The Underworld Podcast - The First Gangster Kingpin of New York

Episode Date: February 17, 2026

Monk Eastman ruled the depraved streets of turn-of-the-century Manhattan with fists and absolutely zero regard for human life, commanding an army of 1,200 thugs who terrorized the Lower East Side. At the height of his power, he was pulling cash from every racket you could think of while rigging elections for Tammany Hall and overseeing street violence so extreme that cops needed reinforcements just to enter his territory. Eastman represented a true transition in the evolution of the underworld, when crime became organized. All that, and he managed to become a war hero too, before the street life finally caught up with him. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Hasbro is not a sponsor of this promotion. November 1903 in an abandoned barn on the outskirts of the Bronx. A gang war is brewing on the streets of downtown Manhattan between the two most powerful men in New York City. It's actually almost like a real war, because both men have thousands of soldiers underneath them, and when they clash on the streets, there are pitch battles that can last all night. What's happening here, though, is actually an attempt to stave off those battles. Because election season, when the two men put aside their differences and used their street soldiers to help get the corrupt politicians that protect them elected, has just ended.

And there's trouble brewing over some territory. Very profitable territory. You see, there's about to be a boxing match in this barn, one that all the politicians and high-up police officials have basically begged the two men to have. Because the two men in the center of this dirt ring, in the middle of nowhere, surrounded by hay bales are Monk Eastman and Paul Kelly. And instead of sending their two gangs to battle it out all over the streets in New York, they've agreed to settle it man-to-man, king-pin to kingpin, in the ring, the victor claiming the disputed territory they've been fighting over for years.

That territory has New York City's barry as its center point, the city's red light district. This is the days of the East and West Village being depraved like none other. It makes the 1970s and 1990s look like Switzerland. It's a time of unimaginable poverty in New York and the violence and pain and crime that go with it. Brothels on every corner, drunks laying dead in the gutter, thieves, hustles, cons, opium dents, bar brawls every night that end with corpses, Tenement buildings packed with entire families living in a single room, rampant diseases, rat and dogfight pits. It's a place where life is cheap and only the strong survive. And Monk Eastman is perhaps the strongest and the most feared.

Before him, the gangs in New York were mostly violent street brawlers who did some crime on the side. There was no organization, no organized crime. Monk changed that, professionalized it in a way. He took over territory, ran the rackets, got in bed with politicians and police, consolidated other small gangs. You want a business in his territory, pay up. You want to do crimes in downtown New York?

He needs a taste. Only after him, when Prohibition hits, do the real mafia's really emerge in New York. He represents this powerful transition period in the evolution of New York City's underworld. By the early 1900s, his Eastman gang had become more than a gang. It's a brutal empire.

Eastman himself was a walking mystery. read a biography of him, quote, he was undoubtedly a gangster, a bruiser, a burglar, a thief, a liar, a thug for hire, a pimp, an opium peddler, but he covered his track so well that even the most basic facts of his existence were open to question.

Which brings us to the boxing match. Each man is allowed to bring 50 of his own guys in the crowd, and every gambler and respectable criminal in New York worth of money in his pocket came to watch, drinking bottles of wine, smoking cigars, and bedding heavily. A referee from a neutral gang oversees the rules. Rounds don't end on a timer. Only when someone goes down.

Only if you can't make it back to the center of the ring, it's over. Monk is a real brawler who earned his name knocking out anyone who came his way. Kelly's smaller, but he had been a professional boxer and had recently beaten the hell at a monk's right-hand man, a monster heavyweight, in a different one-on-one brawl. The men end up fighting for over an hour, each one going down a few times, but no winner is declared.

A noble effort, but the war continues on. This is the Underworld podcast. Welcome back to the Underworld podcast. An audio-visual experience where every week, two journalists that have reported on this stuff all across the world, on the ground, take you on a journey through international, organized crime, past, present, and sometimes future.

I'm one of your host, Danny Gold, recording here at Spotify Studios in New York. I trade off hosting duties every other week with magazine writer and reformed Berlin party boy Sean Williams who was joining us from his living room in New Zealand lots of new listeners this week and you know hang out

listen to a few episodes write nice things about us in the comments look past the fact that I'm wearing sunglasses indoors it's bright lights big city over here isn't it the depths of winter over there is that sunglasses weather? Yeah but that's like a book I was making a literary reference so people know that oh my god sorry

But no, it is the depth. We read books. Dude, it's like, it's like 12 degrees and snow. It's just, it's very depressing. And, um, anyway, moving on. As always, you can get bonus episodes at patreon.com slash anewel podcast and ad free. You can also sign up directly on Spotify or iTunes. Help us keep the show going and pay for Sean's impending move to Latin America.

Well, he'll be trying to figure out how we can help launder money for import export companies through said Patreon. Yes. What else? merch at UnderworldPod.com. Email us, tips, or whatever else at the Underworld Podcast at Gmail.com. And oh, yeah, shout out to Righteous Felon's Beef Jerky. They heard me talking about Bill Tong and Beef Jerky last week, and they just sent me a whole bunch. So, I don't know. What else, Sean?

What should we talk about? Japanese denim, expensive jackets. Anything else? I don't know. Fast cars. Yeah. Like a good mortgage. Yeah.

I don't know. Yeah, reach out. Okay. So to really understand Monkees, man, we need to dive into the world he operated in and came from. It's actually really fascinating. You know, I love reading and learning about the New York City of that era, 1880s, 1890s, 1900s.

It's a wild, wild time. I mean, I love the gritty New York City crime history stuff. We've done so many episodes on various time periods and eras and the crime organizations that went with them. But this one, I mean, this is like, I think the first place I heard of Monkeesman was reading Herbert Asby, gangs in New York, which actually came out in 1928 and details that period and it is just dark. Like if you think things were grim in the 70s or the crack era, it's kind of nothing compared

to how violent and degenerate things were back then. Anyway, fantastic read. Read that and Low Life by Luke Sante about early New York crime days. They're just both fascinating books. In gangs in New York, there's a few pages that dive into Mongeisman, and they talk about him being the first real gang boss and having thousands of soldiers at his disposal. And the main book for this episode, The Main Source, is called The Heroic Gangster by Neil Hanson, which is a biography of Eastman.

