Winter Hill is a section of Somerville, Massachusetts. Howie Winter is a person. The Winter Hill Gang was not named after Howie but the section of Somerville where Howie had a garage, Motorama Auto Sales, on Marshall Street. The garage is now a church. Howie’s group hung out there. Frank Salemme said he sent his partner, George Kaufman, to Somerville to help Howie set up the garage operations.

After James “Buddy” McLean was murdered in October 1965, the heir apparent to the McLean gang was Howie. Some suggest that Howie, at the time, served as McLean’s bookkeeper. When Howie’s car was blown up, Howie put the books down and picked up a gun. He would grow into a full-time murderous hoodlum as time passed. Howie was born in the same year as Whitey Bulger and unlike most of the other hoodlums, he died at age 91 on November 12, 2020.

The former head of the federal organized crime strike force, Jeremiah “Jerry” O’Sullivan, was asked at hearing before a Congressional Committee about Howie’s actions. O’Sullivan answered something to the effect: “what gang are you talking about? The Winter gang or the Winter Hill gang.”

I recall his response taking me by surprise. I thought, “wasn’t there only the Winter Hill gang?” It turned out O’Sullivan was right, there were two gangs. The first was the Winter Gang which formed from the remnants of McLean’s gang; later in the early 1970s, it would be incorporated into the Winter Hill Gang when other gangsters such as John Martorano and James “Whitey” Bulger joined it.

I’m going way off subject here, but I feel it is necessary to say something about Jerry O’Sullivan. He has taken a lot of raps after his stroke in 1998 and subsequent untimely death in 2009 at age 66. Although I thought he was totally wrong in the handling of the case and prosecution of Massachusetts State Trooper John Naimovich, I came to recognize that he had been deceived by the FBI and was acting upon what those agents told him. When I heard Naimovich was indicted, I called him. I told him he made a mistake. He said they had information he was a long-time leak to the Mafia. I told him it could not be so.  I had worked with him for years.  I explained I heard he was indicted for giving back some items seized from a bookie.

I spelled out that to him that Naimovich had given Jimmy Katz back some of the stuff we seized at a recent raid, but It was at my direction. We were trying to flip Katz. If we could have flipped him, we would have had a higher up source inside the organization which Katz was member. A decade later we learned that group was the one run by Whitey Bulger and Steve Flemmi.

John Naimovich

O’Sullivan said Naimovich’s indictment had nothing to do with the Katz stuff. It was clear I was not going to change O’Sullivan’s mind especially when Naimovich’s  arrest hit the newspapers. It would also turn out that a decade later the FBI agents participating in the investigation of Naimovich were protecting Bulger and Flemmi.

I would learn later that the witness against Naimovich was one of his informants named McIntyre. The FBI did a wiretap on McIntyre’s bookie operation. This was odd in itself because McIntyre was a low-level bookie. What made it a total aberration was that the FBI agents knew McIntyre was one of Naimovich’s informants.

It know this because a State Police captain who was working closely with the FBI was put in charge of Naimovich’s group in the State Police. One of the first things he did was require that the members of the group disclose the identities of their informants.

Naimovich was intercepted talking to McIntyre over the phone. When the FBI agents arrested McIntyre for booking, they asked McIntyre about his involvement with Naimovich. McIntyre said Naimovich was on the level.

McIntyre was told to go home and think about his answer and come back in a day. It was then explained to McIntyre by O’Sullivan that McIntyre would be put in prison for a long time, the government would seize all his assets, and his wife and kids would be put out on the street unless McIntyre came up with something on Naimovich.  This was the same tactic used on Barboza.

A day or two later McIntyre came back with a story of having paid Naimovich some money for protection. McIntyre’s new story satisfied O’Sullivan. Little did anyone know at the time that O’Sullivan operated in abject fear of the FBI. Years later at a Congressional hearing he explained the FBI could ruin him if he did not do what it wanted.

Some FBI agents wanted Naimovich out of business and pushed O’Sullivan to accomplish their goal. Naimovich was interfering in the gaming business of their top echelon informants. As I mentioned, Naimovich was acquitted after trial. It is a long story that will provide some compelling reading another day.

This might seem somewhat contradictory but what I otherwise knew of O’Sullivan is that he was an honest, capable, and highly skilled prosecutor. He suffered much libeling from people who knew either nothing about him and his excellent ability to prosecute cases or were seeking revenge for his prosecution of the gangsters. Remember this about O’Sullivan, he put the leadership of the Winter Hill Gang in prison. He put the leadership of the Boston Mafia in prison. The friends of those evil people had every incentive to damage his reputation.

