Howie Winter, former head of Winter Hill Gang, pleads not guilty to extortion charges; released on $25,000 cash bail

By John R. Ellement and Martin Finucane, Globe Staff

SOMERVILLE — Howie Winter, the 83-year-old former head of the notorious Winter Hill Gang, was released on $25,000 cash bail after his arraignment today in Somerville District Court on charges of trying to extort money from two people.

Judge Neil Walker scheduled another court date for July 26 for Winter and his alleged accomplice, James Melvin, 70, of Braintree, who both face charges of attempted extortion and extortion conspiracy.

Prosecutors say Winter and Melvin tried to extort $35,000 apiece from two men, repeatedly threatening them during a series of meetings, phone calls, and voicemails. Assistant Middlesex District Attorney Stephen Gilpatric said Winter and Melvin made repeated references to the North End, invoking the shadowy powers of organized crime.

The victims then went to authorities and cooperated in an investigation, Gilpatric said.

But attorneys for the defendants offered a different scenario, saying their clients were acting to aid a lawyer who was himself being extorted by the two men that the government is now portraying as the victims.

Attorney Peter Mullane, asked if extorting money from people who are extortionists might still be a crime, said, “You know, there’s an old saying: ‘The road to hell is paved with good intentions.”

Martin Weinberg, who is representing Melvin, said that secretly-recorded tapes that are part of the government’s case “may very well prove that there was no criminal intent.”

Gilpatric asked the judge to set bail at $100,000. While acknowledging that both men had no recent entries on their criminal records, he suggested they might flee to avoid spending their latter years in jail.

“They have access to money. Given their age, they have every incentive to flee the jurisdiction,” Gilpatric said.

Weinberg said police had searched his client’s home and found no large hoard of cash. He said his client had no criminal charges since 1999, when he was paroled from federal prison for a bank robbery conviction.

He said his client was married and had three children and six grandchildren. “He had a nice life until last night,” he said.

Winter was the predecessor of gangster James “Whitey” Bulger as head of the Winter Hill organization.

Winter and Melvin repeatedly met with the victims at the Sons of Italy club in Medford beginning in February, ­Middlesex District Attorney ­Gerard T. Leone Jr.’s office said Thursday in a statement.

When one victim asked who Winter was, Winter allegedly said, “There’s no one in the [expletive] country that don’t know who I am,” 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 an 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 in on the two vehicles the men were traveling in at the time and seized two submachine guns and other firearms.