Okay. New York of the 1890s, early 1900s, it's a city in the throes of massive transformation. It's experiencing immigration on a scale that's really hard for us to understand today. Between 1880 and 1920, over 23 million immigrants come to the U.S. and a huge proportion of them passed through New York City and many of them stay. Yeah, every time you do a New York episode from this era, I think, I don't know, maybe the folks who skipped on

and got there like 1,000 acres in Kansas or Iowa did pretty well, actually. It's going to be deprivation, right? This is going to be the hallmark of this one. Like, Dickensian is like not even close, does not capture what downtown Manhattan was like in those days, as we're about to learn. So the ethnic makeup of the Lower East Side, which Monk rules over at this time, was incredibly diverse and constantly shifting.

There'd been a lot of Irish that'd settled in the number four. You know, that was when I think the, when was the potato famine? Around that period, no? Yeah, like a little before. Yeah, yeah. So they'd come over earlier, and they were a bit more established. But during that time period, 1870s, 1880s, 1890s, you had a whole lot of Jewish immigrants from Eastern Europe, Russia that were arriving,

fleeing pogroms and persecution. and you had a whole lot of Southern Italians, a lot of Sicilians, fleeing poverty. And the Lower East Side of Manhattan, for those who don't know, that's like, you know, the East Village, Tompkins Square Park, in later years, punk rock, everything cool New York that comes out of there.

Any gangster movie based in the 20s and 30s talks about it. That's where, like, you get the Yiddish and the Italian accents, clothes hanging from a clothes line between apartment buildings, push cart peddlers, kids in newsboy caps. You guys know what I'm talking about. Yeah, imagine if you will, a young Sean Williams too in a Sonic Youth t-shirt heading across Tompkins Square Park to get chili sauce for the for the Puerto Rican abuelas for some reason living in in

in the alphabet city it was a it's great times and I'm sure like quite the image of coolness just to just kind of ram home this idea that it is a really great part of town did you have someone take a photo of you posing in front of the Joe Strummer mural that was right there I mean, I'm sure I did that like 10,000 times, yeah, but nothing survives from that era, thank God. There are almost no pictures of me in New York, which is great, actually. I would recommend that for any young children, thinking of spending their entire lives in front of a camera. Yeah, don't, don't, don't do any of that. Okay, so during this period, it's one of, if not the most densely populated places on earth, and it's just incredibly poor.

I mean, you know the jokes about Manhattan apartments being the size of closets? Back then, it's whole families with, like, 10 children living in them in these squalid tenement buildings, barely any sanitation, diseases are running rampant, very little running water, coal-burning fires, and these things, like, regularly burnt down. You had people who barely saw sunlight, sweatshops where people are working 16-hour days, six days a week, and not just men, but, like, women and children in these death-trap factories. And there's basically no social services or anything provided by the government. You had do-gooders, soup kitchens, churches and things like that,

but it was mostly everyone for themselves. And it was vicious. So you had crushing poverty, no safety net, no police really. And I mean, there were police, but they were really inept, understaffed, and horribly corrupt. Sounds like it's changed a lot. I mean, you joke, but like compared to what it was, it's just, it's insane. So these places, they're chock full of crime and just vicious violence everywhere,

gambling dens, brothels, pre-teen prostitution. the seedyest saloons and dance halls, the kind of places that had like rat pits where men would bet on rat fights or dog versus rat fights or dog fights. Or dog and mat, like, on rat on mat. Oh, wait a minute, hear me out. Rat on rat on rat on dog.

That would be one. I mean, I think that's what they were. It was like multiple rats versus like a terrier, like a rat terrier. And they would, dude, it's very unpleasant. On town, it sounds great. So garbage, like you had garbage lining the streets.

Even worse than it is now, where it's just garbage bags piled up in New York because, you know. But then you had to like wade through it. Rats everywhere, smell. The trains were overhead, you know, so the noise, push carts, rotting food, drunks passed out, being robbed, being murdered. It was just ruthless. Everyone's a predator. Crime and corruption everywhere. Okay, so I think, am I overdoing it?

I think we can call it. Yeah, I mean, yeah, I think it's quite bad, right? It's what you're trying to say. Yeah, yeah, it's what I'm saying. It was an very unpleasant place. So this is the world Monke Eastman is born into in 1873 or 1875

and his real name is Edward Eastman I think there were a couple of things that they said maybe his name was Edward Ostroman or whatever it was but Edward Easterman is his name and you'll see that a lot of details with him are murky. He later gets the nickname Monk short for Monkey

and it was because he climbed everywhere when he was doing burglaries up drain pipes, fire escapes, walls, fences all that stuff. Like I said, Details with him are murky. He has like 12 aliases. The cops don't even know his real name or his age at most situations, most points when they arrest him. No one is sure of how many kids he has or wives, for that matter.

The guy liked to tell a tale. And not only that, the newspapers back then, they weren't big on fact-checking. So a lot of competing info on this guy. Even his background. Most reports put him as Jewish, the son of recent immigrants, which makes sense, considering he operated in the very Jewish Lower East Side, and his Eastman gang, was predominantly Jewish. There was a report or two that has him as Irish as well,

but according to heroic gangster, which looks to be the most solid info on him, he was neither, and his heritage was most likely English generations back. I guess, like, Eastman could be a Jewish name, right? It sounds like it would be, I don't know. Like, that's very interesting. He kind of predates the period,

but it's the rise of Italian and Jewish organized crime. And Eastman definitely sounds more Jewish than Italian. But you'll see people change their names, like the main Italian gangster at that time gives himself an Irish name to avoid the stigmatism that comes with being Italian which if you're Italian and you give yourself an Irish name

that's got to be like ultimate betrayal right there, dude. Yeah. Also, according to many reports, contrary to what people say, he's not born into poverty, but a lower middle class family. His father is a wallpaper hanger,

which I guess is the job back then, and his parents split up when he's young. And he spends most of his youth or some of his youth on the uppery side, eventually ending up across the river in Williamsburg, Brooklyn, in the late 1880s. He's not one for school, but he's a wealthy relative

who sets him up with a pet store when he turned 17. Monk is big with animals. He likes to walk around holding a kitten, and he also had a trained blue pigeon that sat on his shoulder. Oh, so he's just like a late 90s Cohen brother's character then.

Yeah, I got it. I mean, in the Q-O-Mond once, he kind of is. Like, he could be a gangster in one of their movies when he's not, like, viciously beating the crap out of people. Big Bird guy. Big bird guy, especially pigeons, which also Mike Tyson, another New York City brawler. Legend has it that Tyson first got into a fight or first got noted for his fighting abilities because somebody in Brownsville killed one of his pigeons on purpose, and then Tyson just like absolutely wrecked the guy who was like older and bigger than him.

