Winter Hill Mob- South Boston

Winter Hill Mob- South Boston

Joined: April 15th, 2005, 9:58 am

May 5th, 2005, 12:22 pm #1

Kevin Weeks



Among members of the Boston underworld, no one was closer to "Whitey" Bulger than Kevin Weeks, a South Boston native and loyal tough guy who Bulger groomed as his successor and treated like a son.

During the 1980s, Weeks operated several of the Southie convenience stores and liquor marts that served as fronts for the Bulger organization. Weeks received "rent" payments from loan sharks and bookmakers, insulating Bulger from the transactions, and also helped shake down local crooks and businessmen behind on their debts to the gang.

Following Bulger's disappearance in 1995, Weeks acted as "operational chief" of the Bulger organization, taking orders from the fugitive gangster over the phone and keeping Bulger well-funded by funnelling thousands of dollars into his bank account.

Once Bulger and Flemmi were outed as FBI snitches, Weeks became the target of local mobsters who had been ratted out by the pair. He also grew increasingly bitter toward his former bosses. In 1999, he was arrested and charged in a federal racketeering indictment. Facing the prospect of charges that could send him to prison for life, and with no financial or legal assistance forthcoming from Bulger's ruined organization, Weeks agreed to cooperate against his old boss. In 2000 he led police to the bodies of eight alleged Bulger victims buried in various locations around Boston.
Last edited by IrishHood on December 1st, 2006, 2:35 pm, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

May 5th, 2005, 12:34 pm #2

Stephen 'The Rifleman' Flemmi



A Roxbury native and an Italian-American, Stephen J. Flemmi got his nickname during the Korean War, when he was an uncanny marksman in the Army. In the 1960s, Flemmi developed close ties to both the Irish and Italian mobs, befriending Mafia boss Francis "Cadillac Frank" Salemme and earning a reputation as a cold-blooded operative. He later joined up with Somerville's Winter Hill gang, where he forged a close partnership with "Whitey" Bulger. Flemmi served as Bulger's front man, collecting money from bookies and inspiring fear in those who didn't pay their debts on time. He began informing for the FBI several years before his boss.

Flemmi was arrested in 1995 on charges of racketeering and extortion, but fought the charges on grounds that the FBI had granted him and Bulger permission to commit certain crimes short of murder while they worked as informants. The ensuing court hearings dredged up some of the Boston FBI’s darkest secrets, including revelations of agents accepting payoffs and leaking information to help protect Flemmi and Bulger from prosecution. A judge ultimately ruled that the gangsters had received no promise of immunity, and Flemmi was sentenced in August 2001 to 10 years in prison for extortion and money laundering as part of a plea agreement with prosecutors. However, the deal did not resolve the most serious charges against Flemmi; he still faces 10 federal murder charges and state murder charges in Oklahoma and Florida.
Last edited by IrishHood on November 16th, 2006, 11:31 am, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

May 10th, 2005, 8:35 am #3



Breaking Legs for Whitey
by Edward J. MacKenzie Jr.

In an excerpt from his controversial book, a South Boston drug dealer recalls the dirty work he says he did for the FBI's second-most-wanted man.

On a late January afternoon in 1980, Whitey Bulger stepped from the shadows. I was working out in my second-floor apartment on Boston Street in South Boston, preparing for the Eastern United States Kickboxing Championships. I'd been into serious kickboxing for more than a year and was in prime shape. As always when I was working out, the door to my apartment was open so my buddies could walk in.

I was studying my form in a full-length mirror when I saw a reflection of four guys in the doorway. They gave me a look like they owned the place. "What the fuck are you doing here?" I yelled. Two of them walked right in. The other two stayed at the door. I started toward them, ready to separate their heads from their bodies. "Anyone ever teach you to knock, assholes?"

