The Kevlar Gangster: Jack 'Legs' Diamond and Murder Incorporated

Organized Crime and Punishment

Title: The Kevlar Gangster: Jack 'Legs' Diamond and Murder Incorporated

Original Publication Date: 7/5/2023

Transcript URL: https://share.descript.com/view/v9MXHPNM2rW

Description: In this episode Steve and Mustache Chris delve into the captivating life of Jack "Legs" Diamond, one of the most notorious gangsters of the Prohibition era. From his humble beginnings to his rise to power, we explore Diamond's journey through the criminal underworld. Known for his involvement in bootlegging, gambling, and other illicit activities, Diamond quickly gained notoriety and influential connections. However, his rise to power was marred by violent gangland conflicts with rivals such as Dutch Schultz. Ultimately, we unravel the decline of Diamond's criminal activities and the mysteries surrounding his unsolved murder in 1931. Join us as we delve into the enigmatic life of Jack "Legs" Diamond and reflect on his enduring legacy as a symbol of the Prohibition era and the fascination with gangsters in American popular culture. #TrueCrimeStories #OrganizedCrime #MurderInc #Mobsters #CriminalUnderworld #Assassins #CrimeSyndicate #Hitmen #InfamousKillings #GanglandHistory #CrimeFamily #MafiaChronicles #ContractKillers #Crime

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Begin Transcript:

[00:00:00] Welcome to Organized Crime and Punishment, the best spot in town to hang out and talk about history and crime. With your hosts, Steve and Mustache, Chris.

We are very deep into the contract killing startup enterprise of the Mafia Murder, Inc. We have seen that Murder Inc. Wasn't just a add-on or a side project of the American Mafia and organized crime. It was central to the formation of the mafia itself. And we're building that story as we go along. We've met a lot of really quote unquote, interesting characters so far in the development of Murder Incorporated.[00:01:00]

Today we're going to take some time to zoom into the life of one of the more fascinating stories and characters. Jack Legs, diamond Mustache. Chris, why should we take a closer look at Jack Diamond? Yeah. Researching the, like our deep dive into Murder Inc. I came across Jack Li's Diamond and um, The, uh, labor Sluggers Warrior was, uh, little Augie's bodyguard, or on and off bodyguard.

And it was, honestly, it was his nickname that kind of caught my attention. Jack Legs Diamond, it's just such an odd nickname for him upstairs. So I just kind of went down a little rabbit hole and. Soon as I kind of got into his story, I'm like, this guy is, this guy is an insane story. Like, how about, how am I, no, sorry.

How haven't I heard about him? Like, he's like trips around the world, you know? He was like dating the equivalent of movie stars at the time and like, He had multiple attempts on his life and he was able to survive most of [00:02:00] 'em, you know, uh, and just researching it, like kind of, Jack doesn't even really kind of, he doesn't even come across as like a real person in a lot of ways.

He almost seems like a, kind of like a evil cartoon character, if that makes sense. Like you'll, I think you guys will agree once we start getting into his life story. Yeah, I really ag I agree with that, that there's so many people and sometimes somebody like Jack's legs diamond, he just rises to the top.

Let's start off with it right in the beginning. Can you tell us, uh, a little bit about his background and early life? Jack Diamond was born on, uh, July 10th, 19, uh, sorry, 1897 to Sarah and John, uh, Moran. Sarah and John. Sarah and John would leave, uh, Ireland for Pennsylvania in, uh, uh, 1891 and a few years later, his brother, uh, Eddie was born.

And like many, uh, Irish immigrants coming, uh, To America, the easy wasn't going for them at all. Right? It [00:03:00] not just the Irish, it was the, you know, Jewish immigrants and Italian immigrants that were coming over at the time. And to also add on top of it, Sarah suffered from, uh, debilitating arthritis and other health problems.

And then by 19, uh, 13 and affection in her lungs, uh, Would actually kill her. And it was very common in those days cuz people just didn't understand, uh, just how bad, uh, living in the unsanitary conditions that, uh, they lived in. We touched on it a little bit in the, uh, murder Inc. Uh, I believe was Murder Inc.

Part one, where we talked about the living conditions in Brownsville, which was particularly worse, but in much of the United States and the, especially the major cities, they, some were a little bit better, but most of 'em were, were really bad. Um, Yeah. And as soon as, uh, Sarah died, uh, John moved his whole family to, uh, Brooklyn.

