In the roaring 20s, debonair jewel thief Arthur Barry swiped millions of dollars worth of diamonds from some of New York's most affluent residents. Barry's audacious and no less ingenious burglaries seemed the stuff of detective fiction, earning international attention. Today, we're joined by Dean Jobe, the best-selling author of A Gentleman and a Thief.
a new biography of Barry, and a New York Times editor's choice. Dean specializes in historical true crime, and his previous books include The Case of the Murderous Dr. Cream and Empire of Deception. Check the show notes for a link to his website where you can find out more about his work. Dean is also Professor Emeritus at the University of King's College in Halifax, Nova Scotia, where he teaches part-time in the Master of Fine Arts and Creative Nonfiction program.
In addition, Dean has worked as a journalist, writing for such publications as the Chicago Tribune, the Irish Times, and the Toronto Star, among others. Today, we'll hear how Arthur Barry mastered jewel theft. how he earned a reputation as a gentlemanly burglar, and how his most notorious heist led to his downfall. This is The Art of Crime, and I'm your host, Gavin Whitehead. Welcome to a special author interview episode of Crimes of Old New York, A Gentleman and a Thief.
Well, it is my pleasure to introduce Dean Jobe. Dean, welcome to The Art of Crime. Thanks for coming on. Oh, thanks for inviting me, Gavin. Let's dive right into it, shall we? So Arthur Barry is born on December 10th, 1896 in Worcester, Massachusetts. And Barry falls in with a bad crowd at an early age. By the time he's in his teens, he is already associating with career criminals.
Most notably, he works for a guy named Lowell Jack. Who is Lowell Jack, and what does Barry do for him? Well, Barry explained that, yeah, as a teenager, as a juvenile, He racked up a bit of a record, and he always said he was big for his age. So it just meant he started hanging around with older kids. But he also started hanging around with this fellow, Lowell Jack. And Lowell Jack...
was retired, but in his heyday, he was what was called a yegg man. And that was a term we don't hear anymore these days, but that was a safecracker. And as he'd gotten too old to scamper in and out of... out of banks and businesses to blow their safes, he took to concocting nitroglycerin for other younger Yegg men to use. And he needed someone to distribute this in New England. And Barry had delivered food, a little job he'd had to Lowell Jack's house. He hired him.
And there's a great scene that Barry remembers of the first time he did one of these errands. He was handed a suitcase, and he would find out later there was a bottle of nitroglycerin inside, packed with... cotton to cushion it. And all Lowell Jack told him was, you know, here, you know, deliver this, be careful with it, and, you know, try not to drop it.
So very precious and dangerous cargo that he was entrusted with as a teenager. So after repeated scrapes with the law, Barry winds up in the Massachusetts Reformatory. However... In 1917, he pursues what many would have seen as a nobler calling. He volunteers to serve in the First World War. And he is assigned the position of First Aid Man.
What is a first aid man and what do they do and how did Barry perform in this role? Well, today we know them as medics. These are first responders on the battlefield, if you will. I mean, they were sometimes kidded as somehow not being brave enough to fight. But the role of these first aid men was to be basically in the footsteps of the men with guns when they went over the top.
into no man's land on attacks, and they would start treating wounded men where they fell. Barry and his colleagues are taking all of the risks exposed to to gas, to bullets, to shells of any man with a rifle. But their job was to patch up the men on the battlefield as well as they could, and stretcher bearers would come in their wake to take the men back.
And they would go forward. So really, it was an incredible act of bravery. And the casualty rate among these first aid men was atrocious. Because as I said, they're... They're out there unarmed, exposed to the same risks as any soldier. Do we have any specifics about how Barry performed in this role? Well, in one major battle...
He was so brave under fire, one man who was badly wounded and ended up having his leg amputated but survived was only because Barry had carried him off the battlefield under fire. At other points, Barry was wounded. He was shot or wounded with shrapnel. He also was gassed and was out of action for weeks while his lungs recovered. But in this particular battle, he had acquitted himself so bravely that he was recommended for a Distinguished Service cross.
