Sitting Down with Howard Winter

The other side of Howie, a discussion on Bulger, and the true story of the “Winter Hill Gang”

Howard Thomas Winter and Ryan after our interview

According to popular belief, Howard Winter was the second boss of the infamous Winter Hill Gang in the Somerville, Massachusetts area, until Whitey Bulger took over in the early seventies. The Winter Hill Gang is often regarded as the most powerful gang in the United States at the time. Through a streak of luck, I was given an opportunity to sit down and interview Howard Winter and get the full true story of his life, which by his account is not what it was portrayed as in the media.

When I was preparing for my interview with Mr. Winter I was anxious. I had done as much research as I possibly could on him, The Winter Hill Gang, and organized crime. To say I was nervous about the interview would be an understatement, Howie was a very well respected person in the Somerville area and I did not want to waste his time. I even ironed and laid out my clothes the night before the interview so I knew would be one hundred percent prepared.

When I walked into The Mount Vernon Restaurant, the location of our interview, I was nervous but the adrenaline of excitement coursed through my veins. Mr. Winter was already sitting in a booth waiting for me, wearing a United States Marine Corp hat, large rimmed glasses, and a brown jacket, he didn’t appear to be someone who was capable of running the underground of Winter Hill. He will be 90 years old in March. At the start of the interview I handed him my list of questions and after two minutes of silence as he read them, he put down the paper and told me that he couldn’t answer the questions, but he would tell me the full true story. I said that would be perfect and he launched into a captivating two-hour story of corruption, innocence, mistakes, and the life of Howard Thomas Winter and the infamous “Winter Hill Gang”.

The Life of Howard T. Winter

“There was no such thing as a Winter Hill Gang. The Winter Hill Gang was a figment of the press,” said Howie at around minute two of his story. My jaw dropped, and I was hooked, he then went on to tell me all about what really happened. He went on to claim that he was always just a “Legitimate guy” who did nothing wrong. He told me that he knew nothing about the fixing of horse races and that he was a peacemaker of sorts, once making an attempt to help bring calm to the streets of the Winter Hill area.

After returning from the Marines, Howie Winter started off his life as a truck driver he and Buddy Mclean bought an old low mileage rig off of some older folks who barely ran it, and they ran the truck day and night until they got things going and that was his job. But the real story started with a group trip up to Salisbury for a labor day weekend trip full of partying went south. Howie was not on this trip but was soon dragged into the chaos the turmoil caused. Georgie Mclaughlin, a “psychopath”  who was a part of the Mcglaughlin gang, and someone who Howie always respected but tried to avoid, stirred up some trouble. Georgie hit on the girlfriend of famous actor Alex Rocco (then Alex Petricone Jr.), this soon led to an intense argument between Alex and Georgie. Another friend on the trip, Red Llyod,  attempted to de-escalate the scenario by offering them to sit down and cool down with a drink, but it was too late and McLaughlin smashed the drink into Llyod’s face, splitting his lip. A fight quickly ensued among the men, but Howie assured me that when these Somerville boys got in a fight and knocked someone down, they would pick them back up afterward. However this time was different and they wanted another friend, Buddy Mclean (the supposed original leader of the Winter Hill Gang) to kill Mcglahlin. Buddy told his friend that he would never kill anybody, but because he had a reputation of being a pretty tough person, he told them that even though it was against his better judgment, he would give Mclaughlin a beating. A couple days later the men pick up an unknowing Howie in a car and asked him what he thought of the scenario, Howie said whatever Buddy thought was fine with him, but Howie didn’t know that Buddy was going to beat him, and Buddy beat Mcglaughlin badly.

After the beating, The Mclaughlin’s put a hit out on Buddy. The McLaughlin gang had tried to plant a bomb on his car, a traditional way for gangs to commit planned murders in Somerville. Fortunately, Buddy caught them in the act and shot at the men, but things would never be the same afterwards. The very next day someone steps out from behind a truck and shoots Bernie Mclaughlin, one of the brothers of George Mclaughlin, as he exits a liquor store, killing him. A day after the shooting police bring in Buddy Mclean and Alex Petricone for the murder of Bernie McLaughlin, the lawyer got the case thrown out for lack of probable cause. Immediately following this Alex, who was described by Howie as a non-violent and legitimate guy, left Winter Hill forever and went to California to go to acting school and eventually become a very successful Hollywood actor under the name Alex Rocco.