And Monk, by this age 1617, he is Tyson-like. Guy is a gift for beating the hell out of people. And he's short like Tyson. He's only 5'7, though apparently most gangsters back then are like 5'1. I guess because of, like I assume malnutrition, right? Monk, though, he's like, he's stout. He's built like a brick. He's built for violence.

He's got pug face, cauliflower ears, like only a brawling 1890s gangsters could have. His face is eventually, like, marked by scars and just batterings. He'll have gold front teeth, but not because he has a sick grill, but because his teeth had been broken in fights. Did you guys actually know that Sean used to always wear a grill out back in like the little John days, diamonds, everything? This is, I mean, Sean had a. really wild 20s that we don't talk about enough.

Yeah, that's right. It's sad but true. I mean, Sonic Youth Tea, Chili sauce, leather harness, grills. Am I doing it right? Is there any, am I missed anything? Do I need like hard drugs as well, something like that? Do you still have it? I mean, you could put it on for one of the episodes. It would look good. Oh my God. Well, yeah, okay, let's go for it. Then I'll just get grills. Why not?

Yeah, that's another thing. You could spot to the show. Like any of those guys on 47 studio have the Instagram accounts? Any grills companies? Send us grills. If you're in a way, what do they sell grills though? Houston, send us grills. Sean will wear them on an episode. You could put your company name across the, anyway.

You get the bill tone and I'm going to wear grills. What a great pair of men. Spitz is going on too long. I'm not doing good work. Monk is just, he's a rough looking guy. And actually, apparently a lot of the early TV shows and movies over the next few decades, the gangsters and hulums for a lot of them are based on Monk Eastman, down to the way they talk and they look.

And if you look at a photo of him, you will see why. Yeah, the guy, that guy is not a looker. I'm definitely sticking with the Cohen brothers finger. He's striking. Like, he's scary looking. Yeah, yeah, yeah. Great of a brawler, dude. No stranger to the street.

He opens up this pet shop and he uses it as a front to sell stolen pigeons. I guess back in those days, young kids in poor neighborhoods would catch or steal them to sell, which not that I think about it, there's like a little minor plot point in the wire with that when them catching pitches, right? You know, people kept flocks back there. Was it for messaging? I don't really know. Either way, he has his hustle. He's also always stealing, doing some breaking anterings, brawling.

It sounds a bit like the early scenes in Once Upon a Time in America. I don't know if you've seen that, but like 30 years earlier. He chooses the life, though, which again, major misconception. I always assumed he was a slum kid. At some point, around 1892, he realizes the money's in Manhattan, and he moves back over the bridge at the age of 18. He settles in the Lower East Side and, you know, well, I describe the neighborhood up top. But to add to that, quoting the book,

The poor lived and died in crowded, crowded festering tenements, and the most basic human needs, fresh air, clean water, even daylight, were hard to come by. Sounds like these guys just need a whole food and the heaps to burger joint. They're going to be fine. Little sunlight. Little sunlight never hurt anyone.

And as soon as Monk gets there, a depression hits, and it gets worse. Quote, for many inhabitants of the Lower East Side, the only employment was rag-picking, begging, theft or prostitution. So this is the world that he becomes an adult in, right? And he takes to it very well. He's well known to the police soon enough. His first arrest is for stealing pigeons, which, you know, that was his hustle. He spends nights in jail here or there, but in 1898, he's bagged for carrying burglary tools and spends three months locked up. He finds work when he gets out as a bouncer at the infamous silver dollar saloon where the owner was connected to Tammany Hall.

Do we know, like as Tammany Hall, the people know what that is, especially not a Americans? I don't know. I don't know. I mean, I'm thinking of Jim Broadbent with a big side of burns from the movie, but I don't really know it beyond that. It's basically a byword for political corruption, but I'll go into it a little bit more later in this episode. So that bar, it's across from the courthouse, which I used to hang out in a courthouse bar when I was reporting. They're cool places. Not as cool as they were back then. Yeah, they're good. Yeah. This is the headquarters for like scumbag lawyers, corrupt judges, bail bondsmen, fake witnesses, corrupt cops where you could arrange things to pull one over on the legal system.

There was influence to be had there, and Monk, he starts getting it, right? And this is when he starts to understand the organized part of organized crime, how to work the system and how to get it to work for you. I kind of like the old days, right, when there's like bars were headquarters for things like that, right, that you had this gang there. There was a bar of like all guys who did arson, stuff like that. So he soon moves on to another bar where he beats up the bouncers to get his job. And this bar is famous for robberies and rapes,

which is way less fun than being the headquarters of scammers. This is a dance hall, which they had back then. And during that period in that neighborhood, most danceholes are basically brothels. They were live sex at stage, they were drunk in brawls, and the women often pickpocket the male customers. Criminals, pimps, prostitutes, thieves, basically like the apartment of a young Sean Williams in Berlin.

There we go. Some of these dance... That's one. Two, one? He's a bit late on this one. He hasn't mentioned it so far. Yeah. Well, we got, there's more time.

Some of these dances they throw, they're massive. And, you know, it's a seedy, seedy criminal element. So Monk needs to keep watch with the crew of hooligans. He carries a weighted club, brass knuckles, and a blackjack for just knocking people out. I mean, this is like, it's like the Deadwood era, but for New York City, you know? That's essentially what it was. It was deadwood, but like in the most packed environment you could think of. He's what they call the dance hall sheriff.

And he beat enough people. up that it really establishes his rep on the lower side. Bouncers were like a very, like everyone needed them. All the bars, the dance halls, the gambling dens, they all need protection. And being a bouncer, it's like a really heralded thing back then, necessary for all businesses. And the people who get noticed are basically like superhuman brawlers. See, there's a lot of gangs back then. But there aren't really any like, like, mafia's. Nothing's organized. Like, there's no organized, organized crime. It's very Wild West. It's definitely nothing like you're going to see. 25 years later when Prohibition hits.

These gangs are fluid, they're chaotic, sometimes forming alliances, sometimes warring over territory, but they're basically like guys who like fighting the streets, like have rumbles out there with all sorts of like melee weapons, right? They're part army, part thieves guild, part community enforcers.

