The Underworld Podcast - Boston's Irish Mob Gang War: The Winter Hill Gang

Episode Date: April 7, 2026

In 1960s Boston, Buddy McLean ignited a savage gang war after tensions with the McLaughlin brothers boiled over into open bloodshed. What started as neighborhood beef turned into a cycle of ambushes, barroom executions, and street hits that terrorized Boston. McLean’s Winter Hill crew proved more organized and ruthless, picking off rivals and seizing control as bodies piled up. By the end, the McLaughlins were shattered, and the war set the stage for the rise of Whitey Bulger and the modern Boston mob. Learn more about your ad choices. Visit megaphone.fm/adchoices

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It's one of the few major cities in America where the Italian mafia isn't the dominant force, leaving room for others to ply their trade. Two of the others are the McClauchland gang from Charlestown and the Winter Hill gang from Somerville. Both are Irish, and they've been at war for the last few years. What started out as a drunken fight during Labor Day weekend in 1961 over someone disrespecting a woman has turned into an all-out gang war in the city of Boston and the surrounding suburbs. If you don't know Boston and have never seen an Affleck movie, Charlestown is a rough working-class Irish neighborhood just north of Boston's downtown. And Somerville is, or was, a rough working-class Irish neighborhood in the nearby suburbs. Think guys in fitted Red Sox hats with terrible fades and super thin line.

beards who love a good brawl. The Winter Hill gang, later made infamous by Whitey Bulger, takes their name from the neighborhood of Winter Hill, where they operate. They're led by a local street fighting legend by the name of James Buddy McClain. The McClauchland gang is led by three brothers, Bernie, George, and Edward, and in the summer of 1964, the momentum is on their side. A month earlier, they had taken out a top Winter Hill member, and now they had taken out. They had taken out of Winter Hill member, and now, they feel crazy enough to take another shot at McLean after several failed hits. But getting him won't be easy. He's legendarily tough and careful and beloved by everyone in Winter Hill.

On this particular day, McLean is jogging back from his workout at the YMCA, with a 38 revolver in his hand, as one does. As he runs around the corner of one block, he suddenly catches sight of the barrel of a gun pointing out a car window. Thinking quickly, he ducks down at the last. second as a bullet whizzes by his head, just missing him. McLean tries to run into a nearby club that his gang owns. But because it's Sunday, the side door is locked.

The car with the shooter chases him, closing in. But before they can get another shot off, McLean sprints by them and lets off three shots of his own, catching the shooter in the front seat right in the shoulder. The shooter fires back but can't hit McLean, who manages to run around to the front door of the club and make his way inside. He runs right to the bar where he knows there's a gun and ammunition stashed. He reloads and heads back out onto the street, a gun in each of his hands, only to find the

McClauchland hit squad had fled. McLean then goes to a different bar because, hey, it's Boston and he's Irish. What else are you going to do? He orders a drink and calls up one of his top lieutenants to come down to the bar immediately. The lieutenant arrives, and McLean tells him what happened, to which he says, quote, you can't live at home anymore. You have to have guys with you at all times. We have to get better organized and eliminate every fucking one of them.

We need another safe house. Get someone to look after your family. Give them plenty of money. Boston's first Irish gang war is about to ratchet up another level. This is the Underworld Podcast. Welcome back to the Underworld Podcast, a program about international organized crime, past, present, and future. From two journalists who have reported on this sort of stuff all over the world. or as we like to call it, cautionary tales from cautionary tales.

I'm one of your host, Danny Gold, and my co-host, your Amigo and mine, Sean Williams, who is now based in Buenos Aires, Argentina. And I think just got back from Paraguay, right? Sean, are you making new friends in Latin America? How are your tango skills? Yeah, I mean, I just got back from Paraguay, what, 10 minutes ago? Yeah. To let people be on the curtain a bit.

No tango skills, but my skills of, like, looking confused and saying pedodon is like, That is through the roof. So, uh, great accent. It's good time. Great accent on there. As, uh, as always, you guys can support us at patreon.com slash underworld podcast or on Spotify or iTunes. And I think even on YouTube now, you can buy merch like t-shirts at underworldpod.com. And you can email us, tips or advertising inquiries or anything else at the underworld

podcast at gmail.com. Honestly, Sean, I got no spark today, man. No witticisms. Winter's been too long. So let's just, let's get it going, man. I mean, I thought people were listening in for the ban. alone, actually. Some people like the ban.

I think a healthy amount of people do like the banter. I just got no banter right now. I'm just kind of tired. That's fine, man. Yeah. Tell a nice story. Okay.

Boston. Boston and its suburbs in the 1950s heading into the 1960s. It's a city caught between two worlds. You've got the old ethnic neighborhoods like Charlestown, South Boston, and the north end, still kind of humming with this tight-knit insularity

of immigrant generations where everybody knows everybody and loyalty to like your corner or your block or the city runs deeper than almost anything else. You're talking mostly Italian and Irish here, neighborhoods of dock workers and longshoremen, smoky barrooms, parish halls, and suburban Boston at that point,

it's starting to sprawl outwards towards towns like Somerville, Everett and Revere. Shout out to the dog track and Revere Beach, one of the worst beaches ever. They're filling up with working-class families looking for a little more space. But those suburbs never really leave the old neighborhood behind. The same allegiances, the same grudge

the same faces, just a few miles further from the water. Underneath the surface of all that blue collar respectability and kind of strict Catholicism, of course, is a parallel economy that's been running for decades. Bookmaking and numbers running, loan sharking, truck hijacking, union rackets, all the kind of Goodfellas classics that you see in the opening like 20 minutes of Goodfellas, right? The bookies and the gangsters, though, they're relatively low level, right? They're not shadowy figures to most people.

