Howie Winter, the 83-year-old former powerful head of the Winter Hill Gang and the predecessor of gangster James “Whitey” Bulger, was arrested Thursday evening on charges of trying to extort two people, the Middlesex district attorney’s office said.
Authorities said Winter was arrested at his home in Millbury without incident. He is scheduled to be arraigned Friday morning in Somerville District Court, along with an alleged accomplice, James Melvin,70, of Braintree, on charges of attempted extortion and conspiracy.
Former lawyers for the men could not be reached for comment late Thursday night.
Winter and Melvin repeatedly met with the victims at the Sons of Italy club in Medford beginning in February and allegedly demanded that they each pay Winter $35,000, District Attorney Gerard T. Leone Jr.’s office said in a statement.
The victims, whom Leone’s office declined to name, had secured a $100,000 loan late last year for a man who wanted funding for a business venture, the statement said. After the man stopped repaying the loan, Winter allegedly told the victims they had to pay him for loaning out the money without consent, the statement said.
When one victim asked who Winter was and why he was involved in the loan agreement, Winter allegedly said, “There’s no one in the [expletive] country that don’t know who I am,” the statement said.
Melvin, working in concert with Winter, allegedly threatened the victims several times and they feared for their safety, the statement said.
Winter became a mob boss when he replaced Buddy McLean, who was killed in the Irish mob wars in the 1960s. Winter was later indicted, along with 20 other people, on charges that he fixed horse races.
Bulger, who was a FBI informant at the time, escaped charges in the investigation and replaced Winter as mob leader.
Winter was released from prison in the late 1980s, but was later convicted of dealing cocaine. He was released from prison again in 2002 and has been working as a property manager out of his home in Millbury.
Melvin also has a checkered past. He was one of six men convicted in the 1991 attempted robbery of an armored truck in Abington. The FBI moved on the two vehicles the men were traveling in at the time and seized two submachine guns and other firerarms.
In 1998, Winter told the Globe he was surprised to hear that Bulger and Stephen “The Rifleman” Flemmi were federal informants and that Bulger had cooperated with authorities against him on charges that put him in jail.
“It’s still hard for me to believe,” he said.
Federal prosecutors then asked Winter to cooperate against Bulger, who had been a fugitive by then. Winter had four years left on a 10-year sentence. But he refused.
“If it was my worst enemy, I wouldn’t cooperate against them,” Winter said. “Myself, I think I’d rather take a cyanide pill than go to trap someone else to save my own ass.”
Winter also said that he met Bulger in the 1970s, when Bulger enlisted his help in resolving a bloody dispute between rival gangs in South Boston. Bulger later began hanging around Winter Hill in Somerville, eventually teaming up with Flemmi.
During court testimony in 2002, John Martorano, a former hitman for Bulger, implicated Winter in the 1976 slaying of a Revere bookmaker. Winter was never charged with murder.
Court records show Winter has battled health problems in recent years. In a 2006 motion to have his federal probation term shortened, a lawyer for the aging gangster wrote that Winter suffered from prostate cancer and had also been treated for skin cancer on his face and nose. In a filing objecting to Winter’s request, prosecutors called him “one of the most infamous criminals to be prosecuted in this District.”
“The fact that he has complied with these [release] conditions (or at least not been caught violating them) is not a reason to reward him,” prosecutors said.
A judge denied Winter’s request.