Winter Hill Gang

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Winter Hill Gang
Founded1955;70 years ago (1955)
Founder James "Buddy" McLean
Founding location Somerville, Massachusetts, United States
Years active1955–2000
Territory Greater Boston and South Florida
EthnicityPredominantly Irish American, as well as Italian American
Membership (est.)30 (1975) [1]
ActivitiesRacketeering, loan sharking, assault, murder, bribery, fraud, theft, robbery, illegal gambling, drug trafficking, money laundering, corruption, extortion, prostitution, weapons trafficking
Allies
Rivals

The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts area. It was generally considered an Irish Mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, although some notable members, such as Stephen Flemmi and Johnny Martorano, are of Italian-American descent. [3]

Contents

The organization itself derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. [4] Amongst its members several have been notorious Boston gangsters, such as James "Buddy" McLean, James "Whitey" Bulger, Howie Winter, Joseph "Joe Mac" McDonald, Patrick Nee, Kevin Weeks and Stephen Flemmi. They were most influential from 1965, under the rule of McLean and Winter, to the 1979 takeover led by Bulger.

The Winter Hill Gang was given its name in the 1970s by journalists at the Boston Herald , but the name is hardly ever openly used as a reference to them. Winter Hill Gang members are alleged to have been involved with most typical organized-crime-related activities, but they are perhaps best known for fixing horse races in the northeastern United States and shipping weapons to the Provisional Irish Republican Army (IRA). [5] Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979. [6]

History

Irish Gang War

The Boston Irish Gang War started in 1961 and lasted until 1967. It was fought between the McLaughlin Gang of the Boston neighborhood of Charlestown, led by Bernie McLaughlin, and the Winter Hill Gang of Somerville, led by James "Buddy" McLean. [7]

The two gangs had co-existed in relative peace for a number of years until an incident at Salisbury Beach on Labor Day weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alexander Petricone, Jr. (who fled the Boston area during the war and became an actor under the name Alex Rocco). [8] McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital. [7] Bernie McLaughlin went to see "Buddy" McLean and demanded that he hand over the members of the gang who beat his brother. McLean refused. The McLaughlins took this refusal as an insult and attempted to wire a bomb to McLean's wife's car. In retaliation, McLean shot and killed McLaughlin coming out of the "Morning Glory" bar in Charlestown in October 1961. This was the start of Boston's Irish Gang War. [7]

In 1965, McLean was shot and killed by one of the last survivors of the McLaughlin Gang, Steve Hughes. Howie Winter then assumed control of the Winter Hill Gang. One of the surviving McLaughlin brothers, nicknamed "Punchy", was shot while waiting for a bus in the West Roxbury section of Boston. A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by hitman Frank Salemme. By the time the war finally ended, more than 60 men had been murdered throughout Boston and the surrounding area.

After the Irish Gang war, the Winter Hill Gang was reputed to be not only the top Irish Mob syndicate in the New England area, but New York City, as well. In the book Black Mass by Dick Lehr and Gerard O'Neill, the authors make the unsubstantiated claim that the Winter Hill Gang was far more feared and powerful than their rivals, the Boston branch of the Patriarca crime family run by the Angiulo brothers.

Winter era

DEA chart of the Winter Hill Gang structure circa 1975. Winter Hill Gang chart.jpg
DEA chart of the Winter Hill Gang structure circa 1975.

During the 1970s, the gang's most prominent members were Howie Winter, John Martorano, James J. Bulger, Stephen Flemmi, Joseph McDonald and James Sims. [7] The gangsters used the office of Marshall Motors, a large body shop on Marshall Street in Somerville, as their social club and headquarters. [9]