James “Whitey” Bulger

James “Whitey” Bulger, during his trial, claimed in a futile attempt to clear himself, that O’Sullivan gave him secret immunity to commit any crime he wanted to do, sort of like a presidential pardon for life. Whitey told a tale that a priest friend set up the meeting with O’Sullivan. They met secretly on a Boston street one night as O’Sullivan was heading for North Station to take the train home.

There was another story FBI Agent John Connolly Whitey’s handler had told. This was before he was betrayed by Whitey Bulger. He said O’Sullivan and Bulger met around Christmas at a hotel because O’Sullivan wanted to meet him.

I had to smile at the audacity of the claim as I listened to it. No prosecutor, never mind a real straight shooter like O’Sullivan, would ever even consider doing such a thing. Deals with a criminal change the parties’ role. It puts the criminal in charge of the prosecutor. His or her independence is forever damaged. That is not to say there is no prosecutor who would ever go over to the dark side. But I am sure O’Sullivan didn’t.

Bulger’s story was that O’Sullivan told him at this unwitnessed meeting that O’Sullivan was afraid of being killed by the Mafia. O’Sullivan wanted Whitey to protect him. As a federal prosecutor, O’Sullivan would surely know that of all criminals, Irish Whitey Bulger was the last person who could protect anyone from the Mafia. Bulger said in exchange for the protection, O’Sullivan offered to give Whitey carte blanche permission to murder, extort, rape, rob or commit any crime he felt like doing.

The story is rubbish. It had not an inkling of truth to it. Whitey’s partner Steve Flemmi who desperately bargained to get out of his jam, never mentioned it. Whitey, when indicted in January 1995 did not mention it when O’Sullivan was still alive. He showed how much he believed in his immunity by fleeing and staying on the lam for 16 years.

Whitey’s defense of total immunity came about because Flemmi previously sought to get immunity for his crime when he alleged that FBI agents gave it to him. The Federal Court of Appeals in Boston reviewed his claim. It noted it was beyond the power of an FBI agent to give immunity. It stated only a federal prosecutor could do that. When Whitey’s turn came to assert his claim of immunity, he knew of the court’s’ decision. He knew he had to assert it came from a prosecutor.

Whitey picked a prosecutor who had died and could not contest his claim. It was the same tactic Steve Flemmi used testifying before Judge Wolf. He identified John Naimovich as the State Trooper who gave him information. John was dead at the time. He could not defend himself. It turned out the cop who gave him information was State Trooper Richard Schneiderhan who was very much alive.

The Winter gang had four lead actors in it: Howie Winters, Joe McDonald, a mean drunk who often went on long benders, Jimmy Sims, and Sal Sperlinga. They were all tough guys. McDonald and Sims were not disinclined to murder people; Winters and Sperlinga were more into loan sharking, strong arming, and gambling. They all were involved in thefts from the waterfront through their longshoreman connections and hijackings.

McDonald would end up dying of natural causes; no one seemed to know what happened to Jimmy Sims. Street talk said he had a falling out with his partner Joe McDonald. McDonald then murdered him and disposed of his body. Some say Stevie Flemmi murdered him. Howie Winter who I mentioned previously was still in the crime business at age 83 when he was arrested for attempted extortion.

Sal Sperlinga had been arrested for extortion involving pinball machines in 1977 along with Winter. They were convicted in February 1978. Winter was sentenced to 18 to 20 years. Sperlinga got 9 to 10 years. Sperlinga, 52, was out on bail waiting for his appeal when on January 4, 1980, before noon, he was playing cards at a club in Magoun Square in Somerville. Daniel Moran walked in and asked “Has anyone seen Sal?” Then Moran saw Sal. He cornered him and shot him several times, killing him.

At the time, the media speculated that with Sal’s death and Winter imprisonment, “Winter’s so-called Somerville gang was in disarray and struggling against outside attempts to gang control.” A newspaper report indicated the gang was virtually leaderless, “a segment of the mob which operates out of Boston’s North End, had indicated it would attempt to take over Winter’s operation.” The report continued that organized crime experts heard rumors that “one former Winter associate, a fugitive since his indictment in the race-fix case” was coming back to take over “administration of the so-called Winter Hill gang for Winter.”

It was all nonsense. The gang, or what was left of it, was in the hands of Whitey Bulger and Steve Flemmi.  By the time of his murder, Sperlinga was no longer a big player.

John Martorano

It was sometime in 1972 or 1973 that the gang went from being the Winter gang to the Winter Hill gang. John Martorano and Whitey Bulger started to hang around in Somerville. They would be joined by Martorano’s brother Jimmy for a time, but he drifted in and out, eventually associating more with guys from the Boston Mafia. In 1974 it received an additional boost when Steve Flemmi, who was on the lam, came back to the area courtesy of the FBI who managed with the help of FBI agents to take care of the cases pending against him. Flemmi joined the group.

