Public DomainA 1975 Drug Enforcement Administration chart mapping the hierarchy and inner workings of Bostons notorious Winter Hill Gang.In the early 1960s, a group of Irish mobsters rose to prominence in the Boston area. They were known as the Winter Hill Gang and they were ruthless.Headed by Howie Winter and Buddy McLean, the group slowly eliminated all of its rivals through a series of Irish gang wars until it dominated Bostons criminal underworld. From drug trafficking and fixing horse races to extortion and murder, the organization had a hand in a wide variety of illicit activities. It also allied with the Mafia and this would lead to its downfall.In the mid-1970s, gang member Whitey Bulger began working as an FBI informant, passing on intelligence about the mobs Mafia allies in exchange for the agencys protection. In 1979, the FBI arrested 21 mobsters, leaving leadership of the Winter Hill Gang up for grabs. Bulger swooped in to take control, but he made plenty of enemies in the process.Bulger had to spend much of the rest of his life on the run both from those hed wronged and from the authorities. In the meantime, the Winter Hill Gang slowly fell apart, and it had all but vanished by the 1990s. This is the story of the rise and fall of Bostons most vicious mob.The Winter Hill Gangs Origins In SomervilleThe Winter Hill Gang first emerged in the Winter Hill neighborhood of Somerville, Massachusetts, around 1961. At first, the organization barely resembled the criminal empire it would soon become. Most members were small-time Irish-American criminals who conducted illegal rackets while holding ordinary jobs.James Buddy McLean and Howie Winter quickly became the groups dominant figures. Publicly, they operated trucking businesses. Behind the scenes, however, they expanded gambling operations, loansharking schemes, and bookmaking rackets throughout Boston.Somerville Public Library/FlickrWinter Hill Gang founder James Buddy McLean in a September 1958 mugshot.For a while, McLean and Winter mostly avoided conflict with Bostons other Irish gangs, but that changed in September 1961. Then, Georgie McLaughlin of the rival Charlestown Gang reportedly made a move on the girlfriend of Winter Hill Gang member Bobo Petricone who went on to become an Emmy Award-winning actor under the name Alex Rocco. Petricone and his cronies beat McLaughlin senseless and dumped him outside of a hospital. Georgies brother, Bernie McLaughlin, demanded that Buddy McLean hand over the men who were responsible. When McLean refused, the McLaughlins tried to wire a bomb to his wifes car. So, McLean shot and killed Bernie McLaughlin on Halloween 1961.Bostons first Irish Gang War had begun.Bostons Vicious Irish Gang WarsFor the next four years, gunfire erupted across the Boston area. Rival factions hunted each other down in bars, parking lots, restaurants, and public streets. At least 60 gang members died, and these murders were so commonplace that locals jokingly referred to the obituary sections of Bostons newspapers as the Irish sports pages.LIFEA list of victims of Bostons first Irish Gang War printed in a 1967 issue of LIFE magazine.Hitman Joseph the Animal Barboza later described this blood-soaked era to FBI investigators. As recorded in a 2004 report by U.S. Congress Committee on Government Reform, Barboza stated, They were killing people at bus stops, walking in their houses and killing them, walking in nightclubs and killing them. People were found in suitcases, dissected. Guys were found floating in the river.Georgie recovered from his injuries and was arrested for an unrelated crime, leaving just one McLaughlin brother to take down: Punchy. The Winter Hill Gang first tracked him down as he left a hotel, shooting off half of his jaw. When that didnt kill him, they tried again, blowing off his hand. But still, he survived.They finally succeeded on Oct. 20, 1965, fatally shooting Punchy at a bus stop. By then, most of the Charlestown Gang had been eliminated, but a few men remained and they still wanted revenge.Public DomainJoseph the Animal Barboza was a vicious hitman for the Patriarca crime family who allied himself with the Winter Hill Gang.On Halloween 1965, exactly four years after Buddy McLean killed Bernie McLaughlin, McLean himself was shot dead by Charlestown Gang member Steve Hughes. Hughes own murder the following year marked the official end of the first Irish Gang War. And the Winter Hill Gang had emerged on top.The Winter Hill Gangs Expansion And Power StrugglesAfter