Winter Hill Enterprise


Winter Hill gang founded by: James “Buddy” McLean

Located: Somerville, Massachusetts

Ethnicity: Irish, Italian

 Historical Leadership of the Winter Hill gang :

Citizen Somerville

 Members and associates:



The Secret Life of Whitey Bulger and the Winter Hill Gang:


Until the Fed’s busted him in 2011, Boston gangster James “Whitey” Bulger was the FBI’s most wanted man, arrested while Number One on the America’s Most Wanted, after the murder of Bin Laden, by Navy Seals assassins.The greatest criminal mastermind of our time.  On the eve of his trial, all his shocking secrets will soon come to light–even the one our JUSTICE SYSTEM IS DESPERATE TO CONCEAL.After 16 years on the lam, Boston’s most notorious gangster, James J. “Whitey” Bulger, was captured without incident in Santa Monica, California.The day that many Bostonians though would never happen had arrived, closing an infamous chapter in the city’s history of Organized Crime.Twists and  turns of Whitey’s long violent criminal record filled with tales of double-crosses, ironic shifts and colorful real live characters that it reads like fiction but is supported with real live facts was a fitting climax to the Boston’s FBI’s long relationship with the dark side of the United States Department of Justice.


Outlaw Empires South Boston Irish Mob



The Winter Hill Gang had a notorious reputation due to not only the actions of Flemmi and Bulger personally, but their enforcers as well. John V. Martorano ,Kevin “Two”Weeks” Weeks, Kevin P. O’Neil.Salemme’s partnership with Bulger, Flemmi and FBI agent Connolly combined the New England Mafia wit the Winter Hill gang into what is now called the Enterprise (aka) The Bulger Group.

Brian Halloran

The murders of Brian Halloran, Michael Donahue, Richard Castucci, and John  Callahan are attributed to the Bulger Group through the admissions from Martorano and WeeksHalloran was an informant against Bulger and Flemmi, slain in an ambush on Northern Avenue, May 11, 1982. Donohue was killed in the ambush the son of a Boston Police Detective, while giving Halloran a ride home.Castucci was an informant against Bulger and Flemmi. He was shot in the head and left in a car in Revere, Massachusetts, December 1976.Callahan was a potential witness against Bulger and Flemmi. He was shot and dumped in the trunk of his Cadillac in Miami, August 1, 1982, others murders are connected to the Bulger Group well over 31 murders.


FBI agent Buckley and at least 20 Boston Police Officers and numerous Massachusetts State Police Troopers and detectives received cash payments from the Bulger Group according to FBI informants. witnesses: Salemme, Weeks, Martorano, Flemmi and  others. FBI agent Morris, whom received immunity  admitted to the cash payoffs from Bulger and Flemmi.Before he was discovered to be a TOP ECHELON FBI INFORMANT While executing his alleged 19 hits–strangling and stabbing his victims, dismembering their bodies and yanking out their teeth with pliers to thwart identification Bulger and his partner, Stephen “The Rifleman” Flemmi, ruled the New England rackets for decades. All the while, it had long since been revealed, they were what is known as TOP ECHELON FBI INFORMANTS, of TE’s. They were FBI assets.While Bulger and Flemmi ran New England’s underworld, they were protected and allowed to remain active by high-ranking officials within the Department of Justice as the Public records so supports.The FBI claims that after a 16-year manhunt it finally got wind of Bulger’s whereabouts after disseminating a 30-second public-service ad focused on his female companion, the elegant Greig, a former dental hygienist who was known to frequent beauty and nail salons.

South Boston is a neighborhood in the true sense of the word–an Irish American enclave physically and psychologically separate from the rest of the city.It even has its own song: “Southie Is My Home-town.”In the Old Harbor housing project, three Irish American youths were born before World War II to a shared destiny: One would reach the lofty heights of the famously clannish Massachusetts political machine, one would rise to the highest ranks of national law enforcement, while the third would seize the bloody crown of the New England underworld.All three would end up embroiled in a scandal that reached the highest levels of the American justice system. Whitey Bulger got his elementary education in crime as a teenager running with a Southie street gang known as the Shamrocks.He became a journeyman criminal in league with a  crew of bank robbers while still in his 20s and was named to the FBI‘s most wanted list. Bulger did his first major prison stretch at the federal penitentiary in Atlanta.



