•
William "Billy" Barnoski – Barnoski was a Winter Hill Gang
enforcer. He was convicted in 1984 on federal charges related to illegal sports betting. Upon his release from prison, Barnoski was given permission by the gang to take over the operations of
Lowell bookmaker John "Jackie" McDermott. After learning that McDermott had begun cooperating against him, Barnoski killed John McDermott and wounded his son, Peter McDermott, at their home on May 10, 1988. He was convicted of murder and attempted murder, and sentenced to life in prison on June 27, 1989. He died from MRSA and sepsis at a
Leominster hospital aged 74 on September 9, 2013. He was sent to federal prison for bank robbery in 1956, serving part of his sentence at
Alcatraz, before being released in 1965. Bulger became an enforcer for the South Boston crime boss
Donald Killeen, head of the
Killeen Gang. After Killeen was gunned down by the rival
Mullen Gang in 1972, Bulger was consolidated into the Winter Hill Gang. In 1979, Bulger and Flemmi were omitted from a federal horse race-fixing indictment which resulted in the imprisonment of Winter Hill Gang boss
Howard Winter, allowing the duo to take control of the gang. In December 1974, Callahan became the president and chief executive officer of World Jai Alai (WJA), a Florida-based sports betting enterprise which operated
jai alai frontons in
Miami,
Tampa,
Ocala, and
Fort Pierce. He recruited several Bostonians into WJA, including the corrupt retired FBI agent
H. Paul Rico, who he hired as head of security. Callahan was also a close associate of
John Martorano, who was living in South Florida as a fugitive, and acted as a gang conduit by ferrying money from George Kaufman in Boston to Martorano in Florida. With the assistance of his Boston associates, Callahan implemented a scheme which allowed the Winter Hill Gang and its leaders,
James Bulger and
Stephen Flemmi, to
skim over $1 million per year from WJA. •
Nicholas V. "Nick" Femia – Femia was an enforcer for
Joseph Barboza's East Boston Gang and a veteran of the 1960s Boston gang wars. In 1966, he was arrested by the Boston police along with two others after they were stopped while traveling in a car containing an
M1 Garand rifle, a .45 calibre pistol and a knife. Femia briefly served as a bodyguard for Winter Hill Gang leaders James Bulger and Stephen Flemmi. He was the younger brother of
Vincent Flemmi. Flemmi was affiliated with the
Patriarca crime family and the Winter Hill Gang. In 1979, Winter Hill Gang boss
Howard Winter and others were indicted in a federal horse race-fixing case. Due to the influence of Connolly and his FBI supervisor,
John Morris, Flemmi and Bulger were left out of the indictment and were able to assume leadership of the gang. •
Vincent James "Jimmy the Bear" Flemmi — The older brother of Stephen Flemmi, Vincent Flemmi was a hitman and
FBI informant. He was a fugitive for three years after escaping prison in 1975. Flemmi died of a drug overdose in
Norfolk State Prison on October 16, 1979. •
James P. "Jimmy" Flynn – Flynn was a Winter Hill Gang associate from Somerville. He was wrongfully implicated in the May 1982 double murder of Brian Halloran and Michael Donahue. James Bulger had committed the killings while wearing a brown wig which made him resemble Flynn, and the dying Halloran incorrectly identified Flynn as his shooter. Flynn was acquitted of murder charges in 1986. He became the transportation coordinator for
Teamsters Local 25, working in the film industry. In June 2000, Flynn's
Weymouth home was raided by federal agents, but he was not charged. Flynn died on September 12, 2022, at the age of 88. •
Edward Brian "Balloonhead" Halloran — Halloran was born in
Medford on July 23, 1940. He was a minor associate of the Winter Hill Gang and the
Patriarca crime family who operated as an enforcer and cocaine dealer. In the early hours of October 13, 1981, Halloran accompanied Patriarca mobster John Salemme to a meeting with George Pappas, a drug dealer who had defrauded a cocaine/marijuana ring jointly controlled by the Winter Hill Gang and Patriarca family, at the Four Seas Chinese restaurant in Boston's
Chinatown. During the meeting, Halloran fatally shot Pappas through the eye. Charged with first-degree murder and released on $50,000 bail, Halloran survived two attempted shootings by the Mafia before he began cooperating with the FBI in January 1982, requesting immunity and protection in return. The FBI initially moved him and his family to a home on
Cape Cod for security. On May 11, 1982, Bulger, along with an unidentified accomplice, killed Halloran in a drive-by shooting outside
Anthony's Pier 4 restaurant in South Boston. An acquaintance of Halloran, Michael Donahue, was also killed in the attack. •