It's all very neighborhoody, right? not super violent besides kind of these street brawls and the occasional, you know, solid beating or murder. But these guys, they're part of the neighborhood, part of the fabric of everyone's lives. So let me get this straight. You managed to, like, if you managed to remain miserable and wintry, you're going to end up writing intros like that, like Dondolillo or something? Like, how do we make sure that you never see a ray of sunshine ever again?

You know, I tried to read Underworld and I gave up in like 25 pages. Maybe it's just not for me. I used to be able to finish any. Have you read it? I did the same when I was younger and I managed to redo it like a few years ago. It's awesome, but it's deep. Is it? Yeah.

What's the other one? What's the other one he wrote that I gave up on? Oh my God. Yeah, I can't remember now. God, I studied all this shit in uni. They just kind of bore me that these days, man. Like, I can't get through it. That's a shame.

But people love it. Anyway, by the early 1960s, the Boston underworld is nominally under the influence of of the New England mob, the Patriarcha crime family, operating at a Providence, Rhode Island. Raymond Patriarcha runs his empire with like a quiet cold deficiency, and Boston is a revenue stream that he kind of oversees and expects to remain orderly. But Boston is a difficult city to fully tame,

and Patriarcha doesn't have the men on the ground or the power to tame it fully, which is where you get these Irish crews, which are tough, territorial, and deeply skeptical of Italian authority, operating with a degree of independence that other cities would not not have tolerated. Like this sort of thing, 50s and 60s in New York, it was tough. You did have, like, the Westies and things like that, but no one operated at the major level that the Irish

crews in Boston were operating at. These groups, they pay tribute, they follow certain rules, but they're never fully absorbed or fully under the thumb of the Italians. And that tension, the kind of simmering for years beneath the surface, is like kind of kind of simmering for years beneath the surface is like kindling. It's ready to explode. I mean, I like the phrase Italian authority. It's just quite funny to the European ears, like pizza recies or football formations. I don't know. I mean, you know, I'm not talking about the Italian. You don't think that's funny to European ears, Italian authority and organized crime? Yeah, that's probably fair enough. I'll take back my comment about the Italian people. Enter James McLean, born in 1930 in Somerville,

Massachusetts. Shout out again to Davis Square. Terrible burritos, terrible pizza. His parents can't take care of him when he's born, so they give him up for adoption, but his real father still checks up on him once in a while. McLean gets the nickname Buddy because he's just a cute, well-behaved kid, and it sticks. Young Buddy gets the coveted job of crossing guard in his last year of elementary school because he's responsible and intelligent, and also all the other kids are terrified of him because he can beat the crap out of them and pretty much everyone else, even though he's like, 10 years old. He's like a brawler, a real Boston brawler. There's a story about him beating up a bunch of 16-year-olds when he's 11, just a fighter from the start. Buddy gets his first real job as a part-time

worker at a truck and company at the age of 13 during World War II, because all the older guys are all fighting, and that's just what you did back then. You got a job when you were 13. There were no iPads, no one's on Roblox. We used to raise kids right in this country. Ship them off to the mines, the warehouses as soon as their barmits of age, and guarantee you, if we did that now, Now, it would solve, like, pretty much all of Gen Z's issues. Yeah, but imagine how more efficient those child miners and chimney sweeps could have been if they just got that anxiety and ADD issues diagnosed. I mean, you ever think about that?

Did not think about that. Think about the industrial revolution with, like, you know, everyone's in therapy. That'd have been great. The children yearn for the mines. Everyone knows that. Buddy's an extremely hard worker, and everyone likes him. When he turns 17, his dad gets him a job as a longshoreman, which, for those who don't know, guy basically works at the docks.

In this case, East Boston and Charleston. Also, classic young mobster job. Buddy's a tough kid, but he gets pushed around by some of the hard-ass longshoremen, some of the older guys, so he starts working out intensely, and he gets really jacked and starts boxing. Soon enough, he picks a fight with the longshoreman who had kind of messed with him earlier,

and he just beats the hell out of all of them. What you're going to see is a constant theme in his life. After that beat down in front of everyone, buddy who is polite and kind of quiet by nature gets a ton of respect at the docks and nobody messes with him and his rep starts the spread. In 1948, he gets his first taste of the criminal life when he's leaving work and a dock worker hands him a box of Cuban cigars as a gift

which, you know, kind of fell off the back of a truck. Interestingly, not illegal then, right? It's pre-castero. He sells the cigars to a local shop and afterwards asked his dad who was connected down there what the deal was. Why did that guy give him the cigars? Bit of a naive kid, buddy. His dad fills him in on the fact that some of the dock workers they like to rip stuff off sometimes and sell it,

but warns him not to do it because he could get fired. Buddy, though, his mind is already racing. He gets together a few dock worker buds, including childhood friend Howie Winter, and they start stealing from the docks. They start out by stealing some kind of select choice merchandise and storing it in a warehouse where they know the owners. Buddy's calling the shots, he's the mastermind,

and around the same time, he gets married and starts having kids. You reckon this guy would have made millions as an influence? He's like getting shredded. He's violent. He's boxing, brash. He's smoking cigars. Like, I'm seeing dollar signs, man. You know, done well.

You know, here's the thing. I actually, from learning about him, he actually seems like a pretty stand-up guy besides obviously organized crime. So I don't think he would have been an efficient influencer in that regard. Okay. You know? The gangster with too many morals for Instagram. He does come across, like, someone who has like a sort of stand-up guy quality to him.