After this ordeal, Buddy met with Howie and told him to not get involved with any of this and Howie said that was perfectly fine with him because he was not and did not want to be involved with anything. But a month later, Howie is dragged back into the fighting. The McLaughlin’s had set a bomb on his car. Fortunately for Howie, he was not driving it when the detonation occurs and the bomb fell partially off and only blew up the front portion of the car. But Howie knew that after that he had to change his entire life, “I knew that if I set up any pattern from that day on, I knew I was going to die, you know? As a matter of fact, from then on, I lived my life like I was gonna die”

The Government and Howie

Howie then went on to tell me about his relationship with the government. He claimed that if you are not cooperative with the government, then you are an enemy of the government. He then said that he was not an enemy of the government, but that he disliked the government because people trying to make a name for themselves as prosecutors have been trying for years to lock him up for doing nothing. He then told me how interrogations were done in a way that puts words into people mouths and forces them to become a “rat”. Howie then talked about how he was always polite to the police and FBI when they would come around. Telling me that he always believed he had a good relationship with law enforcement because he and buddy were always polite and kind. Howie calls himself a victim of the government’s systems, and he said the entire Somerville police also believed that he was a victim, going as far to say that, “they were our allies”.

The Fish Market

“Then we got involved with wimpy Bennet and his crew. Wimpy Bennett was a gangster, an Irish mobster, well known throughout. As a matter of fact, he got arrested for having some of the Bronx Bandits money.” Howie then quickly mentioned how during his career as a truck driver he interacted with some of the Bronx Bandits and him and buddy were instructed by them to check their cars for bugs, and they did this, but Howie admitted that neither of them would’ve even known what an FBI bug looks like. Howie also admitted that he was friendly with these people and he would interact with them and other mafia members at the fish market in New York City while doing trucking work for them. He said that at the time of those interactions he and Buddy had no clue the people they were interacting with were big-time mafia guys, but he said while chuckling that they believed they were just regular longshoremen. On occasions at the fish market, Howie and Buddy unknowingly did the mafia guys at the fish market a favor by changing their delivery times by a few hours when “a guy didn’t show up”, this ended up indirectly earning Howie and Buddy some respect and protection from mafia members in Rhode Island.

After mentioning this Howie said, “And basically that’s the story, and there was no such thing as a Winter Hill Gang, that’s all a figment of the press, and as far as like “Wimpy” Bennett Frank Salemme, Stevie Flemmi, when World War Two was going on the United States became partners with Russia and different countries because they had a common enemy, they didn’t want to be involved with Russia and different countries, but because they had a common enemy they had to become allies, and that’s the description I give you when I talk about the Bennett gang which was Bennet, and Salemme, and Flemmi plus other people that got involved. They were enemies of the McLaughlin gang which at the time was the most powerful gang in the country. And here we were two legitimate guys going up against them. And we knew if we caused a problem we would die.” Buddy and Howie had a common enemy with the bennet gang so they became allies in a way. The McLaughlin’s still wanted Howie and buddy dead so they had to do what they did to protect themselves, which led to them working with the bennet gang. It was then when Howie sadly told me that he decided he would cut all ties with his family to keep them safe. After telling me about this he said “We learned fast how to protect ourselves.”

Whitey Bulger and Howie

I then brought up Whitey Bulger to Howie. As most people know, Whitey topped the FBI’s most wanted list after the death of Bin Laden and Whitey was a psychopath and mobster who terrorized the Boston area, and supposedly led the Winter Hill Gang after Howie. In our interview I asked Howie if he knew Bulger, Howie said he met Bulger after everything with the McLaughlin’s was all over. He claimed that Whitey Bulger came to him asking for help creating peace in a gang war between the Killens, who Bulger was with, and the Mullens gang. Bulger saw that the odds in the war were changing and he knew that he was going to die. Howie didn’t understand why Bulger came to him but he offered his help because he was friends with the Irish kids in the Mullens gang and a member of the Killeen gang by the name of Billy O’Sullivan. Howie spoke to the kids and helped them out, he advised them to stop stealing and he gave them all his contacts where they could make money if they started bookmaking, and that’s how the Mullen gang started their booking. But the peace did not last and the Mullen gang got wiped out one by one.

Whitey went on to say that he pittied Whitey’s brother Billy because Billy, who was a high-powered politician and president of Umass schools, lost everything by sticking up for his criminal brother and keeping quiet about it. Howie knew Billy and his mother and said they were “fine people”. Howard launched into another story of running into Billy at a restaurant while Whitey was on the lamb and they exchanged a friendly embrace in which Howie told Billy he admired him for sticking up for his brother and Billy thanked Howie and walked him to his car. Howie felt as though he had a good relationship with the Bulgers and said that “even today I felt like calling him when they killed him.”