One of those assholes had icy, blue-gray eyes and receding, close-cropped silver hair, brushed straight back. He was maybe 40 or 50. With his barracuda jacket, jeans, and leather sneakers, he had the Boston docks gangster look. This guy's whole being was ice cold. I was 22 and one tough shit myself, but something made me hesitate. I knew the guy in front of me was someone you didn't mess with.

"My name is Jimmy Bulger," he said. The name didn't register with me. "Most people call me Whitey."

Whitey Bulger. Now that was a name I knew. Bulger pointed to the other man. "This is my friend Stevie Flemmi." Stevie "the Rifleman" Flemmi. I knew that name, also. Whitey didn't introduce the other two.

Standing in my apartment was a stone-cold killer, the most feared and notorious gangster in Boston. Next to him was Stevie Flemmi, born and bred in Roxbury, not Southie, but still the most feared man in Boston's underworld after Bulger.

Whitey was an institution unto himself. Brilliant. Ruthless. Murderous. Lucifer personified. If the word on the street was to be believed — and what other word could I rely on? — Whitey Bulger could kill you and your dog, fuck your wife, burn down your house, and walk away clean. I realized this probably wasn't a visit to say hello.

When Whitey spoke again, his voice was so soft I had to lean closer just to hear him. I learned later that he kept his voice low to avoid being recorded by surveillance devices. The trouble, he explained, was $10,000 worth of Hummel figurines me and a buddy had stolen from some guy's house. What we hadn't known was that this guy was in the mob. Whitey wanted the Hummels returned. Unfortunately, they were long gone. We'd sold them.

"Whitey, we —"

"I prefer to be called Jimmy," he said.

"Jimmy," I continued, "we did take the Hummels. I don't know how much they were worth. I don't know where they are, and I don't think we can get them back. But I'll do whatever is necessary to make things right. I'm working at the Boston Rose Sub Shop. I can make payments every week or whatever to clear this thing up."

Whitey thought for a second, then asked, "Who did you do the score with?"

I gave him the only answer I could, even though I knew I might be signing my death certificate. "Jimmy, I can't say who I did it with. I'm in this on my own."

His eyes hardened. "What the fuck do you mean you can't tell me?" he said, his voice edged, though still barely audible. "This guy is going to kill you. You don't know the rules. No one shits in my backyard without getting my permission."

"Jimmy, I can't give this guy up." I was thinking that if this guy is going to kill me, then if I give up my buddy's name, he's going to get whacked, too. It sounded like an insane reason to die, but it was my code. I honored very little in the world, but the code of not ratting on my buddy was on the top of my list.

That appeared to strike a chord with Bulger. "Okay, I respect that. I respect you won't give up your buddy." Then he leaned back and thought, looking at me all the while. After a few seconds, he said, "I'm going to cut you a favor. You're all set. No one is going to come after you." A wave of relief swept over me.

Whitey extended his hand, which I gratefully shook. "Down the road," he said, "I may need a favor, all right?"

"Jimmy, that won't be a problem." Whitey looked at me for a couple of seconds, always that icy stare, before he turned toward the door. Flemmi and the two other guys stepped aside to let Whitey take the lead. They didn't take their eyes off me until their boss had passed them.

The South Boston I knew so well from the mid '70s through 1990 dripped with Irish pride, love for neighbor, resistance to outsiders, and a desire to run its own show. It was the perfect place for a guy like Whitey Bulger to build a massive criminal enterprise and earn a reputation as a gentleman bandit and legendary street warrior. It was also the perfect place for a politician like Whitey's brother Billy Bulger to build power. I believe that Billy Bulger was, and remains, one of Southie's best assets. I also believe he orchestrated corruption and helped run interference for his brother against law enforcement. Billy had to have known what his brother Whitey was up to.

For a young kid who couldn't imagine winning in life the legitimate way, Southie was its own world with its own rules. Why ever leave? There was always a hustle or deal to make, cheap rent, and a bar on every corner where you had friends to share the booze, the fun, the stories. And if you wanted to go legit, there was always a city councilor who could put you in touch with the right government job. A phone call and a promise of a campaign contribution and, a few Mondays later, you were at the parks and recreation department, housing department, or some other bureaucratic hole in the wall where you could feed at the public trough for as long as you wanted. All most of us needed was Southie, and nothing else.