You know, the sort of old-school. gangster that usually it's a lie, you know, usually they're all scumbags, but he might break them all, to be honest with you. Interesting. So he's still fighting in the streets sometimes, but he starts having this aura of being this legendary street fighter. In the book, Love and Feared Buddy McLean, there's a story about a cop visiting four guys in the hospital trying to find out why they were all beaten up badly. And it turns out they picked a fight with Buddy, and the cop is shocked to hear one guy did all that damage. He even gets the reputation as being the toughest guy around, just like Rocco de Mayo in Essex County, Sean.

The jacket. There we go. Yeah, I was waiting for you to, it's been a while. Yeah, we need to throw one in there. But I mean, that's perfect. It's the toughest guy around. Since you mentioned, yeah. The jacket.

He gets such a badass reputation that people from all over the area come to fight him. Local boxers, other tough guys, all types of challengers. And on Friday nights at this one bar, Buddy would post up welcoming anyone who wants to throw down, which sounds like a movie. but apparently the dude could just fight really well. He would sometimes have five to six fights in a night, just dropping people left and right, which by the way,

you know, when you read about these, like the Monk Eastman story or boxing rounds in like the 20s and 30s, and they're like, fights were like 25 rounds? Yeah. Was it just,

were people's skin and bones just tougher than? Were people hitting a lot lighter? Were the gloves like 47 ounces? Or was it all just exaggerated? It went around 47 seconds. I thought like, I thought they were basically hitting, with, I think they were basically hitting with gloves that were made out of concrete as well,

weren't they? So they just sort of rearranging. I read something once that actually, that like bare-knuckle fighting in the old days were actually less dangerous because you don't get the kind of CTE hits that way. You would have got like your face smashed about, but it wasn't as kind of like brain chugging. I don't know. Maybe that's right. Maybe I dreamt that. I mean, I'll all of that up at one of these points, but I'd rather, I want the mystery to sort of persist in my head. It can hang over everyone's next two seconds until they'll get up here. So he and his friends, they just hang at this one bar and people would come from all over to the triumph. And apparently he wasn't a jerk about it. He wasn't like picking fights or being a bully.

It was more like an athletic competition. He's actually, he becomes like a beloved figure in the neighborhood, known for being a nice guy and extremely polite, not some thug who just goes around beating people up for fun. There are also stories of him doing things like paying for someone's rent when they were about to be convicted, hunting down some neighborhood youths who jackalate his purse when she gets robbed, leaving church, you know, that sort of stuff. Yeah, okay, fair enough.

He's not an influencer. You probably have to, like, kick the homeless person or something like that. Yeah. No, he seems, by all accounts, stand-up dude. Just endless stories of this type of chivalrous behavior while also beating people off. Very Yining Yang.

In another story, he walks in on an armored robbery, sorry, armed robbery of a liquor store where there's a cop who's actually one of the customers in there getting, robbed and while the gum in our mask, buddy basically tells them he knows who they are and they need to stop it and return the money. And they do. He old school, like I said, old school in that way, trying to keep crimes like that down in his neighborhood. And he actually earns the respect of the Somerville police. And in turn, the cops basically look the other way on his dock robberies

and truck hijackings. He starts doing with his crew. He's basically become a local legend. At one of his favorite bars, they actually keep his preferred bar still empty just in case he comes in, which is how I think, Sean, that was your story in the nightclubs in Berlin, right? They kept the bathroom stall completely empty for you. No? The c-stall. Yeah. No, not the c-stall that you sit on.

I meant the bathroom stall that you go. But yeah, that works too. They kept the cubs stall. Yeah, yeah. Someone got mad at me for continuing to make the Berlin jokes. And one of the commenters making fun of you too much. Oh, they're coming out to bat for me. Yeah, coming out for you.

Yeah. They're tired of me, giving you a hard time. but little do they know that this is one of the sort of things you developed in Berlin. You like being, you know, insulted and yelled, right? Does that play into it further? Yeah, I mean, the stall. Exhibit A. His fighting a general demeanor earned him real celebrity status.

People would like gathering a crowd and just watch him work out outside. So I guess that is sort of influencer-like, right? He's working out. People are just watching him do it. I was going to say, I love that you don't even need. to say, I'm actually going to talk about this other guy now, because you've just mentioned me sitting in a cup chair in a club, and then this guy is sort of like beating people up, which is clearly not me, and people like him.

I don't know, dude, I've seen you on the pitch. You get, you know, got wide shoulders. You can get aggressive when you need to be. Yeah, well, yeah, I'm in Buenos Aires now, so I'm getting the shit kicked out of me. Wow, are they, I thought, I would assume Argentinians are like finesse players. Is that not right? No. They have both. They're mad. They have the Italian break your legs challenges, kicking off, but they also dive and they're like really theatrical. It's quite annoying, actually, to play with. Yeah, but you're a proper Englishman. You could be the enforcer. Yeah, but then they realize I'm an Englishman and it makes them even more mad.

Oh, yeah, I forgot. Yeah, well, that stuff. I can't even say the name because then, yeah, don't do it. Not yet. Paul, not yet. We've got to get ads in our, for art and skating steakhouses. By the mid-1950s, buddies hijacking takes more of a good fellow's vibe. You know, Jimmy the gent, he has the driver's on the take. So, Looks like a hijacking, but really the drivers are in on it, and they get some cash too. And he does all this while remaining a longshoreman and a Teamster, so he simply sits in on the local Teamster meetings where they discuss what shipments are coming in, and he takes notes of what he and his crew can steal. Then he contacts various buyers to see if there's any interest in the goods. And one of those buyers just happens to be Raymond Patriarcher from Rhode Island, the boss of the Patriarcher Crime family, the main Italian mob family in New England, which I always thought was weird.