And, uh, this is kind of where Jack Legg's diamond, uh, criminal career, [00:04:00] uh, kicks off. Yeah. So I mean, I, I think we've seen this time and time again that. Some of these guys had really rough childhoods and Jack is certainly no exception. I think in time, in those times in general, we would say that almost the perfect childhood back then would be considered a rough outcome upbringing today.

But, um, how did Jack fall into crime? Yeah, basically soon, almost as soon as he got to New York, he. Started getting into involved in criminal activities. He got involved with a, a famous Irish, uh, gang called the Hudson Dusters, which is a, i, some of these old like gang names are really cool. Like we did like the five families and they, they, I don't know, like the Gambino family and stuff, like that's a cool name, but some of these old Irish gang names or.

Wow. Like they just, I don't know, know. A lot of them are just fond names. There was another gang we talked on, I think it was like Murder Inc. Part [00:05:00] three was the Ocean Hills Hooligans, which is, I don't know, some of these old timey gang names are fun. Uh, but the Hudson and Dusters, uh, yeah, they, they were no joke man.

They had connections to Tammany Hall and like, and writing organized crime and like huge sections of New York. Um, eventually I think, we'll, We'll do like a whole thing on the Irish, it's wasn't the Irish Mafia, but people call it that. But Irish organized crime in New York and around the United States, cuz it is such a big subject.

Um, yeah. Jack would find himself, uh, in jail for the first time in, uh, 1914. He was arrested for, uh, robbing a jewelry store. Um, but, uh, during, I guess he. Spent a couple years there cuz like during World War I, Jack found himself, uh, swept up in the patriotic, uh, fervor of, uh, of, uh, Of the times and he would join the army.

But uh, I guess those feelings didn't last very long. [00:06:00] Cause he would be charged with the desertion in 1918 and would be sent to Leavenworth for five years, but only ended up serving, uh, two years of the sentence. I think that those criminal gangs, back then, it was really almost something. In between a social club, a sports team, like they were, they were almost like the, the minor leagues for criminals.

Like you would have gangs that weren't necessarily all, you know, maybe they were into some light criminality. You might call it vandalism or something like that. But I think that the, the more powerful gangs and the real criminal organizations would kind of pick out what, uh, prospects from those gangs.

Oh yeah, for sure. You know, and it's like even at this time it was like things are kind of getting more organized, but there it's still really not far removed. I guess the, I guess the most famous one we would be like Gangs, New York, where you had like a bunch of these kind of [00:07:00] small gangs and that there would be like the one powerful gang that kind of ran things, but they, it was like kind of very loosey goosey.

So like we're still kind of in that, in between stage where things are. They're getting more organized and, uh, more top heavy, but we're not quite there yet. Or even, I mean, it's kind of a sillier example, but West Side Story, the Sharks and the Jets, it's the kids living in the neighborhood that they're maybe the same, you know, the Puerto Ricans and the Iris or in, you know, in our context, the Italians and the Jews and the Irish and the kids from the.

A couple of blocks just to start to group together for maybe certain elements of self-protection, a little bit of identity, and there you go. And then some of the gangs that maybe are, like you said, are a little bit more organized, then they might get into shaking down or stealing or, uh, roughing up people.

And that's how those things kind of evolve. [00:08:00] And how did legs evolve his criminal career? Yeah, when he got out, uh, he got out, uh, Jack would be released in 1921 and upon his release he would be hired by, uh, I guess Arnold Rothstein, uh, noticed him and he would be hired by, you know, Arnold Rothstein to be his, um, bodyguard.

You know, I, I don't know if people are familiar with Arnold Rothstein, but Arnold Rothstein, we're gonna do, I guess we're gonna have to do a big series on him just cause from even me and you researching it, we didn't realize. Just how important Arnold Rothstein was to organize crime, um, until we started really seriously researching this subject.

Uh, he in a lot of ways basically created what we would consider organized crime in New York. Um, in a lot of ways, um, I guess he would be most famous for, he, he. I dunno. People claim that he's the one that rigged the 19, uh, the 1919, uh, world [00:09:00] Series, the famous Black Sox scandal. I mean, I would say that he did do it.

We can't say a hundred percent for sure, but I would say that yeah, Arnold Rothstein did rig it. Um, Jack would also work as a, he would also work as a hired muscle once in a while for a famous, uh, labor slugger named, uh, little Augie Jacob Origin, um, uh, who would, uh, end up getting killed by, you know, people that were familiar with Leke and, uh, Lei be Holter and Jacob Shapiro.