Besides helping Whitey with the gang war, Howie had no other contact with Bulger and believed that Bulger always was good at hiding his true evil personality from the world. Howie said that at the time he didn’t know of Whitey’s crime and he believed that Bulger was just “a legitimately good guy trying to make peace and get on with his life.”

Howie did, however, tell me that he believed the death of Bulger was in part the government’s fault. Howie told me that if you are known to be a rat and you are sent to a hardcore prison full of inmate’s that are in there for life, it’s like a death sentence. He said that an inmate with a life sentence has a deathwish and this is something they shouldn’t do because they don’t care if they murder someone because they want to get put on death row instead of rot away in prison. “To be honest if you have the choice between getting a shot in the arm and killing you, or getting life in prison, give me a shot in the arm every day of the week,” Howie said that sending Whitey, who was in a weakened and sickly state, to a prison with known mafia guys with nothing to loose, was a death sentence and the government knew that.

I then went on to ask Howie what his reaction was to Bulger’s gruesome murder in prison a few months back, “I felt bad for his family, ya know? I mean he deserved that, but he didn’t deserve to get sent up there where they beat him to death. Like if the government put a thing in his arm, in his veins, and did him in, that would’ve been a different story. But they gave him life in prison ya know? Maybe they did him a favor by sending him there.”

Howie told me that he believes that when you analyze things that Whitey “was a product of what the government did.” Whitey was a pretty aggressive guy and there’s no doubting that but after his very first offense, a bank robbery. They sent him to Alcatraz, one of the harshest prisons in the country, “A young fair-haired looking boy, what the hell  do you think could’ve happened to him.” Adding on to this Howie told me that during the war they offered Whitey the chance to be experimented on by a Harvard professor Leary, testing numerous drugs, including LSD, in exchange for a shorter sentence. Whitey volunteered for the study, “God knows what that did to him.” said Howie (Howie also stated that Bulger may have been in Leavenworth, which is one step below Alcatraz when the experimentation was offered to him). Because Bulger was offered to try these dangerous experiments and because he was put in a tough prison like Alcatraz as a first-time offender Howie believes that Bulger became what he was due to these costly mistakes made by the government.

The Horse Race Fixing Charges

Howie himself has spent a good deal of time in and out of prison, so he has a credible grasp of prison life, “I was in almost every can in the country, Atlanta, Memphis, Texarkana, they just keep busting you around.” He also recalls prison life being especially hard for inmates who were imprisoned for organized crime. If you had an “O.C.” stamped on your papers, even if it was your first offense, you were treated terribly and often spent a lot of time “in the hole”, a dungeon-like area with awful conditions, a place where Howie was forced to spend a great deal of time.

This conversation of prison life prompted Howie to briefly tell me about his imprisonment over the fixing of horse races. He claimed that he was never even at the race track and, “if they charged me with bookmaking I would’ve plead guilty to it, but charge me with race fixing, never happened, that was just O’Sullivan the prosecutor trying to make a name for himself, and by the way, he used to sell football cards for us.” He then told me a story that reassured my belief in his good relationship with the Somerville police. There was a shooting at the Capitol Cafe, where Howie and his friends were hanging out, and one captain on the police force told Howie to get in the car with him and told then-young Howie that he had better eyesight than him and handed the gun to Howie and instructed him to shoot the suspect if he saw him and give the gun back after he shot it. Howie didn’t see the suspect but this backed up Howie’s claim of the trusting relationship he had with the police in Somerville. He also said that he and Buddy grew up with many of the members of the Somerville Police Department and that those people would not have helped them if they didn’t know for sure that they were actually innocent people. And he went on to talk about how the police tried to protect them from the mafia and how he and Buddy always tried to help the police out when they could.