I mean, Providence is a very mobbed up place. I think we've talked about Buddy Sianz. Before, the greatest mayor in the history of America. But I always found it weird that, like, the group overseeing Boston, which is pretty sure a bigger city with a lot more money coming through it, was based out of Rhode Island. Even though I guess the docs, a lot of stuff came in through Providence. But, yeah. Yeah, I mean, talk about getting cut. Like the whole of Massachusetts getting cut by Rhode Island.

We're starting rivalries that people just don't even know. In 1957, one of buddies guys flees town because he's a suspect in a bunch of robberies. He's also keeping a book and loan sharking and he sets up McLean to take it over. Within a few months, McLean triples the business while sending half the profits to his buddy on the run. While all this is going on, the McLaughan gang is on the rise and starts making their presence known. This is a gang led by three brothers with their base in Charlestown, aka Ben Affleckville. Or Casey, Affleckville in general. If you've ever seen a Affleck Brothers movie, it's probably based in Charlestown.

There's five brothers originally, but two of them die in World War II, and from a young age, they get up to shenanigans. Robberies, assaulting people. In the book, Boston Mob by Mark Sondini, he quotes a local cop describing them as low animal-like cheap thieves and petty shoplifters. They just paint a picture. One of the brothers gets arrested for the first time in what would be 30-acre arrests at the age of eight for trying to steal oranges. Such a like throwback thing. But what happens when you, an eight-year-old steals oranges? What do you do with them?

Do they go to detention of some kind of special place for kids? Like, what happens? I don't know. It's also weird to cite that as like one of it, because that's, you know, stealing bread out of the mouth of decadence, Sean. I don't know. I'm not going to quote that song again, more. But I feel like that's sort of crime that you understand, like, the kids like eight years old and starving that he's going to steal.

We need some vitamin C. I mean, scurvy was still around back then, I assume. But, uh, anyway, bad guys. guy, bad brothers, they do bad things. Another one of the brothers, Edward, whose name is punchy because he's a boxer. Side note, was anyone in working class Boston back then, not a boxer?

I'm pretty sure everyone at some point was a boxer in Boston. He eventually starts working at the Charlestown Docks with his brother Bernie, becoming a labor organizer because in the 1950s, if you're a criminal looking to up your game and the organized part of that, that's just what you do.

And his brothers, they soon build up a loan sharking and gambling operation right at the dogs. They also managed to hook up with the Genovese crime family in New York, and they serve as their muscle in Boston when it comes to union disputes. Now, whereas Buddy would mostly fight with people who were looking for a fight and was also like a nice guy who would do charity and stuff like that, the McLaughlin brothers and their gang are cut from a different cloth. They enjoy the violence. They don't mind inflicting it on random people. Other criminals are scared of them, according to a mid-1950s FBI report. And unlike Buddy and his gang, the McClocklands aren't opposed to murder. They would do

contract hits for the New England mob, the patriarch of crime family, and sometimes they would just kill people over random disputes. For example, one time a union member threatens to revoke their longshoreman cards after they beat the crap out of a different union guy. So in response, they kill the union member who threatened them. They're sort of the quintessential, like new younger thugs, doing away with the old respectful ways of doing things, you know, that sort of old trope and organized crime. Working outside in the springtime, you know, you're dealing with chilly mornings, hot afternoons, everything in between. It's really hard to get one pair of pants that can keep you situated with all that. Not to mention you got mud, rain, whatever else the weather decides

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only at Yamava Resort and Casino, celebrating its 40th anniversary. You win? Must be 21 to enter. Yeah, they're not nice at all. Speaking of Troyes, do I tell you the story of my one trip to Boston? Like a few years ago? No, you did not, and I'm looking forward to more lore.

Oh, yeah, it was great. I did an in-flight mag story back in the good old days of in-flight mag stories, and they sent me out from Boston to Berlin to Boston, which is pretty sweet. And then I've got an entire penthouse floor of a hotel, which Jay-Z had just stayed in like a couple of days before. And then I made a map of all the most notorious dive bars in Boston, because idiot. And then I just did a crawl around him.

I ended up in this place that was genuinely like scary. And it had a guy who was propping up the bar and he'd been an official in Chalcestu's Romania. And I think he was like saying that someone else in the bar like another Romanian wanted to kill him or something. Anyway, I'm pretty sure that bar was in this Charlestown place. And like, yeah, sometimes you do got to hand it to Boston. And that place was rough, like way rough. And this was in like 2015. So, yeah, I probably wouldn't do that these days.

I think it's genderfied a bit. What was the story on? It was really cool. It was just about like the islands, all the islands that you can visit on little boats and stuff just off the bay or is it the harbor? I don't really know. And someone just took me on a boat. And it was a nice sunny day.

And I was like, okay, I went on a boat. And that was the story. That's it. God, I loved In-flight Mags, man. COVID. Anyway, yeah, so during the 1950s, it was nice. I liked hearing about it. I want to read that story.

During the 1950s, we talked about Buddy's taken over this gambling operation from his buddy, and he's growing it. And at one point, a bunch of bookmakers who were aligned under some Italian gangsters operating under the Patriarcher family, they start getting threatened by the McLaughlins. Instead of switching over to the McLaughlins, the bookmakers decide just to realign themselves with Buddy and his crew. The Italians are pissed, but they know Buddy isn't a pusher. and they know he does business with their boss,

Patriarcha, down at the docks. So they decide it's best to have a sit down first. Buddy tells them at this meeting that if they leave Somerville to McLean and his guys, he won't try to encroach on any of their territory. The Italians, they're pissed off at first, but Buddy says lays it out to them like, you're not properly backing the bookmakers

in Somerville versus the McLaughlins. Someone needs to deal with them, and we will. To which one of the Italian says, quote, you want to deal with those fucking animals, which, like we said, notorious at that point. Buddy says that he will and also says that it'll help provide muscle for the Italians if someone isn't paying their debts

in Boston and the surrounding area. He also offers a bunch of other stuff, like laying off the big bets they get on the Italian bookmakers, saying he'll work with them on hijackings and selling goods. And the Italians accept figuring it's actually a pretty good deal

since they don't have the muscle to do battle with the McLaughlin's and Buddy's crew at that moment. So Buddy's expanding, getting into more than just hijacking, stealing from the docks and running a few local books. This is going to be the foundation for the Winter Hill gang, which is the name the press eventually comes up with for Buddy and his crew because they hang out in the Winter Hill neighborhood of Somerville.