And this is one of the times that, uh, Jack almost loses his life, where we're gonna get into that in a little bit. Um, Yeah. And, and, uh, people probably wonder, look, how did Jack get his nickname? I mean, the one theory is that he got his nickname from Legs cuz he was able to run away from uh, these hit, uh, these hits that people would try to pull on him.

Uh, and another theory is that he was a good dancer. Which is, I always, that [00:10:00] is a funny image to me as this, you know, this gangster that gets his nickname legs cuz he is a good dancer. It's just not something you associate with organized crime. But, but that's one of the theories. Uh, I don't know, maybe he had really long legs.

I don't know. Uh, we only got like a couple photos of these guys, right? Uh, I mean, you can look up a picture of Jack and, um, You can, you know, there's, there's photos of 'em, right? But there's not many. Um, Jack was also known, like during this time for living like a flamboyant lifestyle that like included heavy womanizing.

I guess his most famous girlfriend was a dancer named, uh, Marion Roberts. Uh, Once he started dating her, he would, he showed her to, uh, you know, famous, uh, dance, uh, teachers in and around New York, cuz you know, Jack had the connections. He was, uh, tied up with Arnold Rothstein. Um, so we can kind of see here pretty early on that Jack kind of becomes like a, what [00:11:00] you would call celebrity gangster, which was a new kind of phenomenon at the time where you saw it with Al Capone and, and.

A couple other mobsters. But, uh, yeah, Jack was kind of, he was a full-blown celebrity in a lot of ways. He was like dating, like the equivalent of movie stars at the time. Like these, uh, these dancers, these singers were, I would be kind of like, as, I wouldn't say it was as crazy as like, say he was dating Scarlett Johansson, but you know, something like that.

Were. These were well known individuals at for the time, uh, and he was also a gangster that was killing people, as bizarre as that sounds, Steve, here we are a member of the Parthenon Podcast Network, featuring great shows like James Earley's, key Battles of American History Podcast, and many other great shows.

Go over to parthenon podcast.com to learn more. And here is a quick word [00:12:00] from our sponsors.

As somebody who I, I think I'm as knowledgeable about the mafia as the next person and really interested in it, and I never really realized how deeply Arnold Rothstein was in the formation of what we know as the mafia. Like you said, I didn't think most people, if you know his name, you'll just associate it as the low level.

Crook who worked on setting up the 1919 Black Sox, uh, world Series throwing scandal. But this guy was absolutely at the nexus of everything in the New York organized crime. During prohibition in that time period and he wasn't, bootlegging wasn't even like his main thing either. He was involved in a lot of other things, and it's just the fact that he died kind of early that [00:13:00] I think if he had lived a little bit longer, we could have seen a very different mafia come out.

Yeah. And also he was also influential in bringing like the drug trafficking and organizes the drug trafficking come to the states. You know, even for people who probably know a little bit about Arnold Rossi, and that's probably a little shocking to 'em, but it's, that's the truth. You know, I learned that reading, uh, Rob Cohen's book, uh, tough Jews, and he talks about how in the Jewish community, they just don't even talk about it like that Arnold Rothstein was responsible for drug smuggling.

It's just something that's. You just don't talk about it. That's a big part of that book is just how the Jewish community, uh, has dealt with the fact that, you know, very early in their history, they were heavily involved in organized crime. Um, it's a, it's a very interesting book act like, uh, just in terms of, there's a lot of like psychoanalysts, uh, analyzing in it, uh, um, just how a community was able to deal with, uh, [00:14:00] with that fact and, um, Just, it's well read.

It's interesting history about the time period that we're talking about right now. No, we haven't in this whole series talked much about prohibition and that'll be a whole different, uh, series, but a lot of these guys made a lot of money in prohibition. What was legs involvement in prohibition? So, yeah, prohibition obviously was a made selling liquor illegal.

Um, you could still sell it. I don't know. It's a long story. We're not gonna get into it. But, uh, Jack came up with a brilliant idea During prohibition, he would steal the alcohol from the people illegal selling it so, During prohibition, it was a common practice to dump the alcohol that was like in barrels, like right before you hit the New York Harbor, and then you would go collect it later in the dead of nights and just so you weren't obvious about it.

Right. And Jack would pay like local kids, like a nickel for every [00:15:00] barrel that they were able to collect from these barrels that were being left in. Overnight. And then he would, uh, he would obviously sell the liquor at his own clubs, right? So Jack would open up the, the hot seat TZ Club that oversaw like most of the alcohol sales in the Manhattan region of, uh, New York.

