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The “Back Story” to the Boston Mafia:
The Winter Hill Gang.
Although the Winter Hill Gang was not Italian Organized Crime and therefore does not get mention on these pages their existence and how they operated had a definite influence on the New England Organized Crime family, so we've dedicated a page to their story. We've called it the Back Story because the focus of this site is the Italian Organized Crime Family. We've consolidated their history down to events which pertain to the Boston Mafia and the players who were involved. The Winter Hill gang was a loose confederation of Boston, Massachusetts area organized crime figures, predominantly Irish-American with a small Italian-American faction. The name is derived from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its boss, James J. “Whitey” Bulger and his associate Stephen "The Rifleman" Flemmi took over the gang in 1979 and set up headquarters at the Lancaster Street Garage in Boston near the Boston Garden in the city's North End. This group had a very large impact on the Boston Mafia.
The Players
James Joseph "Whitey" Bulger, Jr., born in 1929 is a wanted fugitive. He is the older brother of William Michael Bulger, a former President of the Massachusetts State Senate and the University of Massachusetts. Beginning in 1975, Bulger was a top echelon informant for the FBI who was recruited by John "Zip" Connolly and provided a great deal of information about his enemies and those that opposed him. Bulger became the 458th person added to the FBI Ten Most Wanted Fugitives list and is wanted for RICO, murder, conspiracy to commit murder, extortion, conspiracy to commit extortion, money laundering, conspiracy to commit money laundering and narcotics distribution.

James "Whitey" Bulger
Stephen Joseph "The Rifleman" Flemmi, born in 1935, is an Italian-American mobster and close associate of Winter Hill Gang boss James J. Bulger. In 1965, FBI Special Agent H. Paul Rico recruited Flemmi as an informant, just what the FBI needed to obtain intelligence about the Patriarca crime family. Flemmi was a top echelon informant for the FBI and provided a great deal of intelligence about the inner workings of the Patriarca crime family. Flemmi's own criminal activities proved to be his undoing and he was prosecuted under RICO and sentenced to a long term in Federal prison.

Stephen"The Rifleman" Flemmi
Kevin "Two" Weeks, born in 1956, is a former mobster of Irish-American descent and a longtime friend and confidant to James J. Bulger After his arrest and imprisonment in 1999, he became a cooperating witness. His testimony is viewed as contributing to the convictions of FBI agent John Connolly and mobster Stephen Flemmi. Since his release from prison, he has written a bestselling true crime memoir, Brutal: My Life in Whitey Bulger's Irish Mob.
John Vincent Martorano is a former hitman for the Winter Hill Gang, who has admitted to 20 gang-related killings. He is the son of Patriarca crime family associate Luigi Martorano. Arrested in 1995, Martorano agreed to a plea bargain deal in 1999. In return for confessing his murders, Martorano received a reduced prison sentence of 14 years. In 2007, he was released from prison and given $20,000 to start a new life. On January 15, 2008, Martorano appeared on the CBS News television program 60 Minutes.

John Martorano
John J. "Zip" Connolly Jr. is a former FBI agent, currently incarcerated in a federal penitentiary for racketeering and obstruction of justice convictions stemming from his relationship with Whitey Bulger, Steve Flemmi, and the Winter Hill Gang. He is the brother-in-law of Arthur Gianelli who is married to Mary Ann Moore, the sister of Connolly's wife Elizabeth.

John "Zip" Connolly
Harold Paul Rico, born in 1925, died in 2004, was an FBI agent. Indicted for murder in 2003, he played a significant role in the 1968 framing of four men for murder, unjustly imprisoning them for decades. Rico was the son of a Spanish-American father and an Irish-American mother. He joined the FBI in the 1950's and worked in the Boston area and used members of the Winter Hill Gang as informants.