McLean further expands when high-profile gangster's not associated with either McLaughlin's or the Italians come looking for his help after hearing about his deal with the Italians. Buddy sticks to his deal with the Italian mob, doesn't get directly involved outside of Somerville, but he tells them they can hire his friends to help with collections with the deal being that they get a 50% cut, and a few of the gangsters, they take up his offer.

Buddy's deck collection methods are actually pretty different from what you would think, right? His guys are polite but firm. They try to work out payment plans. They use Buddy's feared reputation as this sort of implied threat of violence, which I kind of feel like is a lot of how deck collection works. Anyway, more of the like, I'm disappointed in you,

then I'm going to break your leg strategy. And I mean, you can easily see the difference, right, between the McLaughlins and the Winter Hill gang and how things are shaping up. The McLaughlin's, by all accounts, are just deranged. But Buddy and his gang, even though, you know, buddies's a vastly different character, they still get along with the McLaughlins,

and they would drink and party together. Because even though, you know, buddy's a different type of cat, they still had a lot of things in common, basically being criminals, beating people up in street fights, and being Irish, and drinking. In 1960, the McClauchlands even tried to get Buddy and his gang to team up with them to push out the Italians, but McLean declines,

saying he made a deal with the Italian. Italian sustained in Somerville, and it's just easier to work together. And if they did attempt to push out the Italians, it might work, but they would probably lose. I guess the elephant in the room here for me is, like, are we into Whitey-Bolger era? Boston, I forget when he starts coming into play. No. He's in jail for a lot of this. I talk about it later on.

He really doesn't sort of emerge, I think, until the early 70s as like the bit player. But he does end up taking – he's in a different gang, too. Those two gangs, that's the second Irish-Mab war. they fight, they get absorbed into the Winter Hill Gang and that's when Whitey Bulger takes over as boss for the Winter Hill Gang which I think is in the early to mid-70s but that's another potential out. I mean Whitey Bullger, I didn't want to do that

because it's just like two, you know, there's so many movies made about him, there's so much stuff on him. Yeah, I mean, I remember I got into him a bit because there was the time when he tried to take over Higher Life. It's kind of like gone into the movie as well, right? The Black Rath or whatever it is. And that was a kind of interesting one. do, but yeah, I think he's, yeah, he's done.

But yeah, so these two gangs, they hang out. And one Labor Day weekend in 1961, Buddy, George McLaughlin, one of the brothers, and a bunch of other goons are partying together in the coastal town of Salisbury, which is located right where Massachusetts and New Hampshire meat. George McLaughlin is a notorious drunk, and it's Labor Day, so, you know, the guy is most likely toasted beyond belief. Early on the weekend, on Saturday, George says something rude to a young woman, and Buddy, being who he is, gets in George's face.

George, there was a punch at Buddy who promptly just beats the hell out of him. No one at the party really thinks much of it. It's typical Labor Day weekend, Irish Goon Squad festivities. It happens. They fight each other. People get drunk and brawl. But George doesn't take too kindly to it.

He goes over to a local bar and starts talking trash about buddy loudly where someone McLean's squad is actually kind of hanging out. He follows that up by mouthing off to another young woman and again catches another beating, two on the same day. but he's not finished yet. He returns to the cottage he's splitting

with two McLean Associates and their wives starts talking trash to one of the wives. The husband goes after McLaughlin who stabs him with a broken whiskey bottle. Then the other McClain associate gets involved and they beat him sentencedless, then dump him in an alley, leaving him for dead,

assuming someone would just think he got hit by a car or something. But a passerby finds him, brings him to the hospital with a broken skull and only two remaining teeth. He's in critical condition for two weeks, but he survives. And the other McClainty,

Clockland brothers, they somehow find out what happened immediately. And Bernie McLaughlin goes hunting for the two McClain associates, who have fled town and iron hiding. So Bernie, who's the leader of the McLaughlin, goes to see Buddy at his house about giving up his two friends. McLean tells Bernie, he's not going to give them up, that his brother George got what was coming to him. The McLaughlins are pissed.

They're not going to let it die. Soon after, Bernie and Punching McLaughlin go pay visit to Howie Winter, who I mentioned earlier, also kind of funny, like his name is Howie Winter, it's the Winter. Hill Gang, but it's not named after him. I don't know. Just, uh, just interesting. Maybe. Sean, no?

Yes? Not interesting? Five out of ten. Okay. Howie is McLean's childhood friend and is generally viewed as the number two in the Winter Hill Gang. They demand Winter give up the location of the two Winter Hill gang members, but like Buddy, he refuses.

The McClocklands, they're not used to people saying no to them. A little over a month later on October 30th, 1961, buddy is at home when his dog starts barking like crazy. grabs his gun and goes outside and sees several goons moving around his car. Fires a bunch of shots at them. They scatter away, running into a waiting car. The following morning, his neighbor looks over and see something's wrong with Buddy's car. The hood is up and there's something dangling from under the passenger side of the car.

