Charges Outlined Against Former Boss of the Winter Hill Gang

Howie Winter, the former head of the infamous Winter Hill Gang, was arraigned in Friday morning on charges of extortion. He's being held on $25,000 cash bail, and he was also ordered to surrender his passport and wear a GPS tracking device.

At court proceedings Friday, Stephen Gilpatric, assistant district attorney with the Middlesex District Attorney's office, outlined an alleged extortion scheme in which Winter and an associate are accused of meeting with victims in Medford and Randolph, leaving a handwritten note at a victim's home and making expletive-laden threats with references to Winter's connections to organized crime in the North End.

Winter, 83, was arrested at his home in Millbury Thursday night. He and his alleged associate James Melvin, 70, of Braintree, are being charged with extortion and conspiracy.

Melvin was also held on $25,000 cash bail and told to wear a GPS tracking device.

Lawyers for both men said Friday their clients were in fact protecting the two victims from an extortion scheme, not engaging in one. 

Accusations of extortion: threats of North End connections, handwritten note

According to a Massachusetts State Police arrest report, Winter and Melvin tried to convince two victims to cough up $35,000 each.

The story allegedly begins in November of 2011, when a man approached one of the victims and asked for a loan of $100,000 to fund business ventures. The first victim approached the second victim to secure the loan, according to the arrest report.

In January, the man who received the loan allegedly stopped paying it back, and the two victims began receiving phone calls from an unknown man about the money. The man told them to meet at the Sons of Italy in Medford to discuss the third man's outstanding debt, according to the arrest report.

The Sons of Italy is on Broadway, right on Medford's border with Somerville, across the street from Somerville's and not far from the Winter Hill neighborhood.

The arrest report outlines a series of meetings and phone calls in which Winter and Melvin allegedly tried to extort tens of thousands of dollars from the two victims.

During one phone call in March, according to the report and Friday's court proceedings, Melvin, who told the victims his name was Tom, allegedly had a phone call with a victim in which he said, "If you think for one (expletive) minute I'm gonna be (expletive) around with you, you're sadly mistaken. I'm trying to be nice and come meet you so you can tell your side of the story but now (expletive) your side of the story

Melvin allegedly made phone calls to victims from a pay phone, even though he also owned a cell phone, the report says.

During another meeting with the two victims in March, Melvin allegedly said, "So you met Howie (Winter)? So you know what the deal is. Do you know about Howie? … He's been around. He's like this with the North End. They're like that."

Investigators believe references to the North End were to organized crime in that neighborhood.

The report describes another alleged meeting at the Sons of Italy, during which Winter allegedly told the victims they each owe him $35,000.

The meeting was recorded, and Winter allegedly told them, "[L]et me say this to both of you's, OK, you're going to have some problems if you don't come up with some money for these people, bottom line."

Asked why they owed him money, Winter allegedly told the victims, "Because you used someone else's name and they were so (expletive) aggravated that they wanted to come over and bang the (expletive) out of you."

At the meeting, Melvin allegedly told the victims, "He (Winter) came in to straighten it out, now we got the North End involved in this and you know them they want to keep every (expletive) thing quiet."

The victims allegedly experienced other threatening phone calls and meetings with Winter and Melvin.

After a missing a series of phone calls, one victim allegedly came home to find a note that said, "Tom & Friend were here 5-3-12, 1:00, Answer Phone."

Not so, says Winter's lawyer

In Somerville District Court on Friday, Winter's lawyer, Peter Mullane, described Winter and Melvin as "two grandfathers" with "no reason to participate" in such a scheme.

"If anything, they were trying to prevent an extortion that was going on," Mullane said.

After court proceedings, Martin Weinberg, Melvin's attorney, said, "We look forward to defending this case."

Criminal backgrounds

Howie Winter was head of Somerville's Winter Hill Gang in the late 1960s and 1970s. Other than the Italian La Costra Nostra Mafia operated out of the North End of Boston, the Winter Hill Gang was considered the most powerful in the area.

Under Winter's rule, the Winter Hill Gang is said to have made money off gambling machines in bars, forcing bar owners to use their machines. In 1979, Winter and other members of the Winter Hill Gang went to prison for fixing horse races.

With Winter in prison, James "Whitey" Bulger allegedly took over the gang.

For people who grew up in Winter Hill, Bulger was never a true member of the gang, and last year, when Bulger was aprehended after living in hiding for over a decade, .

Winter also served prison time in 2002 on cocain charges, according to the Boston Globe.

Melvin has also served prison time and faced charges for firearms possession and assault and battery in the past. According to Gilpatric, he served time in prison for a bank robbery.

Winter and Melvin's next court date, a probably cause hearing, is scheduled for July 26 at 11 a.m.

More