# Winter Hill Gang

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, were of Italian-American descent. The organization itself derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. The Winter Hill Gang was given its name in the 1970s by journalists at the Boston Herald.
The Winter Hill Gang was involved with most typical organized crime-related activities, including drug trafficking, gambling, and loan sharking, as well as fixing horse races throughout the northeastern United States, and shipping weapons to the Provisional Irish Republican Army (IRA). Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.
The Winter Hill Gang was the second most powerful criminal organization in New England, behind only the Patriarca crime family of Providence, Rhode Island. 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.

## History
### The Irish Gang Wars

The Winter Hill Gang was founded in 1961 by James "Buddy" McLean and Howie Winter, who were partners in a trucking company, when they became involved in illegal gambling, numbers running, bookmaking and loansharking in the Winter Hill neighborhood of Somerville, Massachusetts, a northwestern suburb of Boston. The Winter Hill Gang co-existed in relative peace with the McLaughlin Gang from the Boston neighborhood of Charlestown, led by Bernie, Georgie and Edward "Punchy" McLaughlin, 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 "Bobo" Petricone, Jr. McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital. Bernie McLaughlin went to see 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 Bernie McLaughlin coming out of the "Morning Glory" bar in Charlestown on October 31, 1961. This was the start of Boston's first Irish Gang War. McLean and Petricone, his alleged getaway driver, were arrested and charged with McLaughlin's murder but, as none of the numerous witnesses to the killing were willing to testify, they were released. Petricone fled the Boston area during the war and became an actor under the name Alex Rocco.
Although the McLaughlin brothers had a larger and more well-established gang, the Winter Hill Gang proved more dynamic and resourceful, recruiting killers such as Stephen "the Rifleman" Flemmi, Francis "Cadillac Frank" Salemme, and Joseph "the Animal" Barboza. Their rivals, meanwhile, suffered another significant setback when Georgie McLaughlin was sent to prison for life after shooting and killing a bank teller during an argument at a christening in an incident unrelated to the gang war.
The Winter Hill Gang made their first attempt on the life of the remaining brother, "Punchy" McLaughlin, after being tipped off that he was in the Hotel Beaconsfield, shotgunning him at point-blank range when he entered a car and blowing his jaw off. He survived after being rushed to the Beth Israel Hospital. In the second attempt, McLaughlin was ambushed by Winter, who was armed with a scoped .308 Winchester rifle, along with McLean, Flemmi and Salemme, who each carried a machine gun, as he arrived at a girlfriend's house in Weston. Winter blew McLaughlin's hand off with a rifle shot, but McLaughlin was able to flee and escaped after a car chase along Route 128. The Winter Hill Gang finally succeeded in killing McLaughlin when they shot him while he waited for a bus in the West Roxbury section of Boston on October 20, 1965. The one-handed McLaughlin was carrying a pistol in a satchel but was unable to draw the gun quickly enough to save himself.
Eleven days later, on October 31, 1965, McLean was shot and killed by one of the last survivors of the McLaughlin Gang, Steve Hughes, as he exited the 318 Club in Winter Hill. Winter then assumed control of the Winter Hill Gang. A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by Salemme. Connie Hughes was ambushed on the Northeast Expressway after leaving an afterhours club on May 25, 1966, and Stevie Hughes was killed along with an associate in a drive-by shooting on Route 114 in Middleton on September 23, 1966. The murders of the Hughes brothers marked the conclusion of the first Irish Gang War, with the Winter Hill Gang victorious despite the death of McLean. By the time the war finally ended, more than 60 men had been murdered throughout Boston and the surrounding area. Irish gang killings had become so prevalent in Boston that the obituaries sections in newspapers were jokingly referred to as "the Irish sports pages".
The second Irish Gang War in Boston began in the mid-1960s and was contested between the Mullen Gang and the Killeen Gang. Unlike the Winter Hill and McLaughlin gangs, which were city-wide organizations, the Mullens and Killeens were confined to South Boston and their feud essentially amounted to a local turf war. The Mullens were a loose-knit street gang with around 60 members, while their rivals were a smaller but more organized group led by the Killeen brothers, Donnie, Kenny and Eddie. The younger Mullens, whose ranks included many Vietnam War veterans, began encroaching on the territory of the Killeens, who had been the dominant gang in South Boston for two decades.
The Mullen–Killeen feud escalated significantly after an incident in 1969 in which Kenny Killeen bit off the nose of Mullen Gang member Mickey Dwyer in a bar fight at the Transit Café. Afterwards, a murder attempt was made on Mullen leader Patrick "Pat" Nee, whose gang retaliated by killing Killeen enforcer Billy O'Sullivan on March 28, 1971. The gang war nominally ended when Killeen leader Donald Killeen was gunned down outside his home in Framingham on May 13, 1972. Killeen's death left James "Whitey" Bulger in charge of the gang. Outnumbered, the Killeens agreed to negotiate with the Mullens, and a meeting between the gangs, which was mediated by Winter, was held at Chandler's bar in Boston's South End. The Mullens and Killeens agreed to cease hostilities and consolidate under the leadership of Winter.