Harold Paul Rico
The Unraveling of the Winter Hill Gang
John Martorano 60 Minutes Interview
John Martorano Court Testimony
The Mafia “Back Story” in Boston.
In 1967, Joe “The Animal” Barboza, who along with his crew allied with Bulger and Flemmi during the early 1960’s gang war, became a cooperating witness for the FBI and disappeared into the Witness Protection Program. Flemmi and Frank Salemme arranged the car bombing of Barboza's lawyer, who was suspected of persuading his client to testify. He was severely injured, but survived. Flemmi and Salemme fled Boston as fugitives from justice until Salemme was arrested in New York City in 1972, Flemmi then fled to Montreal, Quebec.
FBI Agent Paul Rico watched as Joe Barboza testified in court against four men they both knew to be innocent of the 1965 murder of Edward “Teddy” Deegan.: Henry Tameleo Peter Limone, Joe Salvati and Louis Greco. Tameleo died in prison as did Greco. Salvati was released in 1997, and Limone in 2001. Barboza allegedly said that the Patriarca crime family had "screwed me and now I’m going to screw as many of them as possible."
In 1976, Weeks became a bouncer at a popular neighborhood bar, "Triple O's". This was a frequent hangout of the Winter Hill Gang and where he first met Bulger and Flemmi. Beginning in 1978, Weeks began working for Bulger part-time. Bulger genuinely liked him and decided to bring him into the organization.
In 1979 Bulger and Flemmi took over leadership of the Winter Hill gang and used their status as informants to eliminate their competition. The information they supplied to the FBI was responsible for the imprisonment of several Bulger associates but the main victim of their relationship with the federal government was the Italian-American Patriarca crime family, which was based in the North End of Boston and in Federal Hill, Providence, R.I.
Beginning in the early 1980s Bulger, Weeks, and Flemmi got involved in the illegal narcotics trade. They limited their associates to cocaine, hashish, and marijuana and did not want any other drugs on the streets of South Boston. A carefully chosen crew of prizefighters under John "Red" Shea handled most of the work of the drug business. Dealers of heroin and PCP were beaten up and driven out of the neighborhood.
In 1982, just four years after beginning to work as part of the Winter Hill Gang, Weeks left his legitimate jobs and became a full-time mobster.
In the late 1980s, a joint task force of the DEA, the Boston Police Department, and the Massachusetts State Police set out to bring the Winter Hill Gang down. In 1990, "Red" Shea and his entire crew was all rounded up and imprisoned. Shea and his associates refused to implicate their bosses. After the arrests, the gang returned to more conventional crimes.
Flemmi was a go-between between the Winter Hill Gang and the Mafia. Flemmi, who was full-blooded Italian, was considered a stand up guy by La Cosa Nostra and was offered the privilege of becoming a made man. Flemmi politely declined the offer and stayed with the Winter Hill Gang. Bulger and Flemmi took out a $200,000 loan from Anguilo and when Anguilo asked them about repayment, Bulger and Flemmi stalled him. Anguilo was infuriated and it appeared that a serious gang war was on the horizon; however, Flemmi had already described the layout of Anguilo's headquarters to the FBI who planted a bug in the building.
After the 1986 RICO indictment of under boss Gennaro Angiulo and his associates, largely due to the bug planted by the FBI,who were based in Boston, the Patriarca family's Boston operations were in shambles. Bulger and Flemmi stepped in to take control of organized crime in the Boston area.
Bulger's paranoid fear of wiretaps coupled with the corruption within the FBI and Mass. State Police continually thwarted State and Federal agencies in their attempts to build cases against Bulger and his inner circle. FBI agent John Connolly and Lieutenant Richard J. Schneiderhan of the Massachusetts State Police were highly valued assets to the gang.
In 1994, Bulger and Flemmi were informed that several imprisoned 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.
Flemmi chose to remain and was swiftly arrested and incarcerated at the Plymouth County House of Correction. Stephen believed he had protection, but not immunity. As time passed it became clear to Flemmi that no one was going to bail him out. He planned to prove through his testimony and that of others that he had indeed had protection from the FBI. Flemmi’s problem was he had no immunity and therefore could not admit to killings he hadn't been charged with. To many questions about the murders Flemmi was involved in, he plead the Fifth Amendment.
In 1999, Weeks and other Winter Hill associates were arrested in South Boston by agents of the DEA and the Mass. State Police. He was presented with a 29-count indictment under RICO and at first refused but later agreed to cooperate. He led authorities to six different bodies buried by the Winter Hill Gang, implicated Bulger in the murder of Edward Brian Halloran, as well as agreeing to testify against Stephen Flemmi, Special Agent Connolly, and Whitey Bulger. He was then sentenced to five years in federal prison.
State police and other federal officers had been trying to imprison Whitey Bulger for years, but somehow Bulger always avoided getting caught. As the FBI handler for Bulger and Flemmi, Connolly had been protecting them from prosecution by feeding him information about possible attempts to catch them.
Connolly was indicted on December 22, 1999 on charges of alerting Bulger and Flemmi to investigations, falsifying FBI reports to cover their crimes, and accepting bribes. In 2000, he was charged with additional racketeering related offenses. He was convicted on the racketeering charges in 2002 and sentenced to 10 years in prison.
In 2003 the U.S. House Judiciary Committee hearings looked into the Deegan killing and attorneys representing the families of Greco, Tameleo, Salvati and Limone filed suit. The two survivors and the estates of the deceased were awarded $101.7 million by U.S. District Judge Nancy Gertner in Boston on July 26, 2007.
In 2005, Connolly was indicted on murder and conspiracy to commit murder charges in the 1982 slaying of John B. Callahan. He stood trial in 2008 in Miami. Callahan was murdered by John Martorano who shot Callahan and left his body in the trunk of his Cadillac in a parking lot at Miami International Airport. Prosecutors alleged that Callahan was killed on the orders of James "Whitey" Bulger and Stephen Flemmi after Connolly told them that the FBI was investigating his ties to the Winter Hill Gang in their on going investigation into the death of World Jai Alai owner Roger Wheeler. Wheeler had also been killed by Martorano in Tulsa, Oklahoma in May 1981.
During the trial, Bulger associates Stephen Flemmi, Kevin Weeks and John Martorano testified for the prosecution detailing Connolly's ties to Bulger and Flemmi. Flemmi testified that Connolly warned them that the FBI wanted to question Callahan in the death of Wheeler telling them that Callahan "wouldn't hold up" and would probably implicate them.
Also testifying against Connolly was his former FBI boss, John Morris, who admitted that he accepted $7,000 in bribes from Bulger and Flemmi. He stated he began leaking information to them after Connolly delivered a case of wine and an envelope stuffed with $1000 cash from the pair.
Testifying for Connolly was Former US Attorney and current US District Senior Judge Edward F. Harrington who testified that Connolly was a star agent who was credited with using informants to help destroy the New England Mafia.
On November 6, 2008, a jury convicted Connolly of second-degree murder. According to the prosecutors, Connolly faced a possible sentence of 30 years to life in prison. On January 15, 2009, Connolly was sentenced to 40 years in prison the judge accepted the prosecutors' argument that Connolly abused his badge and deserved more than the 30-year minimum. The sentence will run consecutively with his 10-year sentence for racketeering, meaning that Connolly will spend the rest of his life in prison.
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