Howie Winter, the 83-year-old former head of a Boston-area gang that was later run by James "Whitey" Bulger, pleaded not guilty Friday to attempted extortion and conspiracy charges.
Winter and co-defendant James Melvin, 70, were arrested Thursday after authorities said they tried over several months to extort $35,000 from each of two men who had arranged a $100,000 loan for a third man.
Winter, who headed the Winter Hill Gang in the 1960s and `70s, wore large black sunglasses during his arraignment in Somerville District Court. He and Melvin stood silently as a prosecutor described a series of meetings and phone calls in which the two men allegedly threatened the men and repeatedly referred to the North End neighborhood of Boston in an apparent attempt to intimidate the men through a thinly veiled reference to organized crime.
Assistant District Attorney Stephen Gilpatric said some of the meetings were secretly recorded. In the recordings, Winter and Melvin can be heard threatening the men if they don't pay the money, Gilpatric said.
"You're gonna have some problems if you don't come up with money," Winter allegedly said during one of the meetings.
Winter also expressed disbelief when one of the men told him he didn't know who he was during a meeting in March at the Sons of Italy in Medford.
"There's no one in the (expletive) country that don't know who I am," he responded, Gilpatric said.
Lawyers for Winter and Melvin disputed the prosecutor's account, saying they actually were trying to help a lawyer who was being extorted by the two men prosecutors say were the victims. Neither would identify the lawyer who Winter and Melvin claimed to be helping.
Prosecutors said that a man who needed money to fund a business venture contacted one of the victims to ask about getting a loan. The victim agreed and contacted the second victim, who agreed to loan the man $100,000.
In January, the man allegedly stopped making payments on the loan to the victims. Beginning in February, the victims began receiving phone calls from an unknown man who asked to meet to talk about the money owed to them by the third man.
During an initial meeting, one of the victims met with Winter and Melvin to discuss the third party's outstanding debt. During that meeting, Winter told the victim that he and the other victim were expected to pay $35,000 each to Winter for loaning the third party the money without consent or permission, prosecutors said.
Gilpatric said the two victims contacted law enforcement authorities because they believed that their lives and the lives of their families were in danger.
Over the next few weeks, state police gave cash to the two alleged victims to give to Winter and Melvin to make installment payments on the $35,000 they each were ordered to pay. Winter and Melvin then demanded that each victim pay them $5,000 per month, Gilpatric said.
Judge Neil Walker ordered Winter and Melvin held on $25,000 cash bail, an amount their lawyers said they will likely be able to raise. Gilpatric had asked for $100,000 cash bail, citing both men's long criminal records. If they do post bail, both men will be confined to their homes wearing electronic monitoring bracelets.
Winter led the notorious Irish gang in the 1960s and `70s. Gilpatric described him as a "well-known member of organized crime" and said he had been convicted in the 1970s for conspiracy and racketeering. In 1993, he was sentenced to 10 years in federal court on a conspiracy charge. Gilpatric said Melvin had served a significant amount of time in state and federal prisons for firearms violations and assault and battery. In 1991, he was convicted of conspiracy in a bank robbery and sentenced to five years.
Bulger replaced Winter as leader of the gang after Winter was indicted in a horse race-fixing scheme. Bulger, now 82, is currently awaiting trial for allegedly participating in 19 murders.
Melvin and Winter are due back in court on July 26 for a probable cause hearing.