When the neighbor looks closer, he sees dynamite attached and then calls the cops. Cops shows up, who just happens to be friends with Buddy and after inspecting the car, he tells Buddy someone was trying to put a car bomb on his ride, which I feel like you don't need a cop to tell you that if there's got a bunch of guys fiddling around your car and there's dynamite obviously visible. Like, I feel like I could come to that conclusion. But he tells the cop not to call it in that he's going to handle it himself. Yeah. I mean, this feels more like a threat than a serious attempt. Like, leaving a stick of dynamite just dangling from the hood of a car like he's the roadrunner or something. What's going

on? I think they were trying to lay a bomb for it, and they just didn't have time, right? Oh, okay. Okay. I was thinking that they've just hung it like some kind of weird threat. Yeah, All right, that makes more sense. That day, Halloween, 1961, Buddy and an associate go looking for the McLaughlin's and catch Bernie outside a bar where he's making a collection. Buddy puts five bullets in him from close range, and when cops arrive on the scene and find the die McClockland,

asking who shot him, he refuses to say. You know, some nice old-school, Murta, and he isn't even Italian. When Buddy goes to tell his inner circle about the hit, they all agree that now the McLaughlins won't stop until the Winthor Hill gang are all dead. A few days later, buddy and his associates get picked up for the murder

due to an eyewitness. An interesting note about the associate. He was a low-level guy in the Winter Hill gang. He was basically the driver for the hit. But after the incident, he does a short sit in jail for a different matter and actually moves to California and McLean's urging to get out of his life

and change his name to Alex Rocco. He changes his name to Alex Rocco to become an actor and he later plays Mo Green into Godfather who was based on Mo Dallet, who I eventually want to do an episode on. So that's a little fun fact right there. Pretty crazy. That's better than the last one.

You could definitely get half an hour down the pub out of that one. Yeah, I mean, it's pretty, I mean, you know, Mo Green, one of the best, man. The Mo Green special. Anyway, buddy and the eventual Mo Green get hell without bond, but the case gets dropped a few months later due to the lack of evidence because the witness changes their mind. By 1962, there is full-on gang warfare in the streets of Boston between the Winter Hill gang gang and the McLaughlin brothers, which also becomes known as the Charleston mob. And the gang war becomes known as the first Irish mob war of Boston.

The second Irish mob war, like I said, a decade. later, that's going to lead to the emergence of Whitey Bulger as the boss of the Winter Hill gang. But this one, because Charlestown and Somerville actually board each other, it's almost like a neighborhood civil war, you know? There's a dividing line between the two areas. You have a bunch of people who are connected through either family or marriage or long-time friendship, basically having to pick sides. And some people are actually forced to move houses across the dividing line. Wow, Irish guys find each other in rival neighborhoods. I've never heard of such a thing. Just in case, I'll add a disclaimer, just in case anyone's listening in their Irish or they're uncomfortable with that comment, it's okay. Don't worry, I can say this because I'm English.

That's true. And you do, you actually do, you know, use a lot or save a lot of your scoring for England itself too. So I feel like you can get away with that sort of stuff, you know? I thought you were going to say, and you do do a really good Irish accent, at which point we would have moved swiftly on. Do you? I do have an Irish name. No, absolutely not. I can do it. I can do an Ian Paisley, but that's for another time. We'll get to it. So all these businesses, too, that operating neighborhoods, legitimate ones, and criminal ones, they suffer during the feud because, you know, people aren't hiding. They're going out with, like, hit squads, everyone's got bodyguards. To ensure loyalty on his end, Buddy would have someone on his team followed by an observer for a few days

and write every observation down. It's very stasi-like behavior. But effective. He would then hand the notes to whoever was the subject of the tail as sort of been an implied threat to keep people on their toes. Buddy's crew takes an early loss when in April of 1962. He gets sentenced to two years in prison for a previous unrelated fight, but he continues to run his gang behind bars and actually uses his time in prison to recruit new members.

In July of 62, a Somerville friend of the McClauchan's turns up dead with a bullet in his head. In September, a McLaughlin brother finds Howard Winter's car and puts a bomb in it. A woman actually borrows the car from winter, and after she parks it exits, the bomb explodes 24 hours after it was placed. I guess these were like old school car bombs that go off on a timer because of instead of ignition. I'm not really sure how that worked.

kind of a dumb way to hit someone. But yeah, this sort of vary out in the open public warring. At this point in Boston's gang war history, it's kind of unheard of since prohibition ended. Maybe between Chinatown gangs, but not like this among like, you know, the Irish and Italian gangs of Boston. McClauchlands also tried to take out McLean while he's in prison,

but he beats the brakes off two attackers and sends them both to the hospital. Yeah, I mean, that's not surprising. Imagine getting the audio that you're going to take down the guy who literally does public workouts and is known for basically beating up everyone he's ever met since he was 10 years old.

I wouldn't take that job. Toughest guy in the neighborhood. One of the people that buddy recruits in prison is a guy by the name of Joe the Animal Barbosa, which is a top-tier nickname for an underworld guy. Good. The animal is a renowned hitman for the Italian mob, but not an official member

because he's Portuguese and not Italian. He's actually annoyed with the Italians and kind of blames them for him being in prison in the first place, so he views himself as more of a free agent. He's also a former pro boxer, just like everyone else, already with a notorious reputation, a real psycho where one story has him literally biting a man to death over a late payment. In prison, yeah, Buddy persuades him to join the Winter Hill gang along with a few underlings

he has working for him. Buddy gets out of prison in May 1963, and as soon as he's out, McClauchin send people to Winter Hill to see if they can get a clean shot at him. They report back to the brothers that not only are there a ton of people around him, making an attempt very hard, but there are kind of. cops all over, almost like they're waiting for an attack. Later in the summer of 1963, but he goes back to work at the docks, which are located in Charlestown,

like the center of enemy territory, which it's insane that he's still working this job and also insane that he'll do it in the stronghold of the gang trying to kill him. It's so crazy that even the Boston police chief calls the head of the Somerville police chief to be like, keep your boy out of Charlestown. Yeah, I mean, this is when like rising growing culture was actually cool, right? He's like, what, pulling a nine to five, he's got a family, and he's a dangerous criminal. It's like that guy who says he works at six hour days or whatever is, like, I'm going to kill you. You have work, I work one week, I'm going to kill you.