In March and April 1973, the Winter Hill Gang murdered Michael Milano, Al Plummer, William O'Brien, James Leary, and Joseph "Indian Joe" Notarangeli as they sought to eliminate a rival gang headed by Alfred "Indian Al" Notarangeli, [10] who had began extorting bookmakers who were under the protection of other criminal groups. [11] [12] After several failed attempts on his life, [13] Al Notarangeli was shot in the head and left in the trunk of his car by the Winter Hill Gang on February 22, 1974 at the request of the Patriarca family. [11] [14] On November 20, 1974, Paul "Paulie" McGonigle, the leader of the Mullen Gang which rivaled the Winter Hill Gang for control of rackets in South Boston, was shot and killed by the Winter Hill Gang in the back seat of a car. [11] [13] His body was buried at Tenean Beach in Dorchester. [15]

The Winter Hill Gang was quite proficient at murdering rival mobsters in order to take over their rackets. But once they gained control, they had no idea how to run them. They learned the lesson of their gang's disastrous foray into gambling after wiping out Notarangeli's crew. In what should have been a fabulously profitable illicit gambling enterprise, the gang lost it. As the years went by, Bulger and Flemmi lost interest in running any kind of gambling operation. They would eventually only provide protection for bookmakers, drug dealers and truck hijackers. By 1975, Howie Winter and John Martorano were going broke. Eventually they had to go to Patriarca family underboss Gennaro "Jerry" Angiulo to borrow money. To make the weekly payments, they began going into businesses with people they didn't know and couldn't trust. These activities included rigging horse races and drug trafficking. [7]

In 1975, the Winter Hill Gang was allegedly on the verge of a mob war with the Patriarca family in a dispute over the placement of vending machines around the Greater Boston area. [6] The Organized Crime Program of the Boston division of the Federal Bureau of Investigation (FBI) focused on the Patriarca family as their main priority, considering the Winter Hill Gang a lesser threat, [16] and recruited Bulger and Flemmi into the FBI's Top Echelon Informant program. [17] Bulger and Flemmi began providing information on the Mafia in exchange for protection from the FBI. [18]

It was the Winter Hill Gang's decision to involve outsiders with their business that led to their downfall. [7] In February 1979, 21 members and associates, including Winter, were indicted by federal prosecutors after being implicated by former business partners in connection with a million-dollar horse race-fixing scheme. [6] [18] Bulger's and Flemmi's status as confidential FBI informants kept them from being indicted. [6] [19] When Winter and the rest of the Somerville crew were all sent to prison, Bulger and Flemmi were able to assume control as the new leaders of the Winter Hill Gang. [7] [18]

Bulger era

FBI surveillance photograph of the former Winter Hill Gang hierarchy in the 1980s. Mob boss Whitey Bulger (right) and lieutenant Stephen Flemmi. FBI surveillance photograph of James J. Bulger (r.) and Stephen Flemmi (l.).jpg
FBI surveillance photograph of the former Winter Hill Gang hierarchy in the 1980s. Mob boss Whitey Bulger (right) and lieutenant Stephen Flemmi.

In 1979 and 1980, Bulger used Lancaster Foreign Motors, a parking garage in Boston's West End owned by Winter Hill Gang associate George Kaufman, as the gang's headquarters, where he openly met with and accepted payments from associates. [20] After putting the garage under surveillance for six months, the Massachusetts State Police were granted a warrant to plant covert listening devices on the premises in the summer of 1980. [21] Bulger's allies in the FBI alerted him to the police surveillance, [22] and he and Flemmi subsequently began operating from South Boston. [20] In November 1980, Bulger and Flemmi helped the FBI plant a bug in the headquarters of Jerry Angiulo in the North End. [18] Angiulo and a number of his associates were indicted in 1983 and later convicted, allowing the Winter Hill Gang to take over the rackets that had been controlled by the Patriarca family. [23]

During the 1980s, Bulger's associates consisted of Kevin Weeks, Kevin O'Neil, and Patrick Nee. By 1991, even as James J. Bulger's criminal career was winding down, he remained the undisputed mob boss. His criminal associate Kevin Weeks was not considered a threat, and neither were Jim Mulvey, even though he suspected Bulger of being an FBI informant, Billy Shea, John Shea, Tim Connolly, Pat Linskey, Eddie MacKenzie, Paul "Polecat" Moore or John Cherry. Boston journalist Howie Carr commented, "They hadn't really been gangsters so much as they'd been ex-boxers and bar-room brawlers who had become cocaine dealers." One problem that arose with the gang was that they enjoyed partaking in their own vices. Like their customers, they spent afternoons in the fall drinking beer and watching professional football on television, often doubling up wagers on late West Coast games as they desperately tried to break even and chased their losses. Despite the above unsubstantiated claims of the gang's apparent inability to successfully run organized crime rackets, Bulger generated well over $25 million in racketeering proceeds alone throughout his criminal career, according to paperwork filed in federal court. [7]