Billy Bulger

Whitey’s younger brother Billy took the opposite road. He became a “triple eagle” graduate of Boston College High School, Boston Collage and Boston College- Law School before entering local politics.After 17 years as the President of the State Senate, Billy was named President of the University of Massachusetts.Later, after his gangster brother absconded from the law in 1995, Billy was hounded out of PUBLIC LIFE by the then Massachusetts governor Mitt Romney for refusing to testify before a federal grand jury investigating Whitey.Like most kids in the neighborhood, young Johnny Connolly was in awe of Whitey. He heard the stories of  Whitey having an affair with a stripper from the Old Howard burlesque hall and running off with a traveling circus while most kids were still in school.But Connolly was closer in age to Billy Bulger, and they became friends. Connolly chose to follow Billy’s lead. He got a good education before embarking on a career in law enforcement with the FBI .

Former FBI agent Connolly


As a young street agent in Manhattan, FBI agent Connolly was walking along Third Avenue on a cold December day in 1972 when he recognized fugitive Boston Mafioso Francis “Cadillac Frank” Salemme, a suspected serial killer, Salemme was walking toward him.Salemme was a suspect in numerous gangland hits since the 1960s and had been indicted for planting a car bomb that blew one of the legs off a Boston attorney whom later became a 7th Circuit Court of Appeals Judge Fitzgerald.After a foot chase that ended when Connolly tackled Salemme at the corner of 81st Street, Connolly took the fugitive into custody virtually single-handedly.With the Salemme arrest, Connolly got his wish: he was transferred back to his home town to work the underbelly of Boston, where both the Irish and Italian mobs were thriving even as they warred for dominance.By the time he retired, in 1990, John Connolly had received a distinguished service award, presented to him by then FBI director William Sessions.During his tenure with the Bureau, Connolly proved particularly adept at “Flipping” ranking mobsters, getting them to roll over and snitch by providing vital secret information on organized crime.His FBI superiors ordered Connolly to cultivate Top Irish gangsters as potential secret informers on the Dreaded Italian Mafia.He was from the neighborhood and knew these guys from when they were kids, he told, so why not give it a try?

w bulger
Billy Bulger

Through his old friend Billy Bulger ( NOW Former Senate president of the Massachusetts Senate for over 17 years), Connolly approached Whitey Bulger.As Connolly tells it, they arranged for a late-night meeting in a parked car overlooking Boston Harbor in September 1975.In the car Connolly played Bulger a tape of wiretapped phone conversation between Jerry Angiulo, head of the Boston’s arm of The Mafia, and a Mafia hit man. Anguilo had put out a contract to have Bulger killed.Bulger thanked Connolly for the tip, but he declined to help the FBI.He went back and talked to his partner Stephen “The Rifleman” Flemmi a killer in the Winter Hill gang, and learned that the Rifleman had already signed on to the FBI’s TOP ECHELON informant program.Bulger changed his mind and entered the rarefied, treacherous informant program.As FBI assets, Whitey Bulger and Stephen Flemmi were  FBI agent Connolly’s top performers.They supplied invaluable inside mob intelligence to the FBI for more than 15 years.

That information often constituted the probable cause the feds needed to get warrants, plant bugs and  mount wiretaps, which provided United States Department of Justice prosecutors evidence to indict and convict the entire hierarchy of the New England branch of the Mafia, the long indomitable Patriarca crime family, ruled by Mafia commission member Raymond L.S. Patriarca and later by his son Ray Junior, (NOW in retirement). Working out of their headquarters–Triple O’s bar in South Boston and later a Lancaster Street garage ,Bulger now ran his criminal empire with the support of numerous FBI agents (Connolly, Buckley etc), Massachusetts State Police detectives, DEA agents Joseph Desmond (Jack Salemme’s handler), Boston Police Bomb Squad Detectives Michael Flemmi.


Bulger, with his fingers on the quickening pulse of the heat, Bulger  knew that with the changing of the guard in New England’s federal law enforcement chain of command it was time to get out of town.Bulger after receiving his tip from FBI agent: Buckley and Quinn’s intelligence whom informed agent Connolly of the 1995 indictments of Salemme, Flemmi and Bulger, allowed Bulger and Salemme to successfully flee.Bulger scooped up his main squeeze, a single mother named Teresa Stanley, and together they set off on a leisurely cross-country motor trip.

wyshakNew Assistant United States Attorney: Fred Wyshak had arrived in Boston with an agenda: Take down Bulger and Flemmi, even if it meant exposing the FBI’s secret TOP ECHELON (TE) PROGRAM in the process.Wyshak teamed with prosecutor: Brain Kelly. and soon they were making cases against low-level bookmakers and loan sharks, with their sights set on the WINTER HILL GANG’s bosses: James “Whitey” Bulger and Stephen “The Rifleman” Flemmi.The prosecutors called on Bulger and Flemmi‘s former handler, who by then had already retired from the Bureau.