Uh, this club would bring Jack into conflict with other bootleggers. Obviously this is kind of where, like the bootlegger war starts is cuz there was just so much money to be made. So everyone was doing it all at once. And this inevitably, You know, brought conflict. This is where people argued that prohibition was an absolute failure in a lot of ways, cuz it, it brought like a crazy amount of gang violence where like all these different gangs and all these different bootleggers were fighting each other.

Uh, yeah. They would bring, uh, our, our buddy Jack Lake's diamond into conflict with Dutch Schultz who is uh, we're gonna end up doing an episode on him cuz he's just a really important [00:16:00] uh, gangster. In general, but around this time period. But Dutch was also, um, insane. So, and, uh, So, yeah, in 19, uh, sorry. In July, uh, 1929, Jack and like a fellow gangster, Charles would, uh, they, they shot up, they shot like three drunken brawlers that were in their club, and, uh, two of them, uh, uh, two of them would die and one would, uh, one would survive, but barely, and to cover up any potential witnesses to the very public crime.

Cause they did this while. Everyone's around. Uh, two waiters. One, one hat check guy, one bartender would end up going missing. They ended up finding one of the, one of the, uh, I believe it was the waitresses. Uh, she was shot dead, uh, in New Jersey. Uh, Jack obviously wasn't charged with any of the any.

Anything for this, right? Because there was no independent collaborating evidence, but the city did force him [00:17:00] to, uh, close down his, uh, speakeasy, which is, why was it open in the first place? If they knew it was there, it should have been closed down, right? That's just the whole insanity of prohibition, and I guess we'll get into it, but it in a future series, is that it created criminality that wasn't there in the first place, and it, it created a, a, a situation where, You had tole illegally import the, the booze or illegally make it.

And so they're, you're creating an unsafe situation there. And then you're creating a situation where the mafia goes and steals somebody's booze. They have no recourse. You can't go to the government, you can't go to the police, you can't go to the courts. So then you have to go to these organizations like.

La Ostra that are just starting to like an infection, like just work their way into every system. And I think that [00:18:00] that's a, one of the things, I don't think that the, um, like I said, again, this'll be something that we get into a lot more and I'd love to hear what people, their ideas. I don't think that the prohibition made the mafia, but I think it was almost like steroids for the mafia.

Yeah, I would generally agree with that. I mean, I mean, me and you have gone back and forth about prohibition. I think there were, I think there were some people that just saw what liquor did to families and did to people, and generally thought like, this is crazy. Like why are we allowing this to go on?

Like, it just destroy people's lives. And I think there were people that were genuinely. Concerned about the welfare of their neighborhoods. At the same time, if the city's going like, oh, you're gonna have to close down your speakeasy. I'm like, why was it opened up in the first place? Like if you can't enforce the law, or I.

The law's unenforceable or not willing to go to certain lengths to actually enforce the law. Like I don't, what are you doing really? [00:19:00] Um, just, that's my opinion, right? I mean, when we get into prohibition, I, I have some interesting takes on the whole thing. Probably that's not, um, I guess popular opinion, but, you know, we'll save that for another episode because like we said, it's, it's, it's a huge thing in a lot of ways.

It created the mafia. Some people say it, it created the mafia. I, I don't know if I'd go that far, but it, it definitely helped. Uh, yeah. So after his club gets closed down, you, you think Jack would, you know, lay low for a bit, you know, like have some of the heat, uh, come off? No, he goes immediately starts kidnapping truck drivers and kidnapping a lot of people.

And one of these truck drivers that he kidnapped was Grover Parks. Um, and they. Basically beat the crap out of him, you know, and tortured him because they, I dunno, they thought he had, the hard sider was on his truck and he denied it and, I couldn't never actually find out if there was [00:20:00] actually cider on the truck or not.

Uh, but they ended up just letting him go and then he, Jack would end up getting charged for this. And there was a couple other kidnappings that he'd done. I just thought that was crazy. Like you beat a guy within an inch of his life and then you just let him go. Like, of course he's gonna go to the cops.

The cops already have like, you know, uh, you know, like meat, uh, sorry, a heat seeking missile on you considering what you. Basically got away with three murder, uh, with two murders that they know of. I just thought that was so crazy. You think he would lay low? No, not Jack. He just starts kidnapping people and beating them up.

