November 14, 2020 – One-time Boston Irish mob boss Howie Winter died of old age this week at 91, in his own bed, a free man. If you know the math for guys who reach the highest levels of the underworld in their careers, you’ll agree, ole’ Howie boy did quite well for himself.
In the Disco era, Howie Winter was the kingfish of Irish organized crime in Massachusetts. Winter led the Winter Hill Gang out of Somerville and South Boston in the 1970s and his arrest for racketeering and horse-race fixing in 1979 laid the groundwork for the ascent of notoriously-psychopathic Irish crime lord James (Whitey) Bulger.
When Bulger took over, he littered the streets with bodies under the protection of the FBI. More recently, he was played on the big screen by the likes of Johnny Depp and Jack Nicholson. The crusty 89-year old Bulger was beaten to death in a West Virginia federal correctional facility in October 2018.
Winter came up in the Boston underworld as a right-hand man to Somerville gangland boss James (Buddy) McLean more than a half-century ago. McClean was slain in the Irish Mob Wars of the 1960s. The McClean crew eventually evolved into the Winter Hill Gang.
At his height of power, Winter was known to a man about town and appeared to enjoy the limelight. He was hired as a consultant on the 1973 Peter Yates’ classic mob-film The Friends of Eddie Coyle, starring an aging Hollywood bad boy Robert Mitchum in a career-highlight performance.
Whitey Bulger acted as muscle for both McLean and Winter before rising to the top of the heap himself in the 1980s and first half of the 1990s with a considerable amount of help from Uncle Sam. Bulger was a valued confidential informant in the Boston FBI office and gave information on a multitude of Beantown gangsters, including Winter and the horse-racing scheme that many in the Winter Hill crew, including him, were nailed and went to prison for.
Winter quietly returned to the Winter Hill under Bulger’s leadership in 1987 and was soon pinched for selling cocaine and put back behind bars. His last run-in with the law was a 2012 bust for extortion. Reports in the wake of his passing show he was working with authorities in the last years of his life trying to solve the infamous Isabella Stewart Gardner Museum Heist, an Italian-mob sanctioned rip-off of a half-billion dollars in precious artwork from the private museum in downtown Boston in the early morning hours of St. Patrick’s Day 1990.