McLeans death, Howie Winter took control of the organization. Under his leadership, the Winter Hill Gang absorbed two more rival groups, the Mullens and the Killeens of South Boston. He also teamed up with the Mafias Patriarca crime family.In 1973, the Patriarcas were in the midst of a conflict with a Somerville gang headed by Alfred Indian Al Notarangeli. Winter and his men began taking out Notarangelis cronies in what became known as the Indian War. Notarangeli fled, but he eventually returned to Boston in an attempt to make peace. The Winter Hill Gang accepted Notarangelis offer of $50,000 and then shot him dead two months later.Throughout these wars, the Winter Hill Gang developed a reputation for its ruthlessness. Public DomainWinter Hill Gang members Stephen Flemmi (left) and George Kaufman (right) with Patriarca hitman Cadillac Frank Salemme (center) under FBI surveillance in 1989.The Winter Hill Gang developed a reputation for its ruthlessness. Among its most feared members was John The Executioner Martorano, a hitman who confessed to at least 20 mob-related murders.But murder was only part of the business. During the 1970s, the gang also became heavily involved in fixing horse races throughout the Northeast. The operation worked through a carefully organized system.First, mobsters bribed the jockeys. Then, they drugged the horses, and gang associates placed large bets on races whose outcomes had already been manipulated. For years, this scheme generated enormous profits. But eventually, the operation became too large to keep hidden.Anthony Fat Tony Ciulla, one of the key participants, was arrested and later became a government informant. He exposed the entire conspiracy to federal investigators. Ciulla also named Whitey Bulger as a co-conspirator but the FBI already knew Bulger well.The Rise And Fall Of Whitey BulgerWhitey Bulger had been a Killeen gang member who was absorbed into the Winter Hill Gang in the early 1970s. Shortly after, he began working as an FBI informant, passing the agency information on the Patriarca crime family.Public DomainBefore joining the Winter Hill Gang, Whitey Bulger spent time at Alcatraz for armed robbery and truck hijacking.When the horse race-fixing scheme came to light in 1979, 21 men were arrested, including Howie Winter. But Bulger avoided prosecution due to his role as an informant. When the Winter Hill Gangs leadership went to prison, Bulger took the opportunity to seize power.Alongside Stephen Flemmi who also worked as an informant Bulger continued to eliminate his competition, often using his ties to the FBI to have his rivals imprisoned. In this way, the Winter Hill Gang became even more powerful.Bulgers FBI handler, John Connolly, helped protect the organization. He warned Bulger about investigations, surveillance operations, and potential informants. This led to several brutal murders.In 1979, Bulger and Flemmi began skimming money from World Jai-Alai with the help of the companys president, Jack Callahan. When the owner, Roger Wheeler, became suspicious, he fired Callahan so Bulger had Wheeler killed. Public DomainAn FBI surveillance photo of Stephen Flemmi (left) and Whitey Bulger (right) from the 1980s.John Connolly then told Bulger that the FBI wanted to question Callahan about the crime, so Bulger ordered Callahans murder, too. Connolly was later imprisoned for second-degree murder in connection with the case.During the 1980s, the Winter Hill Gang allegedly helped smuggle weapons to the Provisional Irish Republican Army (IRA) during The Troubles. They partnered with a fisherman named John McIntyre, but McIntyre went to the authorities instead of delivering the guns. Bulger had him killed, too. Eventually, Bulgers crimes grew so obscene that even the FBI couldnt protect him. Connolly retired in 1990, and Bulger was released as an informant. By 1994, multiple government agencies were investigating his crimes, and he decided to go on the run.Bulger wasnt arrested until 2011, and by that time, the Winter Hill Gang had fallen apart. However, its legacy hangs over Boston to this day. From bloody gang wars to one of historys most controversial FBI scandals, the criminal organization left a permanent mark on the city.After reading about the Winter Hill Gang, go inside Whitey Bulgers death in prison. Then, learn the stories of 11 infamous Alcatraz inmates.The post The Winter Hill Gang, Bostons Irish Mob That Rose To Power By Eliminating All Of Their Competition appeared first on All That's Interesting.