They sell a little bit of protection, they collect debts, and sometimes they commit acts of theft or violence simply to kind of like establish or maintain their reputation. And reputation then is everything. A name carries weight. And Mongeisman, he's beginning to carry enormous weight.

Oh man, very right. And you went on Don Winslow then. It's like, so is this the era when the Sicilian mustache pizza coming over from the Costa Nostola that, we did that episode, it was last week, right? Are they coming over like formalizing stuff turning things into a proper mafia?

Is this, does that come slightly after this then? Where are we in that kind of? I mean, the Italians definitely had that in their neighborhood, but that comes like 10 or 15 years later. Monkeys really like this, I'll get into it, He's like this transition in crime going from like these like brawler gangs to more organized. He's like the middle step in the evolution.

So those guys will come around 1915, some like that. Arnold Rawsteen's around them too. He's like, obviously a big step up in terms of organization. He generally gets the credit, I think, for being like the real first organized, organized crime guy in New York. But then, of course, prohibition is what, 1920? And that's when everything changes. All right, guys, a quick break from smugglers, Kingpins. and highly organized crime

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lets you filter hotels by neighborhood, vibe, star level, and amenities like pools and spas and beach fronts and wait, I'm not done. Stop cutting the other. Price line! No? So Monk, though he is this transition period and he starts building slowly, right? Some fights, some rumbles,

establishing his territory. He's a natural born leader. People throughout his career as a boss, they're not only drawn to him, but they're loyal to him. People like him. People start joining up under him, and he's sharp, right? He starts recruiting a lot of youngsters from the poor Russian and Polish Jews that had recently settled in the neighborhood. Immigrant parents kind of lament at what their children are turning into, but it also creates a form of protection. Writes Hansen, quote, Monks gang also provided what might be described as a public

service by protecting the Jewish population of the East Side from the depredations of attacks of Italian and Irish gangs, often operating with a tacit consent encouragement and sometimes active participation of New York's predominantly Irish police force. Like I said, this is like a turning point in New York's gangland scene, which up until then had been dominated by the Irish, who came over in prior waves. Now you've got Italians and Jews coming in at higher rates, moving into the salams, and this is when the first, the Italians and then Jewish organized crime start to take over in the lead-up to prohibition, which is when they explode and when organized crime becomes organized crime.

There's still Irish crime, like organized crime for certain. You know, these guys are active during Prohibition, even up until like the Westies and the 70s. But this is when you have Lucky Luciano and Frank Costello teaming up with Meyer Lansky and Bugsy Seagull, the Purple Gang, all that. Monk is like a transition piece on the way there. So how kind of deep mafia core is this guy exactly like? Would most folks in NYC recognize the name or is his history kind of been buried

somewhat over the years? Because I don't know much about it. I mean, I'd never really heard about him at all. And what I guess I'm really asking you is how many conversations can we have off the back of this show with like LA film guys that go nowhere? That's the real question. First of all, calling something mafia core is very, it's going to appeal to our Gen Z audience that we need to grow. I don't think too many people know about him unless they read gangs in New York or like have really looked into early crime days. He's not a well-known, I mean, definitely not like Lansky or Costello or Bugs you see him.

He's not, I wouldn't say he's under the radar, but he's not well-known at all from like your sort of average listener, I would say, or average person who looks into this sort of stuff. So Monk is getting together a gang of young pickpockets who he sends all over the city into rich neighborhoods. He's basically codifying the extortion protection racket for businesses. And he's also making any criminal trying to operate in his territory pay tribute. He's got big-time thieves going out, lockpickers, safe crackers, people running brothels, all that. he's taking in cash, and his gang starts growing in wealth, power, and influence.

He's got lieutenants by his side he delegates to, though he's not against getting into a scrap himself for remind everyone who he is or doing some dirty work. Most gang leaders of that era, they're just kind of like

the toughest guy in a group of tough guys. Monk is that, but he's also like an organizational genius. His gang becomes known as the Eastmans, and they hurt so many people that the local ambulance drivers refer to the nearby Bellevue Hospital

as the Eastman Pavilion. Yeah, I mean, if you look at a guy, he just looks like a thumb so you wouldn't i mean i wouldn't want to go anywhere near a fight with the guy especially if he's holding what a weight a weighted club and brass knuckles jesus christ yeah the old school like melee weapons they fought with were uh definitely definitely interesting at this point right he's gathering up all the other small gangs on the east side and putting them under his umbrella forming a massive organization unlike the small improvised crews of his youth this is like a formidable organization right they control the

territory, a lot of it. In New York City, hundreds of thousands of people live under their area. They do the usual rackets I've talked about. They also get big on doing violence for commission, like an earlier iteration of murder ink, but a lot more beatdowns instead of murders. Even politicians start commissioning them for violence, and they start taking notice that Monk is a guy you both need and want on your side. And that means he soon links up with Tamney Hall. So Tamney Hall is also known as the Society of St. Tammany. It's the Democratic Party political machine that controls New York City politics from the 1790s through like the 1960s with varying degrees of power. But its golden age is like the 1850s up until the 1920s, 1930s, right when

kind of Monk's reign is smack in the middle. And Tammany Hall, like I said, it's a byword for political corruption. And what it means is that really what they did is they understand that political power comes from controlling votes. And controlling votes doesn't mean doing policies that people like. It means using whatever means necessary to get those votes at the poll and make sure that your opponent doesn't get their votes. So that means, first off, when New York City and the massive immigrant population coming in, you provide services to them, help them with problems,

get jobs, navigate the bureaucracy, even getting soup kitchens going, all with the understanding that their vote is now yours. And so all wet and good right there, that's, you know, politics. That's sort of the nice part, right? Yeah, that is nice part. It sounds like democracy in action. It's good.

Yeah. But the other side of that, that the gangster side is violence to get those votes out, right? Violence to stop the other side from getting their votes out. Massive election fraud from stuffing ballot boxes, getting people to vote five times in the same election, intimidation to prevent opposition voters. I mean, these are the days of a guy voting,

then going to a barber to shave his beard off and leave a mustache, then voting again, then going back to the barber to shave the stash, then voting again. This is what you do at craps tables, right? After I get banned, yeah. You don't get banned for losing all the time. So it's a misconception there. You only get banned from winning, so I've never had to deal with actually getting banned from any sort of gamble.

They actually like it when you lose a lot. That's their goal. Damn. You know, so, yeah. Never going to get banned over here. I do have a calcium bet right now. Oh, God, go on. No, you know what?