The Winter Hill Gang played a role in the Irish Republican Army's paramilitary actions in the late 20th century. In his novel, A Criminal and an Irishman, Patrick Nee detailed the gang's involvement with the IRA. He said that Bulger "loved being associated with the IRA and the cause of Irish Freedom". [24] He went on to say that Bulger's association with the IRA gave him a sense of legitimacy. Nee played an active role in raising funds and smuggling weapons to the IRA. In September of 1984, the Valhalla, a fishing boat, left Boston harbor loaded with weapons. [24] The vessel was seized by two Irish Naval Service ships upon arriving in Ireland having been sold out by an Irish informant. The Winter Hill Gang also had a plot spoiled by a local fisherman John McIntyre who they had partnered with but who went to the police after hearing word of a gun-running mission. [25] The authorities attempted to use McIntyre as an informant against Whitey Bulger. However, Whitey Bulger received information from FBI agent John Connolly that the fisherman had gone to the police. Connolly provided McIntyre's whereabouts and Whitey Bulger along with his right-hand man Stephen Flemmi tortured and killed him. [25]

FBI informants

In 1998, during a trial for racketeering and fixing horse races, Steve Flemmi and Whitey Bulger were revealed under disclosure to be FBI informants. Steve Flemmi and Whitey Bulger were implicated in many unlawful activities, including murder, but were never brought to justice due to their FBI handlers diverting their guilt onto others in the gang or various other gangs of the time. They were first handled by Special Agent H. Paul Rico and then later by SA John "Zip" Connolly. In addition to providing details on other gangs, Flemmi and Bulger relayed information on fellow members of the Winter Hill Gang to the FBI. When they had nothing to report, they would make up information to ensure that they were seen to be of high value to the agency. [26]