Oh, this is one of my favorite parts in the whole book, because, yeah, he must have acquitted himself quite well if he was going to, if he was slayed to receive this award. But what happens there? Well, part of the subtitle of the book is Jazz Age Rogue. Barry always seemed to have a way of playing the role of the rogue. And what happened is he never received the medal because he went AWOL. And as he was recovering in hospital in Paris...
He went on a frolic with another man who was in hospital, and they ended up going to the Folies-Bégère and other highlights of the nightlife of Paris. He was actually able to blend back into his unit and was never prosecuted for being AWOL, but it meant that when he was supposed to receive the medal, he was nowhere to be found and never received it.
Come on, Barry. AWOL during your own awards ceremony? That's bad form. Well, as we'll talk about, he knew how to enjoy himself. Did he make some wisecrack about it later in life, too? No, exactly. He was interviewed about... Yeah, about 15 years later. And he said, yeah, I just said, yeah, I'm not sure why. I never received that award. Of course, he knew very well why he hadn't.
So Barry comes back to the U.S. in the fall of 1919. And like many of his fellow World War I veterans, he is unable to find a job. And this is why he actually resorts to crime in the first place. After thinking over his options, as it were, he makes up his mind to become a burglar. You write, quote, The Roaring Twenties was a perfect time to launch a career as a thief of distinction, unquote. Why do you say that?
Well, in 1919, when he comes back and tries to find work in New York, the 20s aren't quite ready to roar, but very soon after they do. And it's a good time to be a thief because... As the 20s take off, as the stock market booms, as a whole new consumer economy is created in the wake of the war, and people are living it up, there were a lot of wealthy people.
And one of the ways they liked to show their wealth was to flaunt their jewelry. And that meant if you were a discriminating thief and burglar, as Barry aspired to be, you could make a pretty good living. And it was interesting how he decided to become a burglar. He'd had some luck doing break-and-enders as a juvenile, because he had, as you said, gone to Reformatory and had a juvenile record. But he actually remembered...
thinking of his options, and he thought, well, I don't want to rob banks. I'd need accomplices, and that's kind of dangerous, and I don't want to mug people on the street holding a gun at them because that's somehow impolite. But sneaking into their houses, sometimes when they're not around, other times when they're sleeping, and swiping their jewelry wasn't a victimless crime by any means, but...
It was more, again, of a gentlemanly way of making your living at crime. So you've said a little bit about jewelry and people's readiness to flaunt their jewelry. There is a lovely... passage in your book where you talk about the social and cultural significance of jewelry in the jazz age. And at one point, you dwell on the writing of F. Scott Fitzgerald, whom you call
quote, the leading chronicler of a wealth-obsessed decade, unquote. What does jewelry represent to Fitzgerald, at least based on his fiction? Fitzgerald has a story that I had in mind and I mentioned in the book, where... Two kids in boarding school, one wants to, they try to impress each other with the wealth of their families, and one blurts out, you know, well, my father has a diamond as big as the Ritz, Ritz-Carlton Hotel.
Obviously an exaggeration, it's an 11-story city block-sized hotel. And the story is called A Diamond As Big As The Ritz. But it really spoke to the fact that this was... This was kind of the ultimate status symbol. And one way I like to think of it is, you know, you can have a huge, expensive mansion, but you can still live in it. And you can have...
a sports car, a high-end sports car with hundreds of thousands of dollars, but you can still drive it. But there's only one thing you can do with jewelry, and that's show it off. You know, it could be sentimental value as well. But really, it is the ultimate, you know, bling is the ultimate statement of wealth. And that's true now, and it was true a hundred years ago. And one police captain in New York even said that...
because Barry wasn't the only jewelry thief operating in the 1920s. Jewelry theft was quite a common crime, and this police captain was so fed up with having to investigate it. He said it would help if... You know, if society women weren't running around looking like a pawn shop window. After a quick word from our sponsors, we will be back to talk about Barry's illustrious career as a jewel thief.