After I started working for Whitey in 1985, no more than a few days would elapse between jobs; I'd be asked to take care of a situation, to collect some money, or to send someone a message. Most of the time, Kevin Weeks, one of Whitey's top dogs, would call to give me my assignment. When Whitey dealt with me directly, he didn't say much. Sometimes, he wouldn't talk at all. He'd just sit in his car and show me a piece of paper with a name and instructions on it.

Working for Whitey gave me a feeling of ultimate power. With my background as a fighter, selling drugs for Whitey made it inevitable that I would do other things for him as well. Whitey ruled through intimidation and fear. Anyone who assisted him in creating a climate of intimidation and fear became, as the Boston Globe once said of me, a "Bulger favorite."

My job description was simple: From 1985 to 1990, I worked for Whitey as a street soldier, an enforcer, a leg-breaker, a drug-runner. I was the hired muscle who distributed drugs for my boss and broke the limbs of those who disrespected him. I was often sent on missions that made me feel I was pushing up against the icy shoulder of death.

Whitey was 30 years older than me. I wanted to believe that he could give me back some of what I had lost. My parents neglected the family, and all five of us kids were committed to the Department of Public Welfare on May 13, 1963, when I was four. My innocence died early. I'm not trying to place all the blame for what I became on the shoulders of the biological parents who never gave a shit about me. Thousands who grew up like me did not embrace lives of crime. They don't have blood on their hands. I am who I am. For better or worse, this is the man I became.

Whitey was evil incarnate, but he liked me enough to educate me in the ways of the South Boston streets that, despite my smarts, I hadn't yet learned. And I was a grateful student.

Drug dealing got messy sometimes. This one kid owed me about 3,000 bucks at one point. He was new to the drug trade when he started buying from me. It didn't take long before he was screwed up on drugs, and he ran into a cash problem. He didn't have the money to pay me and was so terrified that he bolted. If I really wanted to find him, I could've, but he was a friend of my brother Ronnie, so I didn't expend too much effort tracking him down.

A few years after that, I was at Canobie Lake Park in New Hampshire, and I saw the dealer with his family. Quite a hiding place, huh? When he saw me, he started backing away with this look of terror on his face. I'm convinced he would have left his wife and kids right there. But I waved to him and shouted, "Don't worry. I don't have any problem."

Did he take advantage of the break I gave him? Nah, he came back to Southie and, to make matters worse, was suspected of ratting on the Southie boys. The penalty for treason was death.

One night me and two buddies kidnapped him from his apartment. We duct-taped his arms and legs, threw him into the trunk of a black Ford LTD, and headed out to the Blue Hills in Milton, where we'd put two bullets in the back of his head and bury him. It was the first time I'd had to kill anybody, but I wasn't thinking much about what that meant. It's business. Nothing personal.

We only had a couple turns to make before we were on 93 South, when we saw the blue lights of a cop car flashing. Turned out, our car had a broken taillight. The two cops looked in the car and recognized its occupants. One asked us if we minded if he looked in the trunk. We said, "Yeah, we kind of do."

The trunk was popped, and the condemned man was discovered. Me and my cohorts were arrested on kidnapping charges. They dragged us all into court, but this dealer wouldn't testify against us. The cops had no choice but to release us. I never saw that drug dealer again.

It all fell apart on a hot August morning. I was outside my apartment on Gold Street in South Boston, heading to Connolly's Corner Café, a bar of which I was the manager of record, when I noticed an undercover car slowly driving by with two cops inside.

I said, "Hey there, are you guys looking for me?"

"Who are you?" a cop yelled back.

"Eddie MacKenzie," I said. "And if you want me, here I am."