We're not going to, I'm not giving free advertising anymore. No, come on. Come on. Come on. No, no, no. No more, dude. It's on whether a politician says something at a press conference. I've got to stop doing that, dude.

Oh, my God. I'll stop. I've got to stop. Anyway, there is massive, massive, massive. corruption, outright stealing and embezzling to political favors. You know, they're buying votes to maintain that power, which they then used to enrich themselves through like the normal graft, kickbacks, patronage, and just stealing, like blade up stealing from the city treasury. Everything's cashbacked then. You just take it. The police are controlled by Tammany Hall, the firemen are

controlled, the judges are appointed by Tammy Hall, the district attorneys, hell the juries are most of the time. They control everything. So if you're with them, you're untouchable, and you'll win your election to. And they need gangsters like Monk, not just to get the votes out of the people they control in their territory, but also for the dirty work I just talked about. Uh, RIP Norm, we miss you. Anytime I see dirty work, I just think of like a norm, man. Um, they get paid and they get political production. Monk does. Charges dropped, police looking the other way, just complete immunity. Monk and his gang are their muscle, and Monk understands the importance of their patronage like no other gangster before him had. Him and his higher reps at this point, like I said,

they can do what they want. They're arrested dozens of times, often like serious stuff, right? Assault wants for murder, but he nearly always gets off. By the time the 1900s arrive, right? 1901, 1902, Monk has 1,900 men in his gang

with some reports saying 2,000. He even has junior gangs, right? Like the junior east men's, like the farm team. They start as young as 8, and he can recruit from them. You know, they're like going out doing their little pickpocket schemes. He's got all sorts of people employed under him.

every sort of criminal you could think of leg breakers, killers, pamps, hookers, thieves, pickpockets, they basically control the entire east side of downtown Manhattan, including at that time, New York's Red Light District, which it had, which doesn't have anymore, his headquarters is at a dive bar right there. I mean, this is like, this is just better than Instagram drill kids and scammers, isn't it? It's cool. Like, just hanging out of bar, not on Instagram, just, I don't know, man, not a care in the world, not online, just violence up close.

personal like it's supposed to be. It's a glory days, man. We really missed him. It really is. Monk and his crew are living quite good, too. Quote, Monks Rise heralded the emergence of large-scale organized crime and a federations of criminal gangs uniting

to further their interest or defend their territories. He was the bridge between the era when the Irish gangs have been dominant and the emergence of the mafia and organized crime as we know it today. And he's professionalizing, too, as this goes on, right? He's got the lawyers on retainer, constant meetings with politicians. He's the preeminent gangster in New York City at this point.

The Prince of Thugs is what they call him, which is great nickname. Nice. It's also said that Monk is one of the first gangsters to get involved in the labor rackets starting in 1897 when he beats up two leaders of a protest ring. And he soon starts getting work

both from the unions to beat up scabs and the bosses to beat up the strikers. This is the days of like the garment industry operating all over Manhattan, sweatshops and whatnot. I think we actually went into the way gangsters got involved with unions and labors in an episode.

I can't remember which was the murderink one. It's a good one. Yeah, I think so. Yeah. And my next one on Japan is going to get deep into that as well. It's like the bread and butter, right, for loads of organized crime back then.

Dude, that Japan one is so good. Guys, tune in for that. I think it's, it might have happened before this. It's so interesting. So if you didn't listen to it, go back. Oh, okay.

Yeah, we're doing it all backwards. But it's, yeah, definitely do it. And go back and listen to the murder rink one if you want more in-depth stuff. on the labor union rackets and all that. Soon enough, Monk is doing work for the upper class, for the big deal private citizens, right? He even links up with an up-and-coming,

18-year-old gangster by the name of Arnold Ralstein to help with his loan sharking business. One of his lieutenants is also Big Jack Zellig, who I might need to do an episode on. He is a very famous gangster. He has a menu at this point for hurting people like Murder Inc did. You shoot someone in the leg, it's $1 to $25, arm $5 to $25, $1 to $50, murder.

10 to $100. High-quality scriptic podcast. How much of that cost? Probably around the same price, to be honest with you. Yeah, probably the same price as a lake. Monk is not uncontested, right? He does have a rival, someone competing over the Bowery with him. That's the big area where the Red Light District is.

His name is Paul Kelly, who despite the Irish name, is actually an Italian guy who leads a predominantly Italian gang known as the Five Pointers, who operate at the Five Points of the Bowery, which is where these five main streets come together in downtown New York was basically America's biggest

Red Light District at the time and it also becomes like a very famous area of the five points in that period and later on the Bowery too it gets known for like

just a you know I think poverty and degradation and punk rock and all that and the 70s and 80s and everything but at this point

and for decades later it's an infamous gangster area in New York City for generations that's when the Bowery gains its rep as like some sort of combination of Bourbon Street

the Las Vegas Strip and Amsterdam's Rite Light District except for very, very poor people. Women, girls, gross dye bars, cocaine bars apparently at the time, and definitely in the 90s, opium dens, psychics, carny-type circus stuff,

cock fights, rat fights, dog pits, gambling dens, tattoo parlors, shooting galleries, everyone on a hustle and a scam, beggars, peddlers, con men, the days of, like, rolling drunks, picking pockets, robbing tourists, shanghing people,

fresh bodies in the gutter every night. Just a modern day germore is what they call it and what it sounds like. Kelly is born in Italy in 1876. His name is Paolo Antonini Vaccarelli, which honestly sounds a lot better than Paul Kelly. I don't know why he changed it. If he was alive right now,

he would most likely have like a Yankees tattoo on his calf, maybe earn a good living as an influencer talking in an exaggerated Bronx accent while making the same joke over and over again talking about sandwiches. But he lived in different times, right? He starts off working in Italian bank, actually. he's a bit of a lethario,

which actually earns him a few beatings because he, you know, sleeps to other guys' girls, which makes him learn how to fight and he becomes a professional boxer. He links up with some other young, by the way, great, great narrative to tell if you're a professional boxer,

like you're being interviewed at a fight, and they're like, what's your, you know, origin story, sort of like, I was just, I was getting with too many guys' girls and they kept beating me up, so I thought of, I'm going to imagine, be a great thing to say,

even make that up if you're a professional boxer right now. So he links up with some other boxers and he starts Kelly's five, points gang. They take over the five points area from the Irish Dead Rabbits gang made famous by the gangs in New York movie. Well, famous now, they were also very famous 100 years ago. So was the movie based on like a completely, like the narrative was true or were the names of the gangs true but the story completely made up? The story is completely made up, but like the atmosphere, the name of the gangs, the sort of back and forth, I think is all very true.