When FBI agent Connolly was told the prosecutors were investigating his TE informers for crimes including bookmaking and loan sharking, Connolly maintained that the FBI and higher-ups in the United States Department of Justice had GIVEN THE INFORMERS IMMUNITY for “Anything but murder.”Wyshak informed Connolly that that deal was now off the table.They were going to take down Whitey and his partner, the Rifleman.The new regime in the Boston federal prosecutor’s office urged Connolly to go along with the program and deny there had ever been an arrangement with  Bulger and Flemmi which granted them immunity from prosecution for any crime except murder under The Super Secret United States Department of Justice/ FBI’s TOP ECHELON Informant Program. FBI agent: Connolly was adamant: no deal. He refused to lie about the arrangement, which had been underwritten and ratified by his superiors, including the former: U.S. Attorney in Boston, Jeremiah T. O’Sullivan.

If Connolly lied and Bulger went down, the former FBI man (not to mention his family) could find himself in Bulger’s cross hairs.Besides, Connolly says, both his direct FBI superior in the 1980s, John Morris, and O’Sullivan asked Connolly to arrange meetings for them with the crime boss. O’Sullivan and Bulger met in a Boston hotel room. Bulger and Flemmi went to dinner at FBI agent Morris suburban home, where they enjoyed a lavish wine-soaked meal together and exchanged gifts, as well as payoffs from Bulger and Flemmi to FBI agents: Connolly, Buckley, and Morris.

Former FBI agent John Morris

FBI agent John Morris, supervisor of the FBI’s New England Organized Crime Squad, later testified under oath & a grant of immunity from prosecution admitted to taking cash and gifts from the gangsters: Bulger and Flemmi to protect them from their enemies (according to the government: Marino and Ponzo, et al.,) and law enforcement investigations.The fine line between cops and criminals became obscured. Their mandate: Do whatever it takes to bring down the dreaded Italian Mafia.When the indictments against Bulger, Flemmi and Salemme were unsealed in 1995, Flemmi was arrested in a restaurant he was renovating near Faneuil Hall in downtown Boston.But where was Bulger and Salemme? They had vanished. Upon receiving a TIP from FBI agent: Connolly, whom was monitoring the federal grand jury in Boston, through his contacts: FBI agents: Buckley and Quinn and Assistant United States Attorney: Jeffrey Auerhahn.

The FBI was forced to admit Bulger and Flemmi had been TOP ECHELON FBI informants.But the prosecutors and the United States Department of Justice higher-ups were loath to acknowledge that as TOP ECHELON (TE’s) informants they had been given IMMUNITY from prosecution to commit any crime short of murder in exchange for their intelligence.Connolly refused to play along, and as a result he became the United States Department of Justice‘s whipping boy, its scapegoat. As FBI agent: Connolly was NOT the only FBI agent involved in the Greatest Corruption in the United States history. As FBI agents: Michael J. Buckley, John Morris, James Ring, John Newton, Robert Callen, Nick Gianturco, James Greenleaf, etc.. were also culpable, as well as Assistant United States Attorney’s: Auerhahn, Young, O’Sullivan, etc…..

By October 2000 Connolly had been charged with nine counts of criminal action, including racketeering, obstruction of justice and making false statements to a law enforcement FBI officials.Essentially the government prosecutors attempted to prove that instead of merely handling his WINTER HILL GANG informants, FBI agent: Connolly had joined Bulger, Flemmi and Salemme as an active member of his gang.The trial had the city of Boston riveted. Connolly was found GUILTY of racketeering, obstruction of justice and making false statements.