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He comes up with a sophisticated way of planning and carrying out his burglaries. And I kind of want us to talk through his MO step by step now. He has a number of strategies for identifying whom he would target for his next heist. And one of those strategies involved the society pages of New York newspapers. In fact, Barry refers to society calmness as his unwitting accomplices later in life.
So what kind of information could you find in the society pages of 1920s newspapers? And how did Barry turn that information to his advantage? Well, I read this comment he made about how he used the pages. So, of course, I went... back into the newspaper archives and started looking at society pages. And they were filled with tidbits. Who was wintering in Palm Beach? Who was coming back in their private rail cars?
who was having a party on Long Island or at Newport, Connecticut. Basically, it was a roadmap, if you will, for someone like Barry, who's trying to think of... Well, you know, these are the prominent people he's looking to target. Very valuable to know who's in Palm Beach because their jewels aren't going to be at their home in Long Island. And if there's a party, well, maybe he can crash it and we can talk about that. But as well, the Society pages had these very helpful photographs.
of wealthy women in their jewels with strands of pearls worth hundreds of thousands of dollars a century ago, millions now. And yeah, so very helpful for a guy who's just trying to figure out... who his targets are. The other thing he claimed is he'd memorize the social register. This is impossible to memorize. This is hundreds and hundreds of pages, like a telephone book of the rich and famous. But it listed...
addresses, names, connections. So he could use the social register, which was freely available. Again, how people showed off their wealth. They wanted to be in the social register. And he could... basically cross-index that with the society pages and start figuring out who was a likely person to target next.
Another one of his strategies involved a nice outing to the Central Park Casino. Could you tell us about this one? Well, a casino in those days wasn't, we think of it as gambling now, but it was just any sort of... restaurant, especially one that had patios and in a setting like Central Park. The Tavern on the Green is a successor to that. And this is where a lot of wealthy women would lunch.
So Barry developed the idea of just sitting in the corner having his own lunch and sizing up who looked like they were wearing very interesting jewels. And if he saw a likely target, he would discreetly follow them into the parking lot and see what limousine they got in and drove off. And then he got really ingenious. He'd go to a phone, call the police station.
say he was Patrolman Schultz or Patrolman Smith, some name, and say, look, there's just been an accident. I'm trying to trace this plate. Can you tell me who it is? And they would do it. No one questioned. So he actually was able to use this several times to figure out where someone lived who he now knew had jewels. And he would simply then start casing and staking out the...
The mansion or estate the person lived in, figuring his next move on when to break in. Yeah, there's definitely some ingenuity involved in this MO. It's hard to deny, right? Well, that's one of the things that drew me to this story. He was very clever. I mean, later jewel thieves, some would emulate some of what he was doing. If he didn't invent some of these strategies, he certainly refined them and was very successful with them.
He also exploits human nature quite adeptly, doesn't he? Because he knows that no one will ask questions about... whether or not he is who he says he is on the phone. And you mentioned in your book that for that reason, he kind of has some of the qualities of a con man. In those days, like now, there can be signs outside saying premises protected by alarms.
And he always, he later on said, you know, I was always grateful for that. Because then he would just put coveralls on, pretend he was from, have a made-up card from the alarm company, and say, we're here to do the annual check. And then when the servants or staff would dutifully send him to whatever compartment the controls were at, he'd either disconnect the wires of the windows he wanted to come in.
Or bend back, it's like an old-style alarm clock with a hammer and a bell. Bend that back so it wouldn't ring, knowing he'd now deactivated the alarm system. So yeah, like a con man, he exploited that trust. He also, several times, would don a tux and crash a garden party or a... a party at a mansion and this is where i could not get away from the fact that it was just like a great catsby so you've got people as in that novel which was written right at the time barry was doing all this
people showing up at the parties at these mansions, some of them not having a clue who the host was, not really knowing why they were there. And it was easy for Barry to just mingle and blend in. He was a working-class boy from Worcester, but he could emulate an accent or the speech of a very refined person. So again, again, impersonating.
and could pass himself off. And of course, he could drop names pretty adeptly because he kept track of who was who. He's very chameleonic, right? Able to have different identities and exploit the trust of others. Every good con artist is also a good actor, right? We've talked a bit about how he identified his targets. So once he's done that, he typically cases the residents, learns the routines of, you know, the comings and goings and all of that.