John T. Hurley – Hurley was a minor associate of the
Charlestown and Winter Hill gangs. In 1966, he survived being shot in a barroom. In 1982, Hurley inadvertently tipped off gang boss James Bulger to the whereabouts of Brian Halloran, who had gone into hiding after becoming an FBI informant, resulting in Bulger killing Halloran hours later. •
George Kaufman – Kaufman was a senior member of the Winter Hill Gang. He served as the gang's liaison to the Patriarca family and to Boston's network of Jewish bookmakers. Kaufman owned a series of garages, including those on Marshall Street in
Somerville and Lancaster Street in Boston's
West End, which were used as Winter Hill Gang headquarters. The gang used Kaufman's
Brookline home to house a stockpile of weapons until the late 1980s, when the cache was moved the Stephen Flemmi's parents' home in South Boston. On January 10, 1995, Kaufman was indicted along with six other gangsters on federal racketeering, extortion and loansharking charges. He was a major drug trafficker who operated under the protection of the Winter Hill Gang. On May 29, 1978, LePere kidnapped Michael J. Romanelli, who worked for another major marijuana dealer, Donald J. Steinberg, after Romanelli used LePere's pier in
Plymouth to unload 30 tons of marijuana without LePere's permission. After being held for ransom at a
Marshfiled apartment for five days, Romanelli was released when LePere received $500,000 from Steinberg's organization. Beginning in 1979, He also bribed David P. Twomey, a federal prosecutor with the New England Organized Crime Strike Force, for information on investigations and pending indictments. Twomey was the lead prosecutor in the Strike Force's investigation into a drug ring headed by LePere, which imported marijuana from Colombia into Maine, Vermont, Rhode Island, New Hampshire, Massachusetts and South Carolina. A warning from Twomey allowed LePere to flee to upstate New York before he was indicted on drug importation charges on December 8, 1981. LePere remained at large until he was arrested by the
DEA near
Lake George at
Kattskill Bay, New York on November 2, 1984. He pleaded guilty in June 1985 to smuggling 145 tons of marijuana into the United States and became a government witness, providing information which led to the prosecution of Twomey on bribery charges. LePere was sentenced on July 18, 1985 to five years in federal prison. He also agreed to forfeit to the government $1.25 million in real estate and $1.6 million in cash. LePere was released in November 1987 after serving 30 months. He then relocated to Florida, where he died on January 30, 2021, aged 77. While imprisoned, Martorano was indicted in 1979 along with twenty other Winter Hill Gang members and associates on federal race-fixing charges relating to the fixing of horse races during the mid-1970s. He was convicted in 1980. Martorano later became a "
made" member and
capo in the
Patriarca crime family. In 1995, he was indicted along with the leaders of the Patriarca family and the Winter Hill Gang on federal racketeering charges. He also owned Triple-O's Lounge, a South Boston tavern that was used as a headquarters by Winter Hill Gang members. O'Neil was arrested on federal racketeering charges on November 17, 1999. He cooperated with the government, pleaded guilty to racketeering in October 2000, and was sentenced to a year in prison in September 2004. •
Charles G. "Charlie" Raso – Raso was a bookmaker originally partnered with Joe Notorangeli, who was killed by the Winter Hill Gang in 1973. He then began working with James Bulger, Steve Flemmi and John Martorano. He also laundered money for Martorano. •
James L. "Jimmy" Sims – Sims was a founding member of the Winter Hill Gang. He was involved in the gang's horse race-fixing scheme and went on the run in 1977 to avoid state charges before being captured in
Key West, Florida in 1982. Sims was convicted in the race fixing scheme in 1983, and disappeared following his release from
Walpole State Prison in 1987. He was among the original members of the Winter Hill Gang. Sperlinga was convicted in January 1978 and sentenced to nine-to-ten years in state prison. While on work release from prison on January 4, 1980, Sperlinga was shot and killed by drug dealer Daniel Moran as he played cards in a social club in
Magoun Square. Sperlinga had reportedly tried to keep Moran out of the neighborhood. Moran was convicted of first-degree murder and sentenced to life in prison. •
Howard Thomas "Howie" Winter – Winter was a founding member of the Winter Hill Gang, He died, aged 91, on November 12, 2020. •
Joseph "Joey Y" Yerardi – Yerardi was a
Newton bookmaker and loanshark. == List of murders committed by the Winter Hill Gang ==