It's like, yeah, but he just does supplements, winges and sort of goes down the gym or does software development, right? You really? This guy is like, this guy is a legend. What's going on with your algorithm, bud? You're really on this today. I just, I love that video. I've watched that video so many times. Oh, the guy who I have four days and.

one day, that guy? He's like, yeah, I do three days, six hour days. Yeah, it's a classic. A month, do you do a month? I've done three months. Yeah, it's awesome. That's a classic of the genre. McLaughlin's guy spot him walking alone at one point, but don't feel they have the right

guns on them to take him out since it's just a chance sighting. Remember, they are not the only guys in Charlestown with a gun. Five days after that sighting, a gang member does have the right gun at him when he's buddy, takes a shot at him and misses so badly that the Winter Hill gang start calling him Ray Charles. But the Winter Hill gang does take him. take the incident seriously enough that they tell McLean, he has to have bodyguards around him when he's in enemy territory and he reluctantly agrees. The next major event in the war comes when a top

Winter Hill member gets caught by the McLaughins in the summer of 1964. This gang member, he's got to hustle with a partner where they would extort rich guys who are cheating on their wives with hookers in Florida. Not sure of the mechanics of how that works, but okay, you know. I'm guessing sexy lady camera, maybe. I don't know. Yeah, but getting the Boston guys down there seems tough. The partner sells out the winner Hill guy and sets him up for the McLaughens to grab, they handcuff him, they drive him to a dirt road, then they kill him. It's a big blow to the organization.

And then shortly after that, that's where we get the cold open and the attempted hit on McLean that fails. He actually goes into hiding after it and Howie Winter is placed in charge of the business aspects. Buddy then gets a tip from a very unlikely place, the FBI. But if you know your history of Boston organized crime, it doesn't seem that unlikely. The feds had apparently been investigating the McLaughans for some time and were not big fans of them. pretty easy to see why law enforcement would choose buddy over the brothers. Now, this particularly FBI agent, Paul Rico, who one journalist will later call perhaps the most corrupt FBI agent in history, gets into all types of shenanigans. But pause for a second, there's no way he's even the most corrupt FBI agent helping the Winter Hill Gang, let alone in history because basically 10 or so years later, FBI agent John Connolly will infamously spend decades protecting and helping mob boss Whitey Bulger, who coincidentally took over his boss of the Winter

Hill gang in the late 70s, so not in the earlier mid-70s. Now, the reason this corrupt FBI agent decides to side with the Winter Hill gang is because he hears the McClellan Brothers call him and Jay Edgar Hoover Finoics on it in legal wiretap. Seriously, that's the entire reason of what it was, but we are talking about Boston in the 60s, so I'm pretty sure most people in the neighborhood who find out about this would probably be like, yeah, yeah, that makes sense. That's a legit reason for the FBI to try to get you killed. But anyway, the tip is about a top person in the McClauchin organization, who just happens to be one of the shooters from the cold open. And basically, the Fed tells McLean the location of a hooker who this guy frequently visits.

And the next time he goes to visit this hooker with another McLaughlin, and two of his people are waiting for them inside the apartment. They grab them, they torture the guys, they interrogate them, before killing them and dumping their bodies in the Boston Harbor to send a message, which is what we do when you need to send a message you're not to be trifle with. Isn't it, Sean? Just dumping shit in the harbor. Yeah, it's also really important to distinguish that from taking a dump in the harbor.

I mean, if you do that, they might not let you back into New Zealand. Or anyway, I mean, it's just a hyper-taic. Still illegal. Yeah. Still, we've tried to get that repeal, but it's still legal. How many discounts does USAA auto insurance offer? Too many to say here. Multi-vehicle discount.

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Go listen to Morning Cup of Murder wherever you get. your podcasts. And remember, stay safe. The interrogation works out. They find out that the two remaining McClaughton brothers have weekly meets on Monday mornings in front of various police stations as a sort of protection from attack.

And they also find out that the McClaughton brothers have a spy in Somerville that only they know the identity of. That's kind of like the departed, right? That sort of secret spy and the other organization thing. But I guess the part is more police and gangsters,

but you guys, you get it. When the bodies are discovered in the harbor, it's intimidating enough that a few McClaughton guys actually decide to switch sides. They reach out to Buddy, they tell him that the McLaughlins are actually on the run with some of their top guys, not staying in Charlestown anymore.

And if the Winter Hill gang wanted to make a move, now is the time to do so. Buddy wastes no time. He actually catches one of the McLaughlin's top lieutenants in Charleston outside the guy's apartment, but he actually lets the guy go because he's with his kid. He warns the guy, next time he catches him, he's dead,

and tells him that he and McLaughlin should just quit the war, quit the game, and leave Boston. Spoilers, spoiler alert, this is very, um, ends up being very Carlito's way, but you'll see what happens at the end. The Winter Hill gang at this point is looking like they're going to finish this thing off. And in yet another blow,

George McClockan gets drunk at a christening and kills a random civilian and gets put on the FBI's 10 most wanted list and goes on the run. McCleckins are just not nice guys, man. You can see why they'd want Buddy and his crew to be in charge. Basically, it's a wrap, right? November in 1964,

the hit squad catches punching McCaukeland off guard when they find him outside of Boston Hospital alone. There's an assassin dressed up as a rabbi. Yep, a rabbi, like it's a Guy Ritchie movie, catches him, shoots him in the face, but he survives the initial shot, and smartly runs back into the hospital, but not before being shot in the back.