He even after prohibition goes away, Jack doesn't calm down or go straight, if anything, I think he really ramps it up. But can, and in his next adventure, he goes on a grand tour of Nazi controlled Europe. Yeah. This has gotta be one of the crazier stories in, in Bob History that I've seen just cause it's.

Not crazy in the [00:21:00] sense that he is gr it's just, it really is really ludicrous. Um, yeah. So I guess in one of the more bizarre stories about organized crime around this time period, Jack would go on a trip to Europe and I guess he, I guess they logic behind it. Maybe he was making some connections in Europe or he was just trying to get.

Some of the heat off of him, because I guess he was like radioactive at this point. Uh, so Jack would, bo would board, uh, the ocean liner GaN land. And the, the, the police initially thought that Jack was trying to leave New York. Uh, so they checked two other ships and they just happened to be the wrong ones.

So he got on this one and apparently while he was on, uh, This Ocean liner, he basically spent his entire time, you know, smoking cigars, smoking cigarettes, drinking, playing poker, and apparently made thousands of dollars. It was on this ship, there's like conflicting evidence where apparently the captain of the ship said, oh, he didn't make that much money, but I don't know, who knows?

Let's just say he made [00:22:00] thousands of dollars, cuz it's more interesting. Uh, yeah, the n no N Y P D telegraphed, pretty much all of Europe saying like, if you see Jack detain him immediately, this guy's a ruthless criminal murderer. We want him back here. Um, and once Jack landed in England, he was informed that he was not going to be allowed to enter the country.

And England's like, oh, I don't know, like, what are we gonna do with this guy? And then I, he said he wanted to go to Vichy France. I guess Vichy France is famous for, Springwater. Jack was clearly lying about why he wanted to go there. Um, So Angland ended up just sending him to Belgium and he ended up landing in a Antwerp where he was immediately detained.

And then once he was detained, he in, uh, Belgium. Yeah. So he was sent to Akin Germany where he was, um, he was immediately arrested there too. And, Let's just pause there for a minute. Like, does this not sound like something out of a cart too? Like this guy [00:23:00] sneaks outta the United States, he goes to England, England's like, oh, whatever.

You're going to Belgium. You claim you wanna go to France. We're gonna, you can go to Belgium. And then Belgium's like, well, you're not staying here and we're gonna send you to Germany. And, and then they're like, he goes to Germany and. Basically, Germany says like, okay, you know what? We're just gonna deport you back to the states, like we don't want you here.

And he would think like, oh, this crazy story ends. No, it goes further. So he goes to the states, he ends up landing, he ends up going to Philadelphia, where he is immediately arrested. And the judge. Goes to him. He's like, okay, we know what, here's the deal. We'll drop all the charges. You just gotta get outta here in an hour.

And Jack's, okay, fine, I'll get outta here in an hour. And he left and went back to New York like, like what a bizarre story. Like how many countries did he go through? Uh, I don't even know how, I don't even understand how he thought he would get away with it, but I've never heard anything like this. And all the [00:24:00] mob guys that we've read about have you.

Well, there's a little hints in it, like with, uh, Vito Genovese going to Italy, but he had a place to go in Italy. I don't understand what legs was remotely trying to do, going to Nazi Germany. And the Nazis don't even want him. It kind of sounds like one of those, uh, adventure books from like the thirties and the forties where, uh, The person, like, it's almost like he's an undercover agent or something, but he's not, he is just a, you know, a pretty low level criminal.

It, it's insane. Yeah. It's basically, it's just like going from one country to the next and each country just going like home, man. Like, we just don't wanna deal with this. We'll just pass along to the next guy, you know? Like, uh, that's a Monday problem or something, you know, it's the equivalent of that.

We're going to leave Jack in Philadelphia for a minute to just talk about how many times this guy was [00:25:00] almost murdered and lived through it, like they call John Gotti, the Teflon Don. I think that Jack Diamond was made outta Kevlar. Yeah, we'll go through like the couple of times that, uh, well, a couple more than a couple of times that Jack was almost killed and just, uh, the, some of 'em are really crazy where, so the, from what I was able to research, the first attempt on Jack's life that, uh, I'm aware of, uh, There must have been like a couple other times before I just wasn't able to find it.

Uh, it just kind of goes with the lifestyle being organized. Uh, criminal at this time period was in 1924. He was trying to rob a, a rival gang's liquor truck and was hit. By shotgun pellets and Jack would obviously survive. Uh, this, so no, from the least from what I read, no serious injuries, but that, you know, imagine that's the first attempt on your life.