### The Indian War

During the 1970s, the Winter Hill Gang's most prominent members were Winter, Flemmi, Bulger, John "the Executioner" Martorano, Joseph "Joe Mac" McDonald, and James "Jimmy" Sims. The gangsters used the office of Marshall Motors, a large body shop on Marshall Street in Somerville, as their social club and headquarters. Having emerged from the gang wars as the preeminent Irish-American crime group in Boston, the Winter Hill Gang controlled the city's Irish mob rackets under the strict supervision of the Patriarca crime family of Providence, Rhode Island. The Winter Hill Gang entered into an alliance with the family when Patriarca underboss Gennaro "Gerry" Angiulo enlisted the gang for assistance in a war against the Somerville-based Notarangeli gang, headed by Alfred "Indian Al" Notarangeli.
Notarangeli's gang had began extorting bookmakers who were under the protection of the Patriarca family, and while on furlough from prison in 1972, Notarangeli murdered one of Angiulo's bookies, Paulie Folino. The Winter Hill Gang began exterminating members of the Notarangeli gang. Explaining how the Winter Hill Gang differed from the Patriarca family in their methods of killing, Flemmi described the Winter Hill Gang as "hunters" who tracked down their targets, while the Mafia would wait, possibly for years, for their intended victim to show up on Hanover Street to kill them.
On March 8, 1973, Michael Milano, a bartender, was machine gunned to death in the Brighton neighborhood of Boston after Martorano mistook him for Notarangeli. Milano's friend, Louis Lapiana, and Lapiana's girlfriend, Dianne Sussman, were also wounded in the shooting. The Winter Hill Gang made another attempt to kill Notarangeli on March 19, 1973, when the car in which he was traveling was fired upon by Martorano and Winter in Boston's North End. Notarangeli survived unharmed. Two of his associates, Frank Capizzi and Hugh "Sonny" Shields, were injured. Notarangeli's driver, Albert "Bud" Plummer, died from his wounds, on March 23, 1973.
On March 24, 1973, William "Billy" O'Brien was killed when Martorano strafed his car with machine gun fire on Morrissey Boulevard in an attempt to murder another Notarangeli gang member, Ralph DeMasi, who survived being shot eight times. Another of Notarangeli's associates, James Leary, was shot dead while in hiding in Fort Lauderdale, Florida, on April 3, 1973. On April 18, 1973, Joseph "Indian Joe" Notorangeli, the brother of Al Notorangeli, was shot and killed by Martorano in a restaurant in Medford Square.
After fleeing to the West Coast, Notarangeli returned to Boston in late 1973 in an attempt to make peace with Angiulo. Notarangeli paid $50,000 to Angiulio, who shared the money with the Winter Hill Gang. On February 22, 1974, Notarangeli was shot in the head by Martorano and left in the trunk of his car.

### Infighting and leadership change

Following the merger of the Mullen and Killeen gangs into the Winter Hill Gang, several former Mullen members resented the amalgamation and continued to seek revenge against their former Killeen rivals. Winter sanctioned the murders of any members who were deemed subversive. Paul "Paulie" McGonagle, who sought retaliation against former Killeen Gang member Bulger for the killing of his brother and who rivaled Bulger for control of rackets in South Boston, was murdered on November 20, 1974. His body was buried at Tenean Beach in Dorchester.
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, Winter and Martorano were going broke. Eventually they had to go to 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.
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. 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, and recruited Bulger and Flemmi into the FBI's Top Echelon Informant program. Bulger and Flemmi began providing information on the Mafia in exchange for protection from the FBI.
The Winter Hill Gang became involved in a horse race-fixing scheme when Winter and Martorano partnered with Anthony "Fat Tony" Ciulla, a hustler from the North End of Boston, and his associate, Billy Barnowski, beginning in 1974. The gangsters would successfully place large wagers with bookmakers throughout the country on unfancied race horses after swaying betting odds in their favor by bribing and threatening jockeys and doping horses. The Winter Hill Gang made millions of dollars by fixing races along the East Coast, and became the second most influential crime group in New England, behind only the Patriarca family. The gang partnered with mobsters from the Genovese, Bruno and Tocco–Zerilli crime families in infiltrating race courses in Massachusetts, New York, Pennsylvania, Maryland, and Michigan.
It was the Winter Hill Gang's decision to involve outsiders with their business that led to their downfall. After being arrested, Ciulla began cooperating with federal authorities and informing on the gang. 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. Bulger's and Flemmi's status as confidential FBI informants kept them from being indicted. 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.

### Bulger era

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. 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. Bulger's allies in the FBI alerted him to the police surveillance, and he and Flemmi subsequently began operating from South Boston. In November 1980, Bulger and Flemmi helped the FBI plant a bug in the headquarters of Jerry Angiulo in the North End. 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.
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.
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". 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. 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. 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.