Then eventually he commits the burglary. So what are some of the ways that Barry was able to enter the houses he robbed? And I wanted to dwell on this a little bit just because it seems like the way that he got into the house was so essential to his identity. as a criminal. And then once you talk us through that, how did he go about swiping the loot? Well, I mentioned that one of the ruses he used was to put on a tux and just blend into the party.
He would then take advantage of being in the house to steal away upstairs. And his cover story would be, well, I'm looking for the bathroom, or if someone caught him, he'd pretend he's drunk. But what he's doing is going from room to room. looking in bureaus. There probably aren't jewels there because they're being worn downstairs, but is there a safe? What's the best window to come in? He's basically committing the layout to memory. And then...
coming back at a better time when Jules might be there to actually do his theft. He's concentrating his efforts on two areas. One is Nassau County, Long Island, which was the... The kind of mansions that featured in Great Gatsby. Fitzgerald was living amongst the millionaires of Long Island when he wrote that novel. Also Westchester County to the north of Manhattan. White Plains, Rye.
uh, the, uh, Yonkers areas that were really, there were some really, uh, wealthy enclaves there. In one of these areas, he was known as the dinner thief because his MO was. to break in at dinnertime when everyone's downstairs and noiselessly rifle through bedrooms, get the jewels, and leave. I became known as the ladder thief in Long Island.
a similar M.O., but he'd never bring a ladder. He'd always just borrow one from the estate or the neighboring estate and use that to get into a second-story window or climb a trellis, climb a porch. But he wasn't an opportunistic thief. He was very careful to know. He wanted things to be very precise. He would watch for police patrols to get the sense of when the police might be there. And incredibly...
While he sometimes used his own car as a getaway car, he would simply go to the nearest train station, jump on, and go back to Manhattan where he was based. So he knew the train schedules really well. I mean, he was an extremely, extremely smart guy, you know, to play the roles he played, but also just to innovate and come up with so many different ways. Two things that stood out. One is, he said...
He always worked when there was no moon. Either the moon had set or it was a new moon. And when I was compiling a list of his either suspected or admitted burglaries, I... couldn't believe that they were all like four in a row one summer, were all at the end of the month. I checked on the internet, those were all nights with no moon. So that's what he did. So he was very careful that way.
He also just made it a point of being very careful about his targeting that he had his escape routes all set up and would hopefully be able to get in and out without being detected. And then just to be really clear about this point, because you mentioned that he would sometimes break into houses while families were eating dinner.
They would be eating dinner downstairs. He would procure a ladder from somewhere outside and then enter by way of a second story window and then steal the jewelry or whatever. from that second story without the family knowing that he was even present in the house and then he would make his escape. And another name for what he did was Second Story Man. Exactly. That was his way to get in.
Doesn't it come from the title of a play? Yeah, there was a play at the time. So the second story, man, like Yigman, was a well-known term. Yeah, it was instantly recognizable to people. His kind of crime was the work of the second-story man, someone who could sneak in and sneak out of your house. Well, another thing Barry did was, every once in a while, despite all his planning,
a maid. In a few cases, a maid walked in, not knowing, you know, the family's downstairs. He thinks the servants will be too. And in one case, even though he's a burglar, he was dressed so well. with his hat and everything, that when the maid walked in, he simply turned and smiled. And the maid thought, oh, I'm sorry, sir, thought it was a guest that she didn't know about, and backed out. And he continued to smile, grabbed his hat.
jumped out the window. Only then, when she recovered from her shock, could she raise the alarm. And by then, he's halfway across the lawn. I don't think Michael Jackson knew it, but he wrote a song about Arthur Barry. He is the original smooth criminal. you know but i also wanted to bring up that term the second story man because as you mentioned it is like yank man it's it's so funny to me that there is a kind of like
I don't know, early 20th century taxonomy for all these different classes of criminal. And most of these are terms that we are completely unaware of. these things. But I think it's also one thing that I really enjoyed about your book is how you work in all of this period diction, slang, and so on and so forth. It does kind of help to immerse the reader in that period. Yeah, I mean, I want to be careful either by context or explicitly to explain what they mean, but it does the error.