You're being shot by like a shotgun. It's not, [00:26:00] uh, It really is nuts, you know? And then the second time came in 1927. And we kind of touched on this a little bit before when we covered the Labor Slugger words. If you guys go back and maybe listen to that episode, uh, that's gonna be, that was Murder Inc.

Part two. Uh, Jack's, Jack's brother was, uh, he was the guy that was little Augie's bodyguard for most of the time, but he, I guess he had the day off that day. And so Jack was covering from, in October 16th, uh, 1927, little Augie was shot dead by three men and Jack was hit. Uh, Twice, just like right below the heart apparently.

And Jack was taken to the hospital. He was interrogated by police, but Jack refused to talk. And at one plea, at one point the police suspected that maybe he was in on the head. As crazy as that sounds, even though he was shot near the heart wasn't like he was shot in the arm or something. He would, you know, if he was shot in the arm or like non-life threatening.

I [00:27:00] can maybe understand where the police were coming from, but not when you were shot, like, you know, uh, execution style in the chest. Um, but those suspicions were dropped, obviously. Um, yeah. Shot twice right below the heart, um, covering for your brother who was supposed to be working that day. Like that's, that's, that's wild, eh?

Um, this is probably the crazier one. Like the third attempt was, uh, was on October 12th, 1930. Um, so. And you would think at this point that apparently Jack would just not leave his house in October, but just considering it seems three times and, uh, he must have just looked at the calendar and thought like, oh, October.

Like, yeah, probably someone's gonna try to kill me, kill me this month. And uh, so yeah, Jack was at his hotel room, uh, and it would be broken into and he would be shot. Five times. Yes. You heard that like right. Five [00:28:00] times. Uh, while he was still in his PJs and Jack was somehow able to walk out of his room and when the police found him there, they just couldn't understand.

Like, how did you, I. How did you get out of the room? And apparently Jack responded by saying like, I took two shots of whiskey. It gave me, gave me enough strength to, I just get this image of like the guy in the cartoon and that like drank something after he is been shot a couple times and it's just like kind of spilling out of him.

That's the image I got cuz he is like in his PJs and he's been shot five times. Um, Jack would end up, obviously end up going to the hospital. He would recover and he would get out on December 30th, 1930. So I guess he didn't make it home for Christmas, but you think about it like he got shot twice right below the heart, got shot with a shotgun, and then this case, uh, five times or up to.

I dunno, eight or nine times that he's been shot. Nobody's been able to kill him. So Jack finally ran outta [00:29:00] lives and he can't respond anymore. How does Jack ultimately get taken down? We all know, like some people are kind of born lucky. Everyone knows the type of person that just, things kind of go their way.

But like eventually even for those people, like luck does run out. Uh, Jack was staying at a rooming home while he was on trial for kidnapping. Uh, that he would be acquitted of on, uh, December seven, uh, 17th, uh, 1931, and he was the, he went out with the friends and his mistress. They went out for dinner and the night of drinking to celebrate, you know, obviously him escaping the law once again, and the late hours of the evening.

And Jack being hammered. He stumbled back to his rooming home where he passed out on his bed, and approximately an hour later, this is from what I was able to research. Uh, men broke into his apartment and one held jack down while the other person shot Jack. Uh, Point blank in [00:30:00] the back of the head three times.

Pretty brutal. Like, like really ruthless execution, right? Concerning. He was like right in the face. Uh, or at least his face would've been blown out. But I mean, I. Given the amount of times that he was able to get away, I guess to a degree I can understand the, the overkill. Yeah. It's really, really crazy, crazy story.

You know, uh, the, I don't know, it's obviously not the same rooming home, but like, uh, there's a picture of where. The rooming home was, and you can kind of see where exactly where he was killed and even, but even with, uh, Jack's death, like the story doesn't end there. Like it gets even crazier. I didn't even know anything about this until I started researching, uh, the subject.

But like there's many different theories about, um, like who actually killed, uh, Jack Diamond and like some people say it was Dutch Schultz, which. It is believable. Dutch killed a lot of people, especially [00:31:00] like fellow bootleggers. Um, some say like it was like relatives of like, uh, another Irish gang that Jack kind of screwed over.

But I found like the most interesting theory was it was the Albany Police Force themselves. Uh, Apparently Jack had been trying to move into Albany, uh, once his club got closed down and he was having like a lot of problems in, uh, his more traditional areas in New York. So he saw an opportunity here. But a, a gentleman named by Dan O'Connell, who apparently ran like the Democratic, uh, political machine at the time.