It's based on the book, but the book doesn't have like, it has narratives, but not really like that, you know? I think there was a bill. Was Daniel DeLuisse's character real? like that big cutting guy? I believe he was. I believe the barber character. I haven't seen it in a long time. I believe the barber character was real as well. I don't know.

Like, obviously the details in the narrative are like fiction. But it's like historical fiction. It's such a good movie. Kelly's different than Monk, right? Monk looks like a thug. Tresses like one. And Kelly is like slick, suave, handsome. He's a dandy.

Very opposite of the roughneck monkeys, man. He speaks four languages, talk about fine art, it's charming. He runs a flashy dance hall where actually some of the uptown elite come to get their kicks and go slumming. Interestingly, in his gang, there's a couple of youngsters coming up under him that go on to be the most powerful gangsters in America, like Charles Lucky Luciano, who sold heroin and morphine under his protection,

and briefly Al Capone, because Al Capone was from New York first. So Kelly and Monk are the most powerful gang leaders in New York, probably the country, and they fight a bitter rivalry over the areas in central downtown Manhattan with their territories sort of come up against each other. Kelly's got the West Side, Eastman, the East Side, and they're fighting over the Bowery and the spoils from all that D-Gen stuff. Though, during election season,

they actually work together because they both support and benefit from the same politicians with Tammany. So they regular fight over territory, but things kick off for real in April of 1901 when two five-pointed gang members strolled into a ball where a monk is drinking and shoot at him.

They miss him, but they chase him into the street where they yell that he's a thief, so a crowd kind of converges on him. Then they run up and shoot him in the stomach twice. He gets up, plug the holes with his fingers, plugs the hole with his fingers and walks to it nearby hospital.

He's not expected to make it, right? The lying New York Times even reports that he's dead, but after being a critical condition for weeks, he pulls through. At first thinking he was going to die, he actually names his attackers, but once he realizes he's going to live, he recants and refused to testify

because, you know, gangsters code. But also, what's the thing, like during this period, it seems like everyone's getting shot all the time and surviving, even though the hospitals must have been terrible? Like, were the bullets just a lot weaker? I mean, I assume they had to have been, right? just the guns were weaker, the calibers.

I think they were all like massive cannons, weren't they? They were probably just inaccurate. People getting shot in the leg and the arm and shit. But I don't know. Let us know in the emails. Yeah, there's got to be gun guys out there who know this stuff because I do not. He gets out of the hospital and a week later, a woman lures a five-pints member out of a bar only for him to be killed in the street.

No one is charged, but the police end up telling everyone that monk got his man, one of the men who targeted him. Now, both Monk and Kelly at this time, they're basically sending out roving packs of their hooligans with the instructions who attack any rival they saw on site. In September of 1902, there are full-scale battles on the street as it spirals out of control.

Packs of like 60 armed men hunting gang members. I mean, these guys are going out by the dozens, like rolling deep, looking for fights. Monk is also fighting a war against the Irish Yakey Yakes, another small gang. There are nightly pitched battles. Police are pretty much powerless to stop it. They're usually outnumbered.

They don't even have the same weapons that these guys do. And even when they arrest them, no one is willing to testify. Only when things really spiral do the bosses at Tammy Hall summoned both Monk and Kelly to them to tell them and knock it off for a bit and make them sign a peace treaty, and then they have some sort of party for the communities down on. But it only lasts for a little while, and then they're both back to doing raids,

they go into each other's bars and dance halls, they bust them up. One night they have something called a Battle of Ribbing, Street, where 100 gang members are shooting at each other for hours and hours, chasing the cops away, while guys on rooftops are doing airmail, throwing down bricks onto whoever is down there. After the Rivington battle, things get so bad, they organize another treaty, but the police commissioner actually steps in and does a bunch of raids, even claiming to have shut down the Paul Kelly Association. Although at the funeral the next day for one of his men killed in the Battle of Rillington, he shows up with a parade of 2,000 soldiers. The commissioner then goes after the Eastman's two. He arrests a noted 15-year-old Sicilian girl. known as the bride who was so violent she had risen near the top of these men's.

This all happens, of course, during elections. Oh, that's right. The woman with the teeth in Gangston, New York, she's based on a real person too. You know, the one who had filed her teeth. Was that Cameron Diaz or something? In the show? Is she the one who, I don't know if she, I think she's, there's a female gangman. I haven't seen

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Free shipping and 365-day returns. Quince.com slash underworld. Don't forget the underworld. Let's support these guys. Have a good one. This all happens, of course, during the election season, October, November of 1903. As soon as the election season ends, though, they get right back to attacking each other, and that's when we get that brawl in the cold open that does not end with the declared victor.

But in 1904, Monk runs into some bad luck. First, he gets locked up in Jersey. He'd actually, this guy who was called the Wolf of Wall Street back then, maybe the first. He hires Monk to threaten some guy who was going to testify against him in an assault case. Monk beats the hell out of the guy in front of a police station. No idea, you know, why if he's the boss, he's doing these sort of jobs, but maybe the payday was solid. But he gets arrested, and the victim says he's willing to testify. The police are desperate to get him on anything.

He actually gets picked up in New York City. There's a whole big extradition thing with having him send out the Jersey to face trial. It's a big circus. Monk's politicians are attacking the guy testifying, and the police are so scared to keep holding him in New York City, they eventually transform over to the county jail in Jersey where they hire a ton of extra security. Meanwhile, Monk does the goodfellist cooking scene in jail.

He's only held for 10 days and let out on bail. By the time the trial rolls around, he had state senators testifying for him. Eventually he gets found not guilty, goes back to Lowery Side, throws the big party, actually leaves the city for a bit for things to cool off. But alas, he could not. not stop doing penny-ante stuff. Maybe he just loved the game too much, you know? A few months later,

it's three in the morning one night, and Monk and a pal are in the fancier part of Manhattan, when they see a guy come out of the bar looking rich, looking drunk, looking like a target, flashing a lot of cash. They also see two thug-looking guys near him figuring, you know, these guys are thieves like us. They're waiting to make their move, but let's move on this guy first, you know, sort of like moving on the vipers when they're heisting wine. So they step up to the guy to rob him, but it turns out the guy's lurking, they're not thieves. They're Pinkertons, private detectives, almost like mercenaries in America at this point.