Another thing that we could talk about is, why was Barry stealing all these jewels? I mean, by my estimate, today, $60 million worth over seven years. And he's fencing these jewels and only getting about... 10%. But he's what's known as a plunger. Now, there's a term you don't hear, but it's a very logical term. It's someone who plunges into the nightlife of especially Broadway.
New York, Barry had a gambling addiction. He said he preferred gambling to sex. So he would make some money, but he lost a lot. And when he had a big loss, he'd have to do more stealing. You know, he dated showgirls, he knew all the speakeasies, he mingled with the sort of the Runyon-esque characters that became the hit show Guys and Dolls.
And he really lived that life. But plunger was a term, yeah, that it was funny to go back and see a term like that. Again, everybody knew exactly what it was. So Barry plunged right into New York nightlife. And the way he explained it was, look, it was the times. There'd been so much death and destruction in the war. There'd been the horrible Spanish flu pandemic. Millions died. People wanted to live it up.
And that's what he said at one point. He said, look, you know, I squandered all this money. I never, I wish I'd saved some. I never did. You know, he said later, because he was always suspected he had a stash somewhere.
But he said, look, it was the times. Why not live well? Lose everything in a game of craps. You got to go plan your next jewel heist, right? So. We have established beyond question that Arthur Barry was a master thief, but as the title of your book suggests, he was also a gentleman.
And we've gotten into a little bit of this already, but maybe you can say a bit more now. What was it about his personality that marked him as a gentleman? Why was he able to blend in with the very people he was trying to rob so easily? Well, two aspects. One was just how he comported himself. As the years went by, I mean, he could read the news. Well, he read the newspapers, obviously, very closely. He could read about his robberies, his burglaries.
And he would often say, and the press would taunt and say, oh, you know, thousands mourned jewels were left behind or were in a safe or, you know, as if this showed his incompetence. All it showed was he didn't know about them. But this made him realize he was leaving a lot of potential money behind. So he decided that maybe if he got a, he recruited an accomplice, a childhood friend.
and even worse juvenile delinquent when he was young, named James Monaghan, who had a suitable outlaw named Boston Billy, like right out of the Old West. But he gets Monaghan to help him, and that's someone who can... rifle through drawers and things. Barry's role became, well, what they would do is they would break in even while people were home and right into their bedrooms. And Barry's role was to soothe them. So in some robberies...
He famously came into one and said, how was your night at the opera? You know, it's like he was just meeting them on the street where they were old friends. And he said to another woman, you know, don't worry, don't worry, we're just here for the jewels, we're not going to hurt anyone. And his accomplice, meanwhile, is rifling through the jewels. And so this is, the press started calling them, gentlemen thieves.
You know, like, this was a new thing. Nobody really was that nice about it. You know, like, don't worry, we won't keep you long. We're just going to take all your valuables. See you later. So there was that aspect, but also the... The actually dressing up like a gentleman, acting like a gentleman, taking on the persona of a gentleman to case the houses. And another thing Barry did is, as he circulated in these parties like another invited guest.
was he started seeing who was wearing what jewelry for, perhaps somewhere down the road, another heist. There is no better example of Barry's ability to fit in with elites than his encounter with the Prince of Wales, later to reign as King Edward VIII. Can you tell us this story? How does Barry meet the Prince of Wales and what do they get up to? Well, the Prince of Wales visited Long Island in the fall of 1924, and he was there on an unofficial visit.
But as I say in the book, the Prince of Wales, the future Edward VIII, was really the first royal celebrity. The press coverage was incredible. Every little tidbit, exactly the kind of royal coverage we're used to. But, you know, his father, Edward VII, wasn't quite as much of a playboy by any means.