He made a big point that there was gonna be no organized crime in Albany, at least, you know, stuff that he. The stuff that he was doing was fine, but there wasn't gonna be, uh, any other organized crime, um, anybody knows about, like these political machines, Republican or Democrat in New York. It was particularly bad with the Democratic party, uh, a lot of the way.

It was, uh, [00:32:00] kind of hard to tell the difference between them and organized crime and apparently Dan O'Connell. That's what I read. Apparently put a hit out, uh, for, uh, on Jack Diamond and a gentleman by, uh, William Fitzpatrick, who was sergeant at the sergeant at the time. This is how the theory goes, where the guy, him and his partner went in there and they killed Jack.

And because shortly after he ended up becoming the chief of police, and the theory goes, this is kind of his reward for getting rid of Jack Diamond. You know, and then 20 years later, William would be shot by one of his own detectives in his own office. I, I tried researching this cause that's wild, right?

Like, like a detective shoots the chief of police in his own office. You think that you would know more about that? But I, I, I tried finding exactly what happened and I was having a difficult time doing it. Like, I'm gonna keep on digging and once I do, maybe [00:33:00] we'll do like a short about it or, You know, we'll explore it if I could act cuz it is.

That is. Insane that a police detective shot the chief of police in his own office. I guess maybe the theory, my theory is maybe John saw all the type of corruption that was William was involved in and like didn't want any, like took something snapped because he ended up getting acquitted of the crime.

Later on. So that's my theory is he saw the type of corruption and like the type of corruption was coming out. And I, it, it, that's a really bizarre story. Like to me, it, this whole police killed Jack Diamond seemed really believable in my opinion. And it's, there's a lot, there's a couple other people that really, truly believe this is what happened.

Um, Maybe they didn't have anything to do with it. So maybe it was just Dutch salts. Maybe it was, uh, some other Irish [00:34:00] gangs. But this police theory, I think, has a lot of legs to it, not to be, uh, Cheesy. But, uh, there, there's a, there seems to be a fair amount of evidence that this, these are the people that, that killed eventually killed Jack.

Steve, here again with a quick word from our sponsors. I think you can see how I, I mean, I agree with you that that could carry some legs that, again, uh, excuse the, the pun, but how the, the organized crime kind of bleeds and what crime in general bleeds into the political machine, which bleeds into the police department and they all just kind of blend in together.

And so you can see how these corrupt. Political machines are operating with corrupt police departments and you have the criminal element that's just [00:35:00] ripe for anything to basically happen. Yeah. And then, uh, Jack's widow Alice would end up getting killed in her Brooklyn apartment. She was only 33 years old.

And I don't know, maybe, maybe it was the mob that killed her, cuz they. They were worried that she was gonna start ratting or who knows, maybe it was the police department and she got wind of what happened and we couldn't have her talking about, you know, it was the police that actually killed my husband.

Um, maybe that's what happened, you know, either way just shows you kind of how ruthless it was at the time. Like people. You know, they have this image of like the mob, like, oh, we don't go after women. We don't go after children. It's like maybe at one point that was true. It depends on what time you're talking about the mob, because the time that we've been investigating around, around this time period, like Murder Inc.

Time period, the early history of the mob, they don't seem to really care all that much. Uh, another possibility is that [00:36:00] somebody, maybe she had some of Jack's money or people, somebody perceived that she had his money and it was just. Oh, let's kill her and take the money. I mean, uh, again, it all that this is such a rough and tumble time in American history and such a violent time in history.

Oh no, I just, you mentioned a rough and tumble time in American history. I'd recently watched, uh, been watching the movie Once Upon a Time in America and James Woods. Uh, character Maxey has a good line where, uh, They're arguing with, uh, it's a labor organizer and, uh, and, uh, James Woods's character says, well, the country's still growing.

Uh, some diseases are better to have when you're young. And he responds like, you guys aren't like a disease. You're the plague. But you, in a lot of ways, it's like, it's like a country growing up. It's like a child, right? Like where, like this early version of organized crime, I guess you could be like, oh, this is like a case of the measles or what have you.

Like you're better off [00:37:00] just to get it out of the way. I mean, we don't do that now, but you know, back in the day they used to have like chickenpox parties and stuff like that. And so you would just get it out of the way in a lot of ways. Like, yeah, like this early version of, uh, organized crime is, it's inevitable it's gonna happen.