They're actually there to protect the drunk who happens to be the wayward son of a very wealthy and powerful guy who hired them to protect his Sean Williams-esque son. Look, I mean, I'll take a lot of abuse, but you're really going to start a fight with a guy in a leather harness with grills holding chili sauce. Like, no, there's no security required there, son.

I mean, they did. It was a huge mistake because the Pinkerton men, they immediately opened fire, shooting at Marlowe's. Monk and his partner who fired back, run out of ammo, take off running, a nearby car sees the commotion. Monk doesn't see him. He ends up catching him blindside with a nightstick, like, you know, that sort of... Wow, that's fully out of the movie. Yeah, that's what I'm saying.

I mean, that's how it's described in the papers. So they arrest him, they throw him in jail. This time, though, he's kind of screwed, right? The Pinkertons can't be bought, although I guess they kind of can be bought, right? That's their whole thing. In this case, they can't be bought or messed with by corrupt officials, like a regular cop, apparently. They're seen as incorruptible.

Even Tamney Hall cannot help at this point. Monk ends up staying locked up in the city jail for a month until trial, where he gets found not guilty for attempted murder, but guilty of assault and sentenced to 10 years. Everyone in the city is shocked. The Lower East Side is in tatters. Is that the longest sentence ever in this point? Like, I feel like you get six weeks for stabbing people to death in this era.

Yeah, I mean, for him it sounds very, very long. It does sound like they really had no, no, like, it sounds like European sentences right now, you know, Like how it works in Sweden. When it comes time for him to get sent up on a train to Sing Sing Prison in upstate New York, Austin, where Don Draper lives. There's a giant crowd waiting for him at Grand Central

and a ton of reporters to send off the city's number one public enemy. When he gets to Sing Sing, he is not in for a good time. Whatever you've seen about the American prison system right now, back then, it is insanely worse. And Sing Sing, at that time, is the most notorious prison in America, known for its brutality and corruption. Prisoners are leaving, like, permanently crippled

just from noun nutrition and diseases. They straight up torture inmates all the time. There's no oversight, no lawyers, no one looking out for prisoner rights. And back in the city, with Monk-Gon, the Eastman gang, it's just too big and too wild, it can't be managed. Too many factions, too many people, too much violence.

Two aspiring young leaders, Otto Bennett and Morris Rothschild, they fight a brawl for control, but neither one establish his dominance. Another young leader named Kid Twist, not the one of murdering fame who came 30 years later. He has six members of a rival faction kill within a week.

It's also kind of weird. These guys are gangsters with tons of rackets. But one of the things mentioned that Kid Twist does is he forces every small food store to buy a celery tonic from him at an inflated price.

I mean, I don't... Like, the Dr. Browns kind of hits, but I just don't know as like a criminal hustle. Like we often mention how the best crime moneymakers are simple things, but this seems like a little quaint.

Yeah, yeah. Yeah, yeah. Quit, Twist is in control for four years until 1908 when he's gunned down by a five-pointer. Tammany Hall tries to spring Monk every so often because they need him to get out the vote, but he ends up serving five years until a new law is passed that says, first-time offenders could be eligible for parole after half their sentence is served. Wouldn't you know it, Monk passes the parole board, review his first time up in June of 1909 he's released.

He's forced to stay in Albany for a year, which is a crime that no one should actually suffer. I kind of like Albany, but you know, not a good place to get stuck. But he returns to New York in 1910. But my friends, as they say, you can never enter the same river twice. I must be getting old because that's the second time I've heard that phrase in a day. Is that confused? Who said that? That's definitely not confiers.

Who said that? Is it the Buddha? I don't know. One of those guys, yeah. I don't know. I feel like it's someone more modern, but let us know in the comments. Let's get some algorithm action going. because of that, because I don't know things.

New York is a chain city, right? His neighborhoods have been taken over by hipsters, opening up barbershops that cost $47 and vegan cafes. I'm just kidding. That doesn't happen until like 100 years later. But the city is different, right? His gang is broken up.

Many of his partners are gone. The police are actually much more firm control. There have been a sort of reform within the department. Politicians have to be less overtly corrupt. Some of the slums are being cleaned up a little bit. The police thing is interesting because it really seems from reading, Like they get things somewhat of a handle on things, right?

Only to have it blown wide open and worse than ever in a decade or so because of prohibition. Monk's also 37, which is ancient for a gangster in those days, though it is prime age to get a side hustle as a podcaster going. His body is breaking down after so much violence and five years in Sing Sing. He's weakened, rumored to have an opium problem. There's also a lot more Sicilians coming to the neighborhood who have their own gangs and don't know of Monk. You know, I'm thinking now, for some reason, of a primetime sitcom. It's called You Don't Know Monk. And it's like a washed-up gangster at home with these illegitimate kids were saying.

It sounds great. You know, there was a reality show. You know, I think we talked about it in our episode on, like, the Israeli organized crime where they, it was like a show where you live with someone opposite from you. It's like a vegan, like a meat eater, like a family of like butcher's, I don't know, something like that. Like what's sort of thing? But there is one where they have a model live with a family of like of gangster. basically. Like a gang,

well, the husband's the gangstered like you run sanitation stuff. I think there's all, well, I guess now there's so many podcast former mafia guys that were,

I just know, we had, what am I talking about? We had growing up Gotti, dude. Oh, right. Yeah.

I was like 15 years ago. Yeah, yeah, yeah, so yeah, there, I guess there's a ton there's a lot of that.

I don't know if it's as fun as you don't know monk is in your head, but those shows exist, you know? Um, and mob boys. My boys was a big thing too,

right? Yeah, yeah, Okay, all right. Yeah, I'm just going to watch him. That's what I'm saying. Yeah. I don't think you need to watch him.

So he's sort of an outcast, not getting the respect that he had earned. The police harass him. They beat him. Others inform on him. He's basically a marked man. He can't get anything going. He's doing small-time stuff, moving a little opium. There's actually an opium gang wars where it's being waged, and he gets caught up in it,

charging convicted with manufacturing opium, and he has to do eight months of jail time again. When he gets out, the police tell him he's got to leave New York or they'll be on him every day. He moves back to Albany. He gets busted then again, I think arrested upstate for burglary. He gets off. He gets arrested again in New York in 1915. He ends up getting sentenced to three years in jail, but gets released in September of 1917 after having been two-thirds of his sentence. It's now September, 1917, six months after America enters World War I to save Sean's ancestors.