I then asked Howie how he felt about Bulger ratting him out to law enforcement about the horse race fixing. Howard took the time to explain the entire situation to me. Whitey and Flemmi were both involved in the horse racing scheme, they were much more involved than Howie ever was because Howie was just a bookmaker taking bets. But Whitey and Flemmi both got their names removed from the inditement because they were FBI informants, but at the time Winter didn’t know of this. Howie admitted to helping move bets and financing the horse but he said he never helped fix the races or ever stepped foot on the track. In fact, when a jockey was brought to trial and questioned he said that he had never even known Howie. Despite this, Howie lost the case and was sent to federal prison, and he blames this on the press’ image they created of the “Winter Hill Gang”. He claims that he never led or wanted to lead anything and that even when he associated with Bulger and Flemmi, he never got involved. Stating that even when Flemmi and Bulger would beat someone in his garage he would sit in the corner and keep quiet, he wouldn’t even sit in his office. He claims he indirectly got the reputation of being a leader of a gang that never really existed. “Bulger and Flemmi and those guys never had nothing what-so-ever to do with a so-called “Winter Hill Gang”. So you got a pretty good story there”

After Thoughts

After generously telling me his life story I got to sit down and chat some more with Howard and have a conversation in which we talked some more about prison life, the mafia, politics, education, and Howie’s personal life. Howie told me how he believes the mafia was a necessary evil and was not entirely bad as they keep drugs away from kids and kept the street thugs in check, keeping the North End safe in the dangerous moonlit hours in Boston. He also cleared up the often disputed owner of the Marshall Street Garage the “gang” was operated out of, some say it was Bulger’s name on the deed, some say it was Winter’s. Winter cleared up the confusion and laughed saying that Cyrus Winter, his dog, was the name put on all the papers for the building. Howie also gave me a glimpse into his personal life today, telling me that he loves helping other people when he can and that he gives all the kids in his neighborhood $5 for each “A” they get on their report cards. He also told me that he never hurt anybody for money and that I should never harm anyone just to get money. He told me that education is the foundation for my future and told me to continue with school and my studies, and giving me very important advice telling me to, “Be an A student and don’t take any shit from your peers. Stay away from any drinking and partying.” I found this to be very good advice and I’m going to do what I can to follow it and take it to heart.

Howie ended our interview by telling me that he thought my family were very good people and said that he did the interview because he had so much respect for my family. Coming from somebody as well respected in Somerville as Howard Winter, that meant a lot to me to hear, I thanked him for being willing to tell me his story and for taking the time to sit with me and talk, I gathered my notes, shook his hand, and headed toward the office and excitedly began planning out this article.


The Winter Hill Gang: A gang whose actual existence is disputed. Operated in the Sommerville/Winter Hill neighborhoods and is beloved to be controlled by James “Whitey” Bulger after the horse race fixing trials.


Howard Winter: Portrayed as a mobster through the media who was the second boss of the Winter Hill Gang. The true story of his life spoken from the man himself is the subject of this article.


Horse Race Fixing: the unethical practice of purposely dropping a high-cost horse into a lower level handicapped race through purposely losing many races. So when the high-level horse is in a low-level race it is a guaranteed win.


James “Whitey” Bulger: psychopath mobster who terrorized the Boston area for years and topped the FBI most wanted list after Bin Laden’s death. Committed numerous murders and was tracked by the FBI for years. He was also an FBI informant which helped him stay on the lamb for years. He was ultimately captured in Santa Monica, California in 2011. He was murdered in prison on October 30, 2018.


FBI Informant: a criminal who gives information to the FBI in exchange for freedom from capture.


Alexander Petricone “Alex Rocco”: A friend of Howard Winter’s who got in trouble with Buddy McLean early on and left to California to become an actor in Hollywood under the name of Alex Rocco. Playing parts in many movies and TV shows including roles in, The Godfather, A Bug’s Life, The Famous Teddy Z, and The Simpson’s.


James ”Buddy” McLean: Good friend of Howard Thomas Winter. Portrayed as the first leader of the “Winter Hill Gang”


Billy Bulger: successful politician and worked a high powered job at UMass. Brother of James “Whitey” Bulger


Georgie McLaughlin: One if the McLaughlin brothers who was a member of the McLaughlin Gang and was known for his “psychopathic” personality.


Stephen Flemmi: James Bulger’s right-hand man, committed many murders and was also an FBI informant.


Winter Hill: A neighborhood in Somerville Massachusetts.


Mullen Gang: An Irish-American Gang that operated in the south Boston area from the 50s-70s. A rival gang of the Killeens.


Bennett Gang: A Boston Gang that shared a common enemy with Howard Winter and Buddy McLean, the McLaughlin Gang


Killeen Gang: A Boston-based crime group that operated in the same area as the Mullen Gang and feuded with them.


McLaughlin Brothers Gang: A gang based out of Charlestown Massachusetts. Run by the McLaughlin Brothers, who used to be friends with Buddy McLean and Howie Winter before the fateful night in Salisbury that put everything in motion.