Once a battleground for Boston’s underworld, Somerville, Massachusetts, has undergone a dramatic transformation—from the reign of the notorious Winter Hill Gang to the rise of gentrification reshaping its neighborhoods. On the latest episode of the Jason Trimmins Podcast, Trimmins takes listeners on a deep dive into Somerville’s history, from its criminal past to its cultural shift.
Somerville’s streets were once dominated by the infamous Winter Hill Gang, led by Buddy McLean, a key figure in the Great Boston Gang War of the 1960s. The conflict erupted after a violent altercation on Labor Day 1961, setting off a deadly rivalry between the Winter Hill Gang and the Charlestown-based McLaughlin brothers.
- McLean’s refusal to hand over a gang member led to assassination attempts, including a car bomb that nearly killed his family.
- In retaliation, McLean shot Bernie McLaughlin in broad daylight, triggering the Irish Gang War that reshaped Boston’s criminal hierarchy.
- After McLean’s death in 1965, Howie Winter took over and expanded the gang’s operations, moving into bookmaking and loan sharking.
While the Irish gangs fought among themselves, the Italian Mafia capitalized on the chaos. Jerry Angiulo, a high-ranking figure in the New England Mafia, reportedly boasted, “I had to bury 20 Irishmen to take over this town.”
By the late 1970s, the Winter Hill Gang fell under the control of Whitey Bulger and Steve Flemmi, two ruthless crime bosses who shifted operations to Boston’s Lancaster Street near North Station. Their rule was marked by a violent grip on Boston’s criminal landscape, aided by corrupt ties with the FBI.
As the Winter Hill Gang faded, Somerville’s streets saw the rise of Latino and Haitian communities, bringing new social dynamics—and new gangs. By the early 2000s, national gangs like MS-13, Bloods, and Crips had gained a foothold.
- The city, once dismissed as “Slumville,” experienced a wave of street violence.
- What started as minor scuffles escalated into deadly turf wars.
- Union Square and surrounding areas became hotspots for gang activity.
By the 2010s, Somerville’s rough reputation began to shift as gentrification swept through the city.
- Housing projects were bulldozed to make way for sleek townhouses and upscale apartments.
- Property values skyrocketed, forcing many longtime residents out.
- The city, once a predominantly blue-collar enclave, became a diverse cultural hub.
- Despite the rapid changes, locals seem less resistant to gentrification compared to other Boston neighborhoods.
While Somerville’s crime-ridden past may seem like a distant memory, remnants of its gritty history remain. On his tour, Trimmins roams the same streets once controlled by the Winter Hill Gang, stops at historic landmarks like Prospect Hill and Dunkin’, and grabs lunch at Mama Gina’s in Union Square—a neighborhood now defined by cafes, condos, and cultural shifts.
Despite its evolution, longtime residents remember when Somerville was a tight-knit community where everyone knew each other—a stark contrast to today’s more fragmented urban landscape.
As gentrification continues, the city balances its notorious past with a new future. But one question remains: Can Somerville hold onto its identity while embracing change?