A few days later, I was standing outside, stretching my legs in the prison yard at the Danbury Federal Correctional Institution in Connecticut with four Southie buddies who were in the can with me. Things happen quickly sometimes. We'd been outside 10 minutes when I saw one of Danbury's most notorious guests, a "celebrity" inmate by the name of Raymond J. "Junior" Patriarca, the Providence-based godfather of the New England Mafia.

Patriarca made a motion with his head for us to walk over to him. We did as instructed. He was on the shortish side, five-six, with olive skin, a Roman nose, and a fat belly. There were no hellos, no pleasantries. Smiling, Patriarca asked, "You know why you're here, don't you?" Without waiting for our response, he dropped the bomb. "You're here because you got ratted out by your boy Whitey. We've known for years he was a canary."

No one spoke. We didn't know what to say to Patriarca, a quintessential Mafia don, no rocket scientist but still a lot wiser to the ways of the street than us.

I didn't believe him right away. We'd all suspected that Whitey had been paying off the feds for years, but this? Suddenly, I felt a deep pain inside that was nothing like fear. Fear I'd learned to deal with years ago. Yeah, I was in jail and I might be going down for 10 years. But that didn't shake me up like this was beginning to do.

Had I been shanked by my boss?
Last edited by IrishHood on September 11th, 2007, 5:30 pm, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

November 28th, 2005, 12:49 am #4

The Winter Hill Gang is a loose confederation of Boston, Massachusetts area, mostly Irish-American organized crime figures. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have included notorious Boston gangster James J. "Whitey" Bulger and hitman Stephen J. "The Rifleman" Flemmi.

While Winter Hill Gang members are alleged to have been involved with most typical organized crime related activities, they are perhaps most known for fixing horse races in the northeastern United States. Twenty-one members and associates, including Bulger's predecessor Howie Winter, were indicted by federal prosecutors in 1979.

The Winter Hill Gang also played a central role in the Boston Irish Mob Wars of the 1960s between Winter Hill leader James McLean and Bernard McLaughlin's Charlestown Mob.

A movie about the Irish Mob Wars, "The Winter Hill Gang," is scheduled to begin production in Boston in fall 2005. The film is rumored to be starring George Clooney, Matt Damon, Ben Affleck, and Mark Wahlberg.
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Joined: April 15th, 2005, 9:58 am

November 28th, 2005, 12:53 am #5

James "Buddy" McLean was the first leader of the Somerville, Massachusetts Irish gang known as the "Winter Hill Gang" in the 1960s. After Charlestown, Massachusetts mobster Bernie McLaughlin's assassination attempt, McLean shot him dead in Charlestown, in broad daylight. Although he was acquitted of all charges, Mclean was later shot dead by "The McLaughlin Brothers" gang assassin Cornelius Hughes. He was succeded by Howie Winter and later James "Whitey" Bulger.

Last edited by IrishHood on November 30th, 2006, 12:22 pm, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

January 24th, 2006, 11:44 am #6


James P. Flynn (born February 5, 1934 in Boston, Massachusetts). An Irish-American Bostonian, teamster, and film actor. He was a reputed member of the famous Winter Hill Gang.

Jimmy Flynn has appeared in many films shot in the New England area. He has also been the Teamster Union's coordinator on film shoots. One of his best friends is Stephen "The Rifleman" Flemmi, a professional hitman spending time in prison.

In 2000 Flynn ordered a snack truck owner and operator Susan Christy who was working on the film set of "What's the Worst That Could Happen," to quit in order for his friend and fellow Teamster Robert Martini to get the business with his truck. When Christy refused Flynn threatened her equipment. Flynn told Martini that Christy would have to be killed or else people would "lose respect" for him. He told Martini that he should be the one to murder her since he would be the one to ultimately benefit from the deed. When George Cashman heard the plan he called Flynn to task and ordered him not to kill her but to send her a message. On August 15, 2000 while the movie was being shot Christy was attacked by Teamster Bartley Small. Christy reported the incident to the police but ultimately never filed charges.