Historical leadership

Leaders

Notable associates

List of murders committed by the Winter Hill Gang

NameDateReason
Michael MilanoMarch 8, 1973Bartender Milano was shot by John Martorano after he was mistaken for Alfred "Indian Al" Notarangeli, a rival gang leader. [29]
Albert "Bud" PlummerMarch 19, 1973Plummer, a member of Notarangeli's gang, was killed by Martorano using a machine gun while he was driving in the North End during an attempt to kill Notarangeli. [29] [30]
William O'BrienMarch 24, 1973Notarangeli gang member O'Brien was shot as he drove in South Boston. [29] [31]
James LearyApril 3, 1973Leary was a member of the Notarangeli gang. [31] He was shot in Miami, Florida. [11]
Joseph "Indian Joe" NotorangeliApril 18, 1973Notorangeli was the brother of Al Notorangeli. [32] He was shot at a payphone in Boston. [11] [33]
James "Spike" O'Toole December 1, 1973Former Charlestown Mob associate O'Brien was shot in Boston after he had wounded the brother of Stephen Flemmi in a shooting. [29] [31]
Alfred "Indian Al" NotarangeliFebruary 21, 1974The leader of a rival gang, Notarangeli was shot and killed by Martorano after several failed attempts. [14] [29] Notarangeli's body was left in the trunk of his car. [11]
James SousaOctober 1974Sousa was killed by Whitey Bulger and Flemmi after he was arrested and charged in connection with a botched robbery of a dentist in which he participated with Bulger. [32] Bulger was concerned that Sousa may implicate him in the crime. [29] Sousa's body was buried and has never been recovered. [11]
Paul "Paulie" McGonagle November 20, 197436-year-old McGonagle was the leader of the Mullen Gang, a rival gang in South Boston. [31] He wash shot by Bulger after being lured into a car in the Lower End. [33] McGonagle was buried at Tenean Beach in Dorchester, and his body was found in September 2000. [34]
Edward George Connors June 12, 1975Connors was shot by Bulger and Flemmi after being lured to a gas station because he had witnessed O'Toole's murder and the gang feared he would inform law enforcement. [29] [30] [32]
Thomas "Tommy" KingNovember 5, 1975Mullen Gang member King was lured into a car and shot by Martorano on the orders of Bulger days after he was involved in a bar fight with Bulger. [35] His body was buried near the Neponset River in Quincy. [36] King's remains were unearthed in September 2000. [37]
Francis "Buddy" LeonardNovember 6, 1975Leonard, a friend of King, was killed to divert attention from King's disappearance. He was found shot to death in King's car. [38] Bulger spread the rumor that King had killed Leonard. [29]
Richard Castucci December 29, 1976 Patriarca crime family member and FBI informant Castucci was killed after FBI agent John Connolly told Bulger that Castucci was an informant. Castucci had told the FBI the whereabouts of two fugitive Winter Hill Gang members. [38] He was shot and left in the trunk of his car. [11]
Roger Wheeler May 27, 198155-year-old Wheeler was the owner of World Jai Alai in Miami. He was shot by Martorano at a country club in Tulsa, Oklahoma after he discovered that the gang were skimming money from his business. [29]
Debra "Debbi" DavisSeptember 17, 1981Davis, a 26-year-old girlfriend of Flemmi, was strangled by Flemmi after she tried to end their relationship and was deemed a threat to the gang. [39] She was buried under the Neponset River Bridge in Quincy. [40] Davis' body was recovered in October 2000. [41]
Michael Donahue and Edward Brian "Balloonhead" HalloranMay 11, 1982Bulger killed Halloran and Donahue in a drive-by shooting using a carbine rifle in South Boston. [42] FBI informant Halloran was targeted after Bulger was alerted by FBI agent Connolly that Halloran had implicated Bulger in two murders, while Donahue, a neighbor of Halloran, was killed because he simply happened to be at the scene. [43]
John B. CallahanAugust 2, 1982Callahan was a former president of World Jai Alai. He was shot by Martorano on the orders of Bulger after Bulger became concerned that Callahan might implicate him in Wheeler's murder. [29] Callahan's body was found in the trunk of a car at Miami International Airport. [32]
Arthur "Bucky" BarrettNovember 30, 198346-year-old jewel thief and bank robber Barrett was one of six men who stole $1.5 million from a bank in Medford in 1980. [44] Kevin Weeks lured Barrett to a house in South Boston, where Bulger tortured Barrett until he revealed the location of the cash he had hidden. [29] Bulger then shot him. [45] Barrett was buried in the basement of the house before his remains and those of two others were reburied at a site in Dorchester in October 1985. [46] His remains were retrieved in January 2000. [32]
John McIntyreNovember 30, 198432-year-old fisherman and FBI informant McIntyre was shot by Bulger six weeks after providing the FBI with information regarding Bulger and Flemmi's gunrunning and drug smuggling operations. [29] He had implicated the pair in a plot to ship guns to the IRA. [32] FBI agent Connolly tipped Bulger off about McIntyre's role as an informant. McIntyre's body was initially buried in the basement of a South Boston home before being exhumed along with two others and reburied in Dorchester in October 1985. [46] His remains were found in January 2000. [47]
Deborah HusseyJanuary 198526-year-old Hussey was the stepdaughter of Flemmi and daughter of Flemmi's girlfriend, Marion Hussey. She was lured to a house in South Boston and strangled by Bulger and Flemmi because she was using drugs and drawing attention to the gang. [29] Hussey was first buried in the basement of the house. [45] In October 1985, her body was reburied in Dorchester with two others. [46] Hussey's remains were found in January 2000. [32]