He ends up surviving, but losing a part of his jaw and getting a collapse long. But also, I feel like Hasidic Jew in South Boston is not a great disguise in the 1960s. And that's usually what people, like, when they say, rabbi, they mean Hasidic Jew. But personally, I would have gone, with priest, but to each their own.

Yeah, maybe it boils down to hats. Who's got a cool hat? It's a pretty good showdown. Has seed or priest. They're both pretty cool hats. I'll see it's get some sick hat. If it's cold weather and the fur one, the strymol's in it. Big fur one.

Incredible hats, yeah. A few months later in early 1965, George McClauchin finally gets arrested. And the guy who brings him in is that corrupt FBI agent. He originally planned to kill him and then plant a gun on him, which is just what you did back then, but changes his mind at the last second. Now punchy despite being close to mortally wounded is still in hiding, moving from location and location on Cape Cod.

McLean sends the Italian mafia hitman, the animal Barbosa to find him and kill him, takes him a while, but he finally tracks him down, the Winter Hill Gang lays an ambush, they wait to see him drive by, they unload on him, they hit him three times, but he speeds away and drives himself to the hospital and again somehow survives.

This guy either won't die or the Winter Hill Gang just can't shoot people for shit. this time, Punchy's hand has to be amputated. He's basically got like no body parts left at this point. It does make his nickname way funnier, though. Yeah, yeah, it definitely does. McClaught and gang, by this point, falling apart, their loan sharking and gambling operations are collapsing.

Their guys are scared to go to collect debts, and McLean is also telling people who owe them money not to pay. They don't have to worry about the McLaughlin's, and even though everyone thinks they're finished and his crew is excited, McLean tells his people it's not over until all the McLaughlin's are in the ground. Although it sounds like the only one left is basically crippled So I don't know man

I feel like you won In the fall of that year in 1965 Buddy figures out what bus stop Punchy takes to catch the bus To go to his brother George's murder trial Which why are you taking the bus Like if you're in a gang war And you're taking the bus

You've lost that gang war You're not in the gang war anymore You should give up Throw in the towel Get an email job And just it's donezo for you Now they want to send a shooter That Punchy doesn't know

And they decide on an up-and-coming gangster By the name of Stephen Fulner Flemy. The reason I even mentioned his name is because I imagine a lot of you are familiar with Whitey Bulger and Stephen Flemy ends up becoming one of his top guys and also an FBI informant for like 20 years who is now serving life in prison. But October 21st, 1965, Flemmy walks behind Punching McClauchland as he's getting on the bus, shoots him twice in the back of the head, and when Punchy turns around, he shot five more times and finally dies. The first Irish gang war in Boston, as it's known, basically ends that day and the McClauchan group

is eviscerated. Or is it? Because remember that guy that McCawken lets live? Because he's with his kid. Him and like one other guy are still around. They asked Buddy for a truce and Buddy says no. I think also incredibly funny that he shoots him twice in the head and the guy goes, huh? It just turns around. It's amazing. Rumors spread that the remaining two guys skipped town. But less than two weeks later, Buddy's out with two of his bodyguards doing collections when that guy who McLean let live comes out of nowhere and pops him with a shotgun, killing him. It is a wild ending to a gang war that was supposedly over.

Nobody wins this one really, right? The temporarily triumphant buddy at 35 is dead, killed at the last second, just a real buzzer-beater, you know? There's a lesson there, Sean. I'm not sure what it is. What is it? I'm going to say that whenever you complain about things happening today, just read literally any story from the 60s, and it was probably a lot worse back then. Yeah. That would do.

Yeah. Yeah. 2,000 people attend Buddy's Wake. The Winter Hill Gang, though, they power on. The Animal Barbosa tracks that guy down, and the only other one of the two remaining McLaughlin gang guys takes them both out. There's a couple other, I guess, remaining high-level guys who flee,

but the remaining lower-level ones are actually incorporated into the Winter buddy's childhood friend and number two, Howie Winter, takes over as the gang's leader. He becomes known as sort of a diplomatic, pragmatic leader and really tries to consolidate the Irish underworld while maintaining good ties with the patriarchy crime family. In 1972, Winter mediates and ends a gang war between two other smallish-irish gangs called I think the Killeen and Mullen gangs.

That gang war had been raging for several years. It's known as Boston's second Irish mob war. And Winter, with the help of the Patriarch of Crime family, steps in to end it. Both of those smaller surviving gang members basically joined the Winter Hill gang and settle the beef. And one of those surviving members is Whitey Bulger. Bulger had been in jail for most of the Winter Hill, McLaugh in Gang War, only being paroled in 1965. Bulger, who actually becomes an FBI informant in 1971,

because the Boston FBI office, like we said, corrupt as hell, works himself high enough in the organization that when Winter and several other gang leaders get sent to jail in 1971 for fixing horse races, he actually takes over, and the rest is history. Yeah, I'll just say that this is actually a better show than the rest is history fact. But yeah, that was a great story, man.

Really interesting. Much better. Yeah, I stumbled a bit with it, guys. Both Sean and I were up very early this morning and had a lot of technical difficulties. I can't even see him right now. We're doing this old school. So I hope you guys enjoyed it.

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