Flynn is still currently under indictment by the United States federal government for racketeering.

As an actor Flynn can be seen in such films as Good Will Hunting, The Cider House Rules and What's the Worst that Could Happen?


Last edited by IrishHood on November 30th, 2006, 5:40 pm, edited 1 time in total.
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January 24th, 2006, 11:47 am #7



James "Spike" O'Toole was an Irish-American gangster from Dorchester, Massachusetts. He was a close friend of The Winter Hill Gang of Somerville, and their leader James "Buddy" McLean. He was targeted for assassination by The McLaughlin Brothers gang of Charlestown, when a Cambridge gangster named Ronald Dermody fell in love with his girlfriend. Dermody made a deal with George McLaughlin that if they would kill O'Toole, he would kill McLean. Dermody's plan backfired and he wound up dead, and The McLaughlin's forgot about O'Toole. Years later, in December of 1973, O'Toole (Who had survived many assassination attempts) was ran over by a gangland assassin while leaving a bar in South Boston.

Last edited by IrishHood on November 30th, 2006, 12:25 pm, edited 1 time in total.
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January 24th, 2006, 11:56 am #8



Ronald Dermody was an Irish-American gangster from Cambridge, Massachusetts and a member of Whitey Bulger's bank robbing team. Dermody, the son of gangster Joe Dermody, at some point in the early 1960s, made the mistake of falling in love with the girlfreind of Winter Hill Gang member James "Spike" O'Toole. So Dermody, despite his ties with the gang, made a deal with Charlestown mobster, and enemy of Winter Hill Gang leader James "Buddy" McLean, George McLaughlin. The deal was, if McLaughlin would take care of O'Toole, Dermody would do the same with McLean.

Unfortunatly, for Dermody, he agreed to kill McLean first. He took a shot at McLean, but missed, and Dermody went into hiding in Cambridge. He then called crooked FBI agent H. Paul Rico for help. Rico agreed to meet Dermody at the Watertown-Belmont line, a spot Rico picked, to discuss his problem. Rico then called one-time informant Buddy McLean and told him about the meeting. Dermody showed up to the meeting, as scheduled, and was met there by Buddy McLean who shot him dead on the spot.





Last edited by IrishHood on November 30th, 2006, 12:39 pm, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

January 24th, 2006, 2:14 pm #9



Francis P. Salemme, AKA "Cadillac Frank", was a prominent half Irish half Italian hitman for Boston's Winter Hill Gang during the 1960s. After serving time in prison from 1972 to 1989, he became the leader of the Patriarca crime family. He is currently in prison awaiting trial on perjury charges.

Salemme joined the Winter Hill Gang sometime around the mid to late 1950s, where he established himself as a leading hitman, along with Stephen Flemmi, during the Irish Mob Wars against the Charlestown Mob.

In 1969, Salemme fled the state after being indicted for attempted-murder, eluding capture by federal authorities until his arrest in New York City by FBI agent John Connolly in 1971[1]. Sentenced to seventeen years (although partner Steve Flemmi was not charged), Salemme was imprisoned from 1972 to 1989, then was released.

In January 1995, he was indicted on racketeering charges along with Whitey Bulger and Stephen Flemmi. Salemme was arrested in Fort Lauderdale, Florida and charged with racketeering, crossing state lines for criminal activity, extortion, conspiracy, and loansharking. He was convicted and sentenced to 11 years imprisonment. While serving his sentence, Salemme agreed to become a government informant and appeared before a Congressional committee shortly after his release in 2003.

Samemme was again arrested in November 2004 for perjury during a federal investigation regarding the 1993 murder of nightclub owner Steve Disarro, a charge for which he is currently awaiting trial.
Last edited by IrishHood on November 16th, 2006, 11:34 am, edited 1 time in total.
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Joined: April 15th, 2005, 9:58 am

November 16th, 2006, 11:58 am #10

New pictures added 16/12/06
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