Happened for a country that's growing up. Also a country. We, we've really focused on this whole podcast about the crime part of it. Not so much about the punishment, but the, in the us the it, it grew up so fast during this time period of the late 19th century, in the early 20th century. A lot of systems never got put in place, and I think even a hundred years later, we're still sorting out the fallout of that, that there's systems got built up really quickly to deal with this plague of violence.

And maybe they weren't the v the very best systems that to be put in place where other countries that were more established like. [00:38:00] Britain had a police department for a lot longer in London and in the towns, and they had a more of a theory of policing and other places had more of an idea of policing in the US It was really either, you know, we talked so much about the Old West and the the sheriff and, but uh, they were still trying to figure out policing in much more violent places like New York City and Chicago and these big cities.

They're trying to figure out how are we going to have law and order, and we see that that's how, uh, American, the whole American idea of law enforcement comes out of this time period. Because really beforehand, there wasn't a huge need for law enforcement. It could be more ad hoc. Yeah. Really. I mean, this, at this time period, this is kind of where the FBI comes about, and Jagger Hoover kind of enters the picture and you get this idea of like [00:39:00] scientific policing.

I, I recently, uh, last night I watched a little bit of this movie, uh, public Enemies, which is about. It's the Johnny Depp one with, uh, he plays like John Dillinger. Yeah. And that's like a big theme in the movie. It's like the early history of the FBI and like, uh, Jagger Hoover is like, you know, arguing to judges and senators and, but why we need an organization called the, like the fbi.

I, it's crazy to think like, people just take it as for granted now, like the FBI's there, but not that long ago. Like, You know, people, I guess, I guess they would all be dead now, but you know, some people would still, they would've been really young, but had maybe just recently passed away where it, it was a legitimate argument where I.

Do you need something called, like, do you need something like the F B I? Like it seems like it's rife for all different types of problems, um, and had to put forth a good argument for why you needed a Federal Bureau of investigation. Um, But like you were saying, [00:40:00] like it's growing pains, like you didn't really need this type of stuff until, you know, crime became more organized.

Now let's wrap up the story today of Jack Diamond. Why do you think he was worth spending some extra time on, and what was his real connection to Murder Inc. Well, you know, like I pointed out earlier, like Jack was the bodyguard of Arnold Ross scene. He was the bodyguard of little Augie. He ran one of the most like successful bootlegging operations during prohibition.

He was shot at least 10 times and finally killed in the conspiracy maybe involving a police department of Albany. Like how many gangsters can say they did all of that. Like, that's a, that's, that's insane. That's just a crazy story. Like, and I just thought people would really enjoy it, you know, like I.

That's not even including the crazy trip to Europe that we talked about. It's like, you know, you know, kind of wrap 'em up and like, in conclusion, Jack, [00:41:00] I don't know, he's just one of the more, it has one of the more insane, fun gangster stories of all the ones I've, uh, investigated so far during this time period.

And in, in relation to Murder Inc. Um, I mean, he was little augie's bodyguard. Right. And then we learned basically in a lot of ways, the labor, slugger war, that involved, uh, Leke and Jacob Shapiro, uh, in some ways kind of created Murder Inc. So it's all connected really. And I just thought this would be a fun sidetrack episode was, and, you know, kind of take a little break from Murder Inc.

And, uh, Investigate this guy's story cuz as soon as I read it, I, I think I mentioned it on the episode, like we, we gotta do like a little kind of short episode about this guy cuz it really is a crazy, I, I don't loosely use the term fun, but it is a fun story. I mean, this guy was a ruthless killer and drug smuggler and bootlegger and murderer and womanizer.

You know, [00:42:00] it's not a fun guy, but. It is a fun story and I think it is interesting to learn more about some of these side characters who they don't, they're maybe not gonna get put up on the marquee, but he really was an important part of this story of Murder Inc. And as we go back and get back into the stream of the narrative next time, keep people like this in mind because it, it took more than just.

Meyer Lansky and Albert Anastasia and these people at, at Dutch Schultz, there was a lot of people involved. Oh yeah, for sure. You know, and I just, like I said, I just think the audience would just get a kick at over reading this guy's story. Like he was shot 10 times, like multiple times, like near the heart.

He was like dating movie, the equivalent of movie stars at the time. Like, you know, it got kicked out of how many different countries in Europe for whatever odd reason he thought that was gonna work. And you know, he has such a. Maybe he was killed by the police. [00:43:00] Like it's just such a crazy story and is I just thought people would enjoy it.

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