See also

References

  1. ↑ Boston Gang Wars — The Gangs Matt Connolly, Medium (January 1, 2022) Archived February 1, 2025, at archive.today
  2. ↑ Whitey Bulger & The Detroit Mafia: Boston's Winter Hill Gang Came To Motown To Fix Horse Races Scott Burnstein, The Gangster Report (November 2, 2018) Archived October 19, 2021, at the Wayback Machine
  3. ↑ "Hitman : The Untold Story Of Johnny Martorano : Whitey Bulger's Enforcer And The Most Feared Gangster In The Underworld by Howie Carr". Johnston Public Library. Retrieved July 18, 2023.
  4. ↑ "Winter Hill Gang (FBI internal memo)". September 12, 1987. Retrieved May 16, 2021– via archive.org.
  5. ↑ Finley, Bill (July 16, 2013). "The reverend's deal with the devil; Eddie Donnally crossed Boston mobsters and lived to tell about it". ESPN.com. Retrieved October 4, 2013.
  6. 1 2 3 4 Murphy, Shelley (July 22, 1998). "Howie Winter never saw Bulger coming". The Boston Globe . Archived from the original on February 14, 2003. Retrieved September 3, 2023.
  7. 1 2 3 4 5 6 7 8 Carr, Howie (2006). The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century. Hachette Book Group. ISBN   9780446506144 . Retrieved September 5, 2021.
  8. ↑ Teresa, Vincent. My Life in the Mafia.
  9. ↑ Somerville’s current polyamorous people are much, much nicer than the Winter Hill Gang Kevin Cullen, The Boston Globe (March 28, 2023) Archived March 29, 2023, at archive.today
  10. ↑ Winter Hill Gang Leader Pleads Guilty Drug Enforcement Administration (October 14, 2003) Archived July 15, 2021, at the Wayback Machine
  11. 1 2 3 4 5 6 7 8 Caught In Santa Monica, Mobster Appears Addled Tampa Bay Times (June 24, 2011) Archived February 17, 2025, at archive.today
  12. ↑ James ‘Whitey’ Bulger linked to 11 murders CNN (August 12, 2013) Archived February 17, 2025, at archive.today
  13. 1 2 A Look At The 19 Murder Victims In Bulger Trial CBS News (August 12, 2013) Archived February 17, 2025(Date mismatch), at archive.today
  14. 1 2 Ex-hit man John Martorano ties Whitey Bulger to murder as federal trial continues in Boston Boston.com (June 17, 2013) Archived February 17, 2025, at archive.today
  15. ↑ Paul 'Paulie' McGonagle Boston 25 News (June 11, 2013) Archived February 17, 2025, at archive.today
  16. ↑ Emily McIntyre and Christopher McIntyre Casetext (September 5, 2006) Archived February 4, 2025, at archive.today
  17. ↑ Assets and Liabilities Patrick Radden Keefe, The New Yorker (September 14, 2025) Archived February 18, 2025, at archive.today
  18. 1 2 3 4 Key Events In The Life Of James 'Whitey' Bulger CBS News (August 12, 2013) Archived February 18, 2025, at archive.today
  19. ↑ The Whitey Bulger Trial: A Six-Point Primer Madison Gray, Time (June 4, 2013) Archived February 18, 2025(Date mismatch), at archive.today
  20. 1 2 Whitey Bulger and the Lancaster Street Garage The West End Museum Archived February 17, 2025, at archive.today
  21. ↑ Whitey eludes snares set by troopers, DEA Christine Chinlund, Dick Lehr and Kevin Cullen, The Boston Globe (September 18, 2015) Archived February 18, 2025, at archive.today
  22. ↑ James Whitey Bulger, 9 years later Bob Ward, Boston 25 News (June 23, 2020) Archived February 17, 2025, at archive.today
  23. ↑ James ‘Whitey’ Bulger: How one of America’s most wanted turned FBI informer Ryle Dwyer, Irish Examiner (November 1, 2018) Archived February 18, 2025, at archive.today
  24. 1 2 Nee, Patrick (2010). A Criminal and an Irishman. Steerforth Press.
