Former Somerville crime boss Howie Winter — “Whitey” Bulger’s predecessor as head of the Winter Hill Gang — has died, his lawyer confirmed to the Herald. He was 91.
A wake at the Doherty Funeral Home in Somerville is set for Monday evening, with a funeral service on Tuesday at nearby St. Clement’s Church, lawyer Peter Mullane said.
“I will miss him, he was a special friend,” said John Martorano, an ex-hit man who teamed up with Winter in the early 1970s.
Winter was also an indispensable source for Anthony Amore, head of security at the Isabella Stewart Gardner Museum, who still to this day is trying to recover $500 million in artwork stolen from the Boston museum in 1990 by two men posing as policemen.
“Howie was a trusted help to me in the search for the stolen paintings and helped open up avenues for me that might not have been available without him,” Amore said Friday evening. “I will miss his assistance.”
Amore added he still believes the rare artworks — including by Vermeer, Rembrandt, Manet and Degas — “will be recovered.” There is a $10 million reward for the 13 works of art. Amore would not go into why he still holds out hope the greatest unsolved art heist could one day be cracked. He’ll have to do it without Howie Winter’s inside knowledge.
Winter, who last lived in Millbury, was one of the original members of the Winter Hill Gang (no relation to his name) and a protégé of its first boss, James “Buddy” McLean.
Winter inherited control of the gang when McLean was murdered by the McLaughlin Brothers of Charlestown during the Irish Gang Wars of the ’60s. In 1975, Winter took Bulger under his wing and made him the No. 2 man in the Irish mob. Unbeknownst to Howie, though, Whitey began ratting to the FBI shortly thereafter.
In 1979, using information provided by Bulger, the feds indicted Winter for money laundering, income tax evasion and horse-race fixing. Winter was sentenced to 10 years in prison, and was released in 1987. In 1993, he was arrested for possession with intent to distribute cocaine. He went to jail again after refusing a deal to inform on Bulger.
After his release in 2002, Winter lived quietly as a property manager until 2012, when the then-83-year-old was arrested on charges of attempted extortion and conspiracy after he and a pal allegedly tried to extort $35,000 apiece from two men. He pleaded not guilty, worked out a plea deal and was given probation.
At his arraignment, Winter’s lawyer described Howie and his co-defendant, James Melvin, 70, as “a couple of benevolent, innocuous grandfathers.”
Bulger was murdered in a West Virginia prison in 2018. His family is suing.