### 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.

## Historical leadership
### Boss

* 1961–1965 – James "Buddy" McLean – Murdered on October 31, 1965.
* 1965–1978 – Howard "Howie" Winter – Jailed in 1978, released in 2002, died in 2020
* 1978–1995 – James "Whitey" Bulger – One of the most infamous Irish Mob bosses. Fled Boston in 1994 due to a pending federal indictment. He was on the FBI's Ten Most Wanted list until his arrest in Santa Monica, California, on June 22, 2011. He had a $2 million bounty on his head. Killed in his cell at age 89 the night after he was transferred USP Hazleton on October 30, 2018.
* 1995–2000 – Kevin Weeks – Was Bulger's lieutenant, he was arrested on November 17, 1999 and became a cooperating witness in January 2000; released from federal prison on February 4, 2005, he wrote a book in 2006 entitled Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob

## Former members and associates

* Phil Costa – Costa was an underling and gofer of Stephen Flemmi who acted as a bagman and tended bar at afterhours clubs. One at least one occasion during the 1980s, he delivered quicklime to Flemmi and James Bulger as they buried a murder victim in a South Boston home. Costa died in 1999.
* Stephen Flemmi – Whitey Bulger's partner who was arrested in 1994, currently serving a life sentence.
* Vincent "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.
* George Kaufman – 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. He was indicted along with other gang members in January 1995. Mortally ill, Kaufman died in April 1995.
* Johnny Martorano – Notorious contract killer and charter member of the gang, involved in 20 mob related killings, served 12 years in prison for murder.
* Patrick Nee – An associate of Bulger and Weeks and gunrunner; released from prison in 2000 and wrote the book A Criminal and an Irishman in 2006.
* 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. Sims was imprisoned after being captured in Key West, Florida in 1982. He disappeared following his release from Walpole State Prison in 1987.

## List of murders committed by the Winter Hill Gang

| Name | Date | Reason |
| Michael Milano | March 8, 1973 | Bartender Milano was shot by John Martorano after he was mistaken for Alfred "Indian Al" Notarangeli, a rival gang leader. |
| Albert "Bud" Plummer | March 19, 1973 | Plummer, 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. |
| William O'Brien | March 24, 1973 | Notarangeli gang member O'Brien was shot as he drove in South Boston. |
| James Leary | April 3, 1973 | Leary was a member of the Notarangeli gang. He was shot in Miami, Florida. |
| Joseph "Indian Joe" Notorangeli | April 18, 1973 | Notorangeli was the brother of Al Notorangeli. He was shot at a payphone in Boston. |
| James "Spike" O'Toole | December 1, 1973 | Former Charlestown Mob associate O'Toole was shot in the head by Joe McDonald at a bar in Boston after he had wounded Vincent Flemmi in a shooting. |
| Alfred "Indian Al" Notarangeli | February 21, 1974 | The leader of a rival gang, Notarangeli was shot and killed by Martorano after several failed attempts. Notarangeli's body was left in the trunk of his car. |
| James Sousa | October 1974 | Sousa was killed by Whitey Bulger and Stephen Flemmi after he was arrested and charged in connection with a botched robbery of a dentist in which he participated with Bulger. Bulger was concerned that Sousa may implicate him in the crime. Sousa's body was buried in Boxford by McDonald and Jimmy Sims and has never been recovered. |
| Paul "Paulie" McGonagle | November 20, 1974 | 36-year-old McGonagle was a former member of the Mullen Gang and a rival of Bulger in South Boston. He wash shot by Bulger after being lured into a car in the Lower End. McGonagle was buried at Tenean Beach in Dorchester, and his body was found in September 2000. |
| Edward George Connors | June 12, 1975 | Connors 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. |
| Thomas "Tommy" King | November 5, 1975 | Mullen 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. His body was buried near the Neponset River in Quincy. King's remains were unearthed in September 2000. |
| Francis "Buddy" Leonard | November 6, 1975 | Leonard, a friend of King, was killed to divert attention from King's disappearance. He was found shot to death in King's car. Bulger spread the rumor that King had killed Leonard. |
| 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. He was shot and left in the trunk of his car. |
| Roger Wheeler | May 27, 1981 | 55-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. |
| Debra "Debbi" Davis | September 17, 1981 | Davis, 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. She was buried under the Neponset River Bridge in Quincy. Davis' body was recovered in October 2000. |
| Michael Donahue and Edward Brian "Balloonhead" Halloran | May 11, 1982 | Bulger killed Halloran and Donahue in a drive-by shooting using a carbine rifle in South Boston. 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. |
| John B. Callahan | August 2, 1982 | Callahan 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. Callahan's body was found in the trunk of a car at Miami International Airport. |
| Arthur "Bucky" Barrett | November 30, 1983 | 46-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. 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. Bulger then shot him. 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. His remains were retrieved in January 2000. |
| John McIntyre | November 30, 1984 | 32-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. He had implicated the pair in a plot to ship guns to the IRA. 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. His remains were found in January 2000. |
| Deborah Hussey | January 1985 | 26-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. Hussey was first buried in the basement of the house. In October 1985, her body was reburied in Dorchester with two others. Hussey's remains were found in January 2000. |