutive sentence to the original 2002 racketeering term of 10 years.
 
Jurors in the 2008 murder case against agent Connolly believed testimony provided by multiple gangsters, and one mobster in particular. Ironically that mob man who was testifying under oath is none other than a convicted criminal: Stephen "the Rifleman" Flemmi.
 
Stephen Flemmi was one of the two mobsters Connolly tipped in 1995 of the forthcoming indictment -- and he happens to be the gangster that didn't make it out of Boston before the government grabbed him. James "Whitey" Bulger proved quicker on the draw, already on the run. Reputed gangster James "Whitey" Bulger was on the run until June 22, 2011 when the former Boston mob boss was captured in Santa Monica, California after a tip from an Iceland woman watching an international FBI TV publicity campaign on CNN led to the gangster's capture and arrest.
 
74 years old at the time of Connolly's 2008 murder trial, Flemmi was serving a life sentence for 10 murders. It was 2008 court testimony by mobster Stephen "the Rifleman" Flemmi that threw FBI agent John Connolly in prison permanently: The gangster that didn't escape swears it was a 1982 tip from John Connolly, while Flemmi was working for the FBI agent as an informant, that led to the murder of a Boston-area accountant. That accountant, John B. Callahan, had a very bad fate after socializing with gangsters.
 
Flemmi testified in court that Connolly told him and fellow gangster "Whitey" Bulger the accountant "wouldn't hold up" under pressure -- that Callahan would implicate Flemmi and Bulger in the 1981 murder of businessman Roger Wheeler, who was president of World Jai Alai.
 
To solve that problem, Flemmi and Bulger had Callahan executed. The hit men that did it claim a bullet to the head. The accountant's body was found riddled with bullet holes.
 
Key witnesses for government prosecution -- in the 2008 murder case against John Connolly -- included mobster Flemmi who was serving life in prison for conviction in 10 murders, mobster Martorano who served only 12 years for conviction in 20 murders, former gangster Kevin Weeks who served only five years for assisting "Whitey" Bulger in five murders, and former FBI supervisor John Morris who admitted to accepting $7,000 in bribes from gangsters Bulger and Flemmi and admitted to leaking the mob men information.
 
The prosecution's crew of witnesses didn't exactly have the best reputation.
 
But so it came to be that -- after testimony from known criminals and mob men, and one admittedly dirty boss -- FBI agent John Connolly went down for murder in 2008.
 
There's an irony here: Former FBI agent John Connolly has a prison term that blows past any jail sentences of involved mobsters.
 
Bob Fitzpatrick, commander of the FBI's organized-crime squad and John Connolly's former boss says: "The Department of Justice threw him under the bus."
 
John Connolly calls federal prosecutors, cops who investigated the former FBI agent, and mobsters who took deals to ensure his life behind bars, "liars" and "bastards."
 
"I am a prisoner of war," the current Federal Correctional Complex Butner inmate (Register 22928-038) told Boston Magazine in 2008.
 
If the Butner correctional facility sounds familiar, it's the same prison housing pyramid-schemer Bernard "Bernie" Madoff (Register 61727-054). The place is kind of famous like that. Federal Correctional Complex Butner has also housed famous criminals including televangelist Jim Bakker and President Ronald Reagan's attempted assassin John Hinckley Jr.
 
The story of John Connolly Jr is an intriguing one that best begins with Boston Magazine's David Boeri -- who makes a fascinating story unforgettable -- with "The Martyrdom of John Connolly". Read it: you won't be disappointed.

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