I mean, the prince was the most eligible bachelor on the planet. Even though he was trying to relax on Long Island, there was intense media attention. But he was there to play. I mean, he went on yachts of rich people. played polo on their lawns or played their private courses. And one of the wealthy people who hosted him on Long Island was Joshua Cosden, who was an Oklahoma oil man who'd struck it rich.
and had ingratiated himself into New York society. And he had the ultimate coup. He and his wife had the prince come to a party. And Barry, of course, was very attracted to this crowd. This was another new thing. And crashed the party at the Cosdens.
He never said whether by design he went out of his way to meet the prince. He would have recognized him. Everybody knew what he looked like. His picture was in all the papers. But he goes over to a punch bowl, is introduced to the prince as Mr. Windsor, as if nobody would know. He's going by the name Dr. Gibson, although no one ever asks what he's a doctor of. And they start to get along, and the prince suggests he'd like to steal away and really see Broadway in New York.
you know, really have a night on the town. And Barry offers to be the guide. And some of the people around the prince put dampers on that and say, no, we shouldn't. But then the prince seeks out Barry later at the party and says, And I love this line, which was quoted at the time. You know, Dr. Gibson, is that little lark still on? And Barry takes them to some speakeasies and nightclubs on Broadway.
They take in the shows, they take in the bands, and by Barry's accounts and dribs and drabs that came out later in the press, had a royal time. night on the town. And then a few nights later, Barry breaks into the Cosden mansion, which because he crashed the party, he knew the layout. not only steals the costs and jewels from the Cosdens, but their house guests were Lord Louis Mountbatten and his wife Edwina Mountbatten.
and he stole tens of thousands of dollars worth of jewels from them as well. So they were the prince's cousins who were part of the royal entourage, so he was even able to steal from royalty. There you go. I mean, and the Prince of Wales could not have found a savvier plunger for this lark, right? Correct. Yeah, it just goes to show that business and pleasure were not too far apart from each other for Barry, right? It's crashing parties. He's working.
Yeah, that's right. And he did kind of relish the idea that, you know, the child of Irish immigrants could pull one over on a member of the royal family. Barry earns a reputation as an American raffles in the press. So once he's pulled off a bunch of these heists, journalists start kind of referring to him as a raffles.
This is a reference to a character named A.J. Raffles. So who is that? Who is A.J. Raffles? And what is his place in American and British popular culture in the early 20th century? Between interviews and a sort of an assistant, a biography that was written about 40 years ago with his cooperation.
At some point, Barry said, you know, he kept seeing all these headlines, you know, Raffles strikes again, you know, Raffles robs Long Island House. And he wondered who Raffles was. So he went to the public library and got a book out. And Raffles, this A.J. Raffles character, turns out to be the creation of E.W. Horning, who is the brother-in-law of Arthur Conan Doyle, a British writer, who created this upper-class character named A.J. Raffles, whose...
fallen on hard times, and resorts to jewel robbery to make ends meet. But like Barry, he's gallant, he's got a code of ethics. For instance, it's okay to go to a country house. and steal but you don't rob you don't rob the host you only steal from other guests he walks this line between is he a good guy or a bad guy you know do you you root for him You can root for Barry. So it was a very apt comparison. And again, at the time, the Raffles stories were early 20th century in the 1920s.
Barry's time, he was one of the few people who probably didn't know exactly what a raffles was. Like I said, you could confidently put it in a headline and everyone knew what you were talking about. And if memory serves, you point out in your book that several really noteworthy actors portrayed raffles on stage and screen. Is that correct? Well, Ronald Coleman was one.
And Barry looked so much like him that it was remarked on at the time and later, a star that nobody really knows. Now, Basil Rathbone, who played Sherlock Holmes famously, was another Raffles. And David Niven reprised the role in 1939. So yeah, and the character became, after Barry's time, became like a staple of movies.
It's so awesome that Basil Rathbone played both A.J. Raffles and Sherlock Holmes. There's a terrific line in your book. I think it's a quote from the New York Times, and they refer to those characters as brothers-in-law because... The author, the inventor of Raffles is Conan Doyle's brother-in-law. Yes, Raffles and Holmes were literary brothers-in-law. That's right. Something like that, yeah.
