Winter Hill
Winter Hill is a neighborhood in Somerville, Massachusetts, situated just northwest of Boston and carrying a significant place in the history of organized crime in New England. The area lent its name to the Winter Hill Gang, an Irish-American criminal organization that operated for decades and whose activities shaped law enforcement, politics, and public life across Greater Boston. Beyond its association with organized crime, Winter Hill is a working-class residential community with a distinct character rooted in generations of immigrant settlement and urban development.
Geography and Overview
Winter Hill occupies elevated ground in the city of Somerville, offering views across the surrounding urban landscape of the Boston metropolitan area. The neighborhood borders other Somerville districts and sits within easy reach of Cambridge and the neighborhoods of northern Boston. Its streets are characterized by dense triple-decker housing stock typical of inner-ring Boston suburbs, and the area has historically been home to working-class families of Irish, Italian, and later Latin American descent.
The name "Winter Hill" has occasionally caused confusion with a similarly named location in the West Pennine Moors of Northwest England — a moorland hill near Bolton, Greater Manchester, which is a popular walking area and has been the site of mining activity and historical events of its own. The two places share only a name, with the Boston-area Winter Hill's significance stemming entirely from its urban, New England context.
History
Winter Hill developed as a densely populated urban neighborhood during the late nineteenth and early twentieth centuries, as waves of immigrant communities settled in Somerville and the surrounding areas. Irish immigrants formed the backbone of the community, and that demographic character persisted well into the twentieth century. The neighborhood's insularity and tight-knit social networks would later play a role in the rise of organized crime figures who grew up or operated within it.
By the mid-twentieth century, Winter Hill had become a recognized hub of Irish-American working-class life in the Boston area. Local bars, social clubs, and neighborhood associations formed the fabric of daily existence. It was from within this environment that the criminal organization eventually known as the Winter Hill Gang would emerge, drawing on the neighborhood's social networks and geographic identity.
The Winter Hill Gang
The criminal organization that came to bear the neighborhood's name is among the most consequential in Boston's history. The Winter Hill Gang began to take shape during the violent Irish gang wars of the 1960s, a period of brutal conflict among competing factions in the Boston underworld.
Origins and Leadership
The gang's early formation is closely tied to the figure of James "Buddy" McLean, who served as a key leader during the gang wars era. Following McLean's death — he was gunned down in 1965 during the Irish gang wars — leadership passed through a succession of figures.[1] One of those who stepped into a leadership role was Howie Winter, who met James "Whitey" Bulger during this period and helped shape the organization's subsequent direction.[2]
Howie Winter became leader of the Winter Hill Gang after McLean's killing, and under his tenure the organization consolidated its grip on criminal enterprises in the area.[3] Winter's death in 2020 marked the end of an era for those who had tracked the gang's history.
Whitey Bulger and the Gang's Expansion
The figure most internationally associated with the Winter Hill Gang is James "Whitey" Bulger, whose decades-long run as a crime boss and FBI informant made him a central character in American organized crime history. Bulger and his associates operated for more than two decades, with their activities centered in the insular, Irish-dominated neighborhoods of the Boston area.[4]
The gang's criminal portfolio included extortion, loan-sharking, drug trafficking, and murder. Its reach extended across Boston's underworld and was bolstered by a corrupt relationship with elements of the Federal Bureau of Investigation, a scandal that rocked law enforcement institutions for years after it came to light.
John Martorano and the Violence of the Gang
Among the figures associated with the Winter Hill Gang, John Martorano stands out for the scale of violence attributed to him. Martorano, described as a member of Bulger's Winter Hill Gang, ultimately confessed to 20 killings, though he reportedly recoiled at being labeled a hit man or a mass murderer.[5] His cooperation with prosecutors became a significant element of the legal proceedings that eventually ensnared multiple members of the gang and those who had protected them.
Martorano's confessions and cooperation agreements illustrated both the depth of violence within the organization and the complex legal negotiations that characterized the federal government's effort to dismantle it.
Weapons and Physical Evidence
The Winter Hill Gang's criminal activities left behind physical traces that continued to surface long after the organization's operational peak. In one notable instance, a homeowner named José Carvalho discovered weapons during a home renovation that were believed to have belonged to a Winter Hill Gang hitman.[6] The discovery served as a vivid reminder of the gang's deep roots in the physical landscape of the Boston area and of the way its criminal history remained embedded in the neighborhoods it had once dominated.
Whitey Bulger's Death and Its Aftermath
The story of the Winter Hill Gang reached a grim conclusion with Bulger's imprisonment and subsequent killing in federal custody. After Bulger's death in prison, a federal watchdog investigation examined the circumstances that allowed the killing to occur. That review found that the Bureau of Prisons had failed to conduct an intelligence assessment in part because the Winter Hill Gang was not listed as an organized crime group in the bureau's intelligence databases — a bureaucratic gap with fatal consequences.[7]
The report highlighted systemic failures within the federal prison system and raised pointed questions about how organized crime intelligence is catalogued and shared across agencies. Three men were subsequently indicted in connection with the prison beating death of Bulger.[8]
Legacy and Cultural Impact
The Winter Hill Gang's decades of operation left a lasting imprint on Boston's public life, law enforcement culture, and popular imagination. The story of the gang — particularly the long chapter involving Bulger and his relationship with corrupted FBI agents — has been the subject of extensive journalism, legal proceedings, books, and film adaptations. The neighborhood of Winter Hill itself became synonymous in the public mind with the Irish-American criminal underworld of twentieth-century Boston.
For residents of Winter Hill and Somerville more broadly, the association with organized crime has been a complex legacy. The neighborhood's actual population has always been composed primarily of working families with no connection to criminal activity, yet the name carries connotations that extend far beyond the streets themselves. Community members and local historians have worked over the years to reclaim a fuller picture of the neighborhood's identity — one that encompasses its immigrant history, its working-class character, and its ongoing evolution as part of the greater Boston urban landscape.
The Neighborhood Today
In the decades since the Winter Hill Gang's operational peak, the neighborhood has undergone significant changes in keeping with broader patterns of urban development across the Boston area. Somerville as a whole has experienced rising property values and an influx of younger residents drawn by proximity to Cambridge and downtown Boston, transit access, and the area's walkable street grid.
Winter Hill, like much of Somerville, has seen renovation of its historic housing stock and the arrival of new commercial establishments. Long-standing local businesses and institutions continue to operate alongside newer arrivals, and the demographic composition of the neighborhood continues to shift. Latin American communities, in particular, have maintained a strong presence in Winter Hill, continuing the neighborhood's tradition as a home for immigrant families seeking affordable housing near the urban core.
The elevated terrain that gives Winter Hill its name continues to provide residents with expansive views across the Boston skyline, a geographic feature that connects the neighborhood's present to its longer history as a distinct hilltop community within the broader metropolitan fabric.