There, of course, were other guys who hung around with the group, but they had much lesser roles. John Martorano said when they joined up with the Winter gang, it was decided that each of the partners, Winter, McDonald, Sims, Whitey and he would keep whatever business they had. In their new venture, which was going to be shaking down the independent bookies and making them pay tribute, they would split the money. Four of the partners would get one-sixth each; Whitey would get one-third because he claimed that had to split the money with the Mullen gang in Southie. Martorano doubted that Whitey ever did that.

Martorano said when Flemmi came back to Boston in 1974 he was a different guy. He would sit around and say little. He and Whitey eventually started to do their own thing because they were into staying fit, avoiding drugs and alcohol, not partying, or enjoying the night life. It was said of them all that mattered was money and women.

Stephen Flemmi

Martorano said, “Increasingly Stevie and Whitey kept to themselves, which was just as well. From what they were starting to see and hear, the rest of the gang at the garage didn’t really want to know what Stevie and Whitey were doing in their spare time.” Martorano was the guy who the so-called organized crime guys in law enforcement speculated was going to come back and take over Winter Hill after Sperlinga’s murder. He had gone on the lam when the indictments in the race-fixing case being prosecuted by Jerry O’Sullivan came down in February 1979.

Martorano suggested he continued to be a member of the Winter Hill gang when he was away for 16 years yet complained the other members were not giving him his share of the money. Most of the money Martorano received when in Florida came from his own operations in the Boston area run by Joseph Yerardi, another bookie I prosecuted and convicted. George Kaufman was Martorano’s contact and sent him the money.

Stevie and Whitey

The Winter Hill gang ceased to exist after a short life span. By 1978 – 1979, Bulger and Flemmi took control of the gang.  They moved the operations out of Somerville to a garage on Lancaster Street in Boston’s North End by 1980. The idea that Winter Hill was a gang at that time is tenuous because the only members were its two leaders. It pretty much functioned without help from others. Bulger and Flemmi found they had sufficient muscle between them to continue causing bookies to pay tribute, keep up relations with the Mafia, and extort people.

Why have a big gang where you have to split the proceeds among that many more people?  Why indeed when you have a big backer keeping your operations safe? Bulger and Flemmi were in a unique position. As shown with the Naimovich indictment and in the subsequent court proceedings, the FBI had their backs making sure their operations were not interrupted. Bulger and Flemmi were both in the FBI Top Echelon Informants Program. In a very real sense, they were in partnership with the FBI.

Where the Mafia had a gang type structure with the boss, the underbosses, captains and soldiers, no such thing existed with Whitey and Flemmi. The Mafia had members that it could send to murder, extort or scare other people; Whitey and Stevie only had themselves. Hang-around guys would help Bulger and Flemmi with minor things, but they were mostly slugs who came and went. At one-point Kevin Weeks became a third associate and was usually in the company of Whitey but no one really feared him.

This section deals with the Winter Hill Gang when it was operating under the direction of Howie Winter as he transformed from bookkeeper to life taker. I divided the section into three parts: the murders for the Mafia; the South Boston murders eliminating Whitey’s competition; and the other murders to protect itself or its partners.

6 thoughts on “WINTER HILL GANG MURDERS -Overview

  1. Hi Davidf1989
    Thank you for the link.
    Have you read Rifleman by Howie Carr or Hitman by Howie Carr? Both are EXCELLENT books. Of course there may be some misinformation in the books but they are both incredibly engrossing

    1. Thanks Jerome for your reply and I am currently reading Rifleman at the moment. I found some of it to be rather unbelievable such as the idea of Baby Shacks Manocchio once having a relationship with the feds as Flemmi says in the book Rifleman that Manocchio was an informant. But apart from that, I find Rifleman and Hitman to be interesting.

    2. Thanks for your reply Jerome. Yes I have read Rifleman and while it was interesting. I found some of it to be unbelievable such as Flemmi claiming that Luigi Baby shacks Manocchio was an informant. Hitman is also a good book in my opinion.

  2. Whitey had a much better defense than the O’Sullivan permission defense which was nonsense. He was part of the MK Ultra experiment. While in prison he was given LSD as a guinea pig. No one knows what dose he got. A defense using a Psychiatrist diagnosing that the defendant lacked the capacity to form criminal intent to commit a crime. The government could have been put on trial. They may have a difficult time defending their actions. The O’Sullivan story was too fanciful.

    1. hi Jerome have you thought about checking out the double deal podcast? It’s about organized crime in Massachusetts where they look at the Mafia and the Winter Hill Gang. Here is the link to the podcast according to the people on the podcast the majority of the organized crime figures in Boston were actually informants such as Frank Salemme, Buddy McLean.

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