  25. 1 2 "John McIntyre". WCVB. August 9, 2011. Retrieved April 1, 2022.
  26. ↑ Carr, Howie (2011). Hitman: The Untold Story of Johnny Martorano: Whitey Bulger's Enforcer and the Most Feared Gangster in the Underworld. Tom Doherty Associates. ISBN   9780765365316 . Retrieved September 5, 2021.
  27. ↑ "McLean vs the McLaughlins Feud". Life . February 24, 1967. p. 26-27 – via Google Books.
  28. ↑ Weeks, Kevin; Karas, Phyllis (2006). Brutal: the untold story of my life inside Whitey Bulger's Irish mob. ReganBooks. ISBN   9780061122699 . Retrieved September 6, 2021.
  29. 1 2 3 4 5 6 7 8 9 10 11 12 13 A look at the 19 murder victims in Bulger trial The Patriot Ledger (August 12, 2023) Archived November 30, 2022, at the Wayback Machine
  30. 1 2 James (Whitey) Bulger’s Alleged Victims The New York Times Archived August 11, 2022, at the Wayback Machine
  31. 1 2 3 4 Whitey Bulger’s alleged hit list Victoria K. Kim, Los Angeles Times (June 24, 2011) Archived November 12, 2020, at the Wayback Machine
  32. 1 2 3 4 5 6 7 Alleged mob victims The Boston Globe (September 29, 2000) Archived February 2, 2025, at archive.today
  33. 1 2 Carr: If you”re a gangster, it helps to be two-faced Howie Carr, Boston Herald (November 17, 2018) Archived February 17, 2025, at archive.today
  34. ↑ Bodies of 5 Boston Mob Victims Found Los Angeles Times (September 23, 2000) Archived February 2, 2025, at the Wayback Machine
  35. ↑ Police unearth Bulger's secrets Cape Cod Times (September 23, 2000) Archived February 2, 2025, at the Wayback Machine
  36. ↑ Feds dig up Boston mob victim, seek another United Press International (September 22, 2000) Archived February 2, 2025, at archive.today
  37. ↑ 'Whitey' Bulger: 'Tip Your Hat to Tommy' as He Passed Tommy King's Highway Grave Michele McPhee, ABC News (June 25, 2013) Archived 2013-06-26 at the Wayback Machine
  38. 1 2 Whitey Bulger trial: Widow of alleged victim of reputed mob boss testifies CBS News (June 25, 2013) Archived February 2, 2025, at the Wayback Machine
  39. ↑ Family of mobster’s murdered girlfriend awarded $33.5 million – but gangsters are unlikely to pay John P. Kelly, The Patriot Ledger (September 18, 2009) Archived September 26, 2022, at the Wayback Machine
  40. ↑ A Closer Look at Alleged Bulger Victim Debra Davis NECN (February 28, 2014) Archived August 10, 2020, at the Wayback Machine
  41. ↑ Family greets discovery of Debra Davis' body with relief, sadness Lisa Lipman, South Coast Today (October 20, 2000) Archived February 1, 2025, at the Wayback Machine
  42. ↑ Former Protégé of Bulger Recounts 1982 Double Murder, and Its Code Words Richard A. Oppel Jr., The New York Times (July 8, 2013) Archived July 10, 2013, at the Wayback Machine
  43. ↑ Ex-partner: 'Bulger just kept shooting' in 1982 homicides Deborah Feyerick, CNN (July 8, 2013) Archived July 9, 2013, at the Wayback Machine
  44. ↑ Arthur "Bucky" Barrett Boston 25 (June 11, 2013) Archived February 2, 2025, at archive.today
  45. 1 2 Boston home was death house for 'Whitey' Bulger victims: gangster Scott Malone, Reuters (June 22, 2013) Archived February 2, 2025, at archive.today
  46. 1 2 3 At ‘Whitey’ Bulger trial, forensic expert describes remains found in secret graveyard in Dorchester in 2000 Shelley Murphy and Milton J. Valencia, Boston.com (July 10, 2013) Archived February 4, 2025, at archive.today
  47. ↑ John McIntyre Boston 25 (June 11, 2013) Archived February 1, 2025, at archive.today
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