Bulger was gone, and the Feds needed to save face. Using testimony from a WINTER HILL GANG insiders (testimony that was Salemme, then Boss of the New England Mafia and admitted serial killer: John Martorano, admitted to killing over 50 people, a  jury found FBI agent Connolly guilty of tipping off Salemme, Bulger and Flemmi to the impending indictments so he could flee before the law came for him. The judge sentenced FBI agent: Connolly to 10 years in federal prison.Seven years later, FBI agent Connolly was wrapping up his federal bid when he was charged in Miami with conspiring with Bulger, Flemmi and Martorano from the WINTER HILL GANG and others to murder a shady Boston businessman named John Callahan.The former president of World Jai Alai, Callahan was involved in a scam with Bulger and Flemmi until he was found riddled with bullet holes at the Miami airport in the trunk of his Cadillac.The charge claimed that FBI agent Connolly had tipped Bulger, Flemmi and Martorano off that Callahan was going to drop a dime on him for the murder of World Jai Alai owner Roger Wheeler.Callahan’s body had been found with one dime facing up on his chest.

Former FBI agent Connolly

FBI agent Connolly was transferred from the federal prison in Butner North Carolina to the Turner Guilford Knight Correctional Center in Dade County, Florida.He was held in the hole on a 24-hour-a day lock down.At the Miami trial, prosecutors trotted out a rogues’ gallery of hit men and snitches to testify the same type of people that FBI agent: Connolly associated with and conspired with to create and manufactured cases against by coaching witnesses to falsely testify against Italian/Americans at their trial.As FBI agent: Connolly stated to them it was in all of their best interest to take Connolly’s offer for them to become a governmental informant such is the cases of Flemmi, Bulger, Mercurio, Mele, Laface, Mark Rossetti, St. Laurent, all PUBLICLY KNOWN FBI informants/PUBLICLY KNOWN witnesses.



Bullets Over Boston The Irish Mob(Nat Geo tv)


FBI agent: Connolly’s supervisor: John Morris again took the witness stand and wept through his testimony. Although he admitted to accepting thousands and thousands in cash and   other expensive gifts from their TOP ECHELON FBI informants: Bulger, Flemmi etc (Bulger called Morris Vino for his fancy palate), FBI agent: Morris testified against his underling agent: Connolly and walked without ever speeding a minute behind bars, even-though he was culpable in numerous FBI informants being assassinated by tipping off Bulger and Flemmi on other people whom were proving information to law enforcement and potential witnesses against Bulger and Flemmi so that Bulger and Flemmi could eliminate their problems through serial acts of murder to prevent their prosecution for other murders.

John Martorano

Hit man turned government witness John Martorano–who admitted to committing the actual murder of Callahan and placing the dime on the victim’s  chest after shoving the body into the trunk of his Cadillac–testified against FBI agent: Connolly.Today Martorano, known as the Boston Basin Street Butcher and with more than 50 confirmed notches in his belt depicting murders he committed, is a free man often seen  dining in the finest Boston restaurants.Another admitted murderer who testified against Connolly in exchange for a lesser sentence is Bulger’s partner: Stephen “The Rifleman” Flemmi, also admitting to killing over 20 people and is now deemed a highly credible governmental expert witness in the art of killing and testifying against current and former FBI  agents and prosecutors for the government, whom spared him the death sentence in return.Connolly was convicted of second-degree homicide with a firearm and sentenced to 40 years in prison–a virtual life sentence.

It appears that FBI agent Connolly’s might be experiencing KARMA, for all of his historic and current corruption while an FBI agent in the Boston Office and setting up numerous murders.Although, he is not the only FBI agent culpable. FBI agents: Michael J. Buckley seemed to escaped culpabilities as he was Connolly’s partner in crime. Although the statute of limitations did NOT run out as Buckley fraudulently testified at Connolly trial in 2008, committing perjury by falsely stating on record that he did not receive cash payoffs from Flemmi and Bulger when he in-fact did, facilitating obstruction of justice, perjury, filing false reports and lying to an FBI agent. A genuine RICO case, however, the United States Department of Justice has not indicted him for what-ever reason.As FBI agent: Connolly watched his life slip away in a Florida prison, FBI agents maintained their command center in Boston and spent millions on one of the most elaborate and expensive criminal manhunts ever mounted. All while, James “Whitey” Bulger and his lady, Catherine Greig, were living quietly in Santa Monica California.One would assume on the eve of the Bulger trial, it seemed a worthy endeavor to travel to Boston to interview some of the people who had been closest to him and the Winter Hill Gang back in the day when he was assuming control of the underworld and conniving with corrupted FBI agents: Connolly, Buckley, Ring, Callen, Morris, Newton.


2 thoughts on “Winter Hill Enterprise”

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Enlighten Yourself… “Where the willingness is great, the difficulties cannot be great. ” ~Niccolò Machiavelli, The Prince

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