He said, Eastman is 43 years old, and he decides his purpose and path to redemption is signing up to go fight in the war. He shows up to the Brooklyn Armory and the sergeant examining him, noticing how beat up his face and how many scars he has on his body, asks him what battles he's fought in and he replies, a lot of little wars around New York.

He's got that Purple Heart for War even though he's never left the city. He joins the New York National Guard as an infantry man, and his 20 years younger cohorts, they nickname him pops, right? He goes through training, and in May of 1918,

he shipped out to France. He's kind of doing the reverse Tommy Shelby thing, right? He's using the skills he picked up on the streets to fight in the trenches in World War I. I think there's actually Christopher DeStefano a bit about this,

like his grandfather in World War II with like a switchblade wearing a tank top. It's very funny. Find it if you can. But it's not just Zij Germans and France the boys need to watch out for. To quote from the book, Heroic gangster,

the troops of the 27th division bivouacked for miles around the Somme estuary. But on General Pershing's orders, they were kept as far away from towns as possible to minimize the VD rate, which if only someone have been around to give that advice to a young Sean Williams

in terms of avoiding Berlin back in his 20s. Don't bring me into some French anecdote, right? This is on them. I'm not getting involved in that, man. Lost a lot of good men that way. Monk is with that 27th division, and they march right into the insane front lines. This is that kind of grueling trench warfare, heavy artillery, shell shock type stuff.

Go watch 1917. That movie absolutely rules. Monk impresses all his fellow soldiers, right? He's cool and collected under fire, fearless, always volunteers for the worst to the worst, saves his soldiers' lives, and is deadly with everything from bombs to his bare hands. He sees a lot of action, right? Artillery shells raining down like Niagara Falls. He gets a reputation for bravery. He says stuff later on, like, quote,

there are a lot of dance halls in the Bowery tougher than that so-called Great War of theirs. A lot of his fellow entrymen in his division are killed and wounded. Montho, he stays on the front even when his fellow soldiers are allowed to step back. Some man just love the thrill, Sean. I got to tell you. Sounds a lot like a lot of photographers that I used to work with. Yeah, me too.

Some of them just want to run a bullets, man. They're insane. They want to wear scarves in weather that they don't need scarves in and they want to run towards bullets. Each one, to a tee. He's running straight into machine gun nests as people around him lose their minds,

crawling through mud and lobbing grenades, following it up with like bayonet stabbings. He takes a couple wounds. He even gets chlorine gas at one point. He even leads his fellow soldiers into battle as shock troops at the Hindenburg line, which is apparently one of the most, if not the most formidable German defense areas. In March of 1919, Monk finally returns home with his fellow soldiers after the war is won,

eventually parading through Brooklyn to cheering crowds, and then an even bigger parade of Manhattan through Fifth Avenue. Monk has a contingency of street types cheering for him at this point, and only then did some of his army buddies realize that he was the Monk Eastman. He's formally discharged in April, and all his army superiors and politicians petitioned the governor to get Monk's rights that he lost for his felony convictions, reinstated because he's a war hero, and it actually works. Quote, Monk Eastman wins New Soul,

reads the headline of one of the local papers. One-time bad man of the east side, survivor of 100 gunfights, political world ward healer, repeater at the polls, and finally convict because of his exceptional record in the army overseas.

Even the New York Times reports on it. That's how big a deal it is. Yeah, I mean, the guy, he was a bulletproof, like, murderer. They should have just stuck all of these guys on the front lines, the war would be over in days. I mean, some of them, some of them did. Now, there's speculation

about what Monk gets up to after this, a lot of it, because of what happens next. Some say he was living on the straight and narrow, others that he was back as like a small-time gangster, others that he was in the opium dent. Seems most likely he was sort of living legit, I think. Whatever the case, Christmas Eve, 1920, he ends up at an all-night restaurant

with some former gang members, drunk, singing with a few groups joining together. According to some, there's an argument in altercation, and everyone splits up. Monk staggers out at 4 a.m., heading to the subway station. Somebody rolls up on him and shoots him five times, and his body, after so many other wounds, finally gives in. This is a movie now, right? I mean, this must be in a movie.

I can't believe that this is only in books. This is so perfectly wrapped up. Yeah, yeah. I mean, it's kind of got that, what's that thing where, like, every man just wants to die bleeding out in the snow, you know? but that except in the snow. It doesn't say it's Christmas Eve, whatever. We're going to assume it was snowing, right?

And he's bleeding out because the trains were over at, well, in that area they were overhead back then and just bleeding out on the ground after he returns a war hero and he got his life together. I mean, it's, yeah. There you go. Perfect, poetic. You've written it.

Yeah. There's a massive funeral procession on the Lower East Side, full of gang members and soldiers, six stretch limos, 20 horse-drawn carriages, thousands lining the streets, his army buddies giving him the honor guard, one gives a speech about how Monk

saved his life during the war, and at first, no one has any idea who killed Monk, but a whole lot of theories fly around until a week later, when a Prohibition agent turns itself in and claims he acted in self-defense. Most seem to think this is nonsense the agent had actually been a gangster before.

He pleads guilty to manslaughter and gets sentenced to three to ten years, but is paroled after only 17 months, and this, to friends of Monk, looks pretty suspicious. Monk's death, it symbolizes the death of an error, right? And it's no coincidence. It happens right at the start of Prohibition.

The Lower East Side of Manhattan Criminal Elements, they transitioned from like this wild west gang, shoot him up brothers into something more organized thanks to him. But it's nothing like what is going to come over the next decade with Prohibition. The organization, the sophistication, the money and the murders. The businessman gangster. No more cauliflower ears and dirt dive bars. Monk Eastman, he represents his crucial moment in the evolution of organized crime in America.

The gangs that have come before him, like I said, they're like these street fighting clubs that do crime on the side. The ones that come after him, that's lucky Luciano, Arnold Rothstein, Lanski. They build these criminal monopolies that take over entire systems, entire industries across city and state lines.

So, yeah, that's the life of war hero, gangster leader, Monk Eastman. Patreon.com, such as an oral podcast, support us. If this is your first episode, listen to others. Enjoy yourself. let us know what you think of Sean's living room.

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