So you've touched on this a little bit already, but I want to pick your brain about it a little more. So, I mean, I'm always fascinated when notorious criminals are kind of compared to fictional characters. What, if anything, does this comparison to Raffles reveal about the public perception of Barry and his crimes? Well, I call Barry a rogue, but, you know, you could call him a rascal, too. The fact that he...
He didn't threaten, well, I mean, it's threatening to have a guy in your bedroom saying he's robbing you, I realize. But, you know, he didn't harm his victims. Emotional harm, yes, not physical. And I'm not trying to justify what he did. But, you know, this is at a time when robbers are going into the Diamond District of New York, guns drawn, shooting anybody in their way. So...
If you had to decide which of those classes of criminals I'd root for, I think you'd be on Barry's side a little more. When things go south for Barry, and he is exposed as a ladder burglar, dinner thief. gentleman thief, there isn't exactly an outpouring of affection, but there is a very clear sense of, well...
You know, he's like a Robin Hood who stole from the rich and gave to himself. I mean, he was one step, almost only one step away from a Robin Hood, that he did target people who could absorb the loss. And coming into the depression, you know, when banks and rich financiers who are blamed for all of the hardship and economic turmoil. of the hungry, the dirty 30s. You know, a character like this gets a pass pretty quickly in terms of his ethics because he's targeting...
Arguably, by then, he's seen as targeting people who are bigger criminals. We're going to take another quick break to hear from our sponsors. And when we get back, we will talk about maybe Barry's single greatest heist. In 1927, Barry carries out a theft that he later refers to as his quote-unquote masterpiece. This is the robbery of the Livermore estate.
What happens during this break-in? And I should mention, as you pointed out earlier, Barry has started working by an accomplice named James Monahan at this point. Yeah, Barry used the term masterpiece. It's not the most lucrative. heist he did. It stands out partly because it turns out to be his last heist. He doesn't realize that at the time, obviously, but it's not long before...
He is arrested and ultimately exposed as this one-man crime wave who's been hitting Long Island and Westchester County for years. The Livermore robbery was like something out of a movie. He and Monaghan go in. They wake the Livermores. Jesse Livermore is a Wall Street plunger, another form of plunger. He's a guy known to have made and lost several fortunes by this time on Wall Street.
touted as sort of a genius, the boy genius of Wall Street. It's kind of interesting that the boy genius of Wall Street would meet the boy genius of Jewel Thieves. So, room's dark. It's not clear whether Barry's got a gun, but Monaghan probably does. They say, calm down, we're just here to get the jewels. And they're wise to the fact that a lot of jewels are being kept in safes. So they want to know the combination of the safe.
livermore says he can't remember it and the wife his wife jesse uh sorry not jesse uh dorothea livermore can't remember it either so almost a comedy A comedy skit starts playing out. Monaghan goes out to get a chisel and a hammer to break it open. There's silence, and to fill the silence, they start chit-chatting. And Dorothea Livermore starts to think, well, maybe I can play this gallant.
burglar. Now, he's already taken what jewels were lying around, and it's quite a valuable haul. He thinks there's more in the safe. But he's taken a couple of pinky rings. And she says, well, you know, Papa, she calls her older husband, Papa, gave me this one, and I gave him that one, and they have sentimental value. You know, could I get them back? And he gives them back. So...
What could be more gallant? He even said later, you know, other jewel thieves are going to think him crazy. I mean, these were tens of thousands of dollars. And he gave them back. He'd also, they'd also earlier robbed the house guests in the next room. And when the woman looked like she was in distress, he'd actually gone and fetched her an aspirin and a glass of water. So this whole thing plays out like a parody of a robbery.
To the point where after Barry starts giving stuff back, Monahan says, let's get out of here while we still got some loot. Because they do break into the safe and it's empty. This, of course, the headlines are just outlandish. And it's so... wild that a detective named Harold King, who'd been systematically trying to hunt down this mysterious burglar, when he comes to investigate, at first, he doesn't believe it. He thinks...
This must be an inside job. And finally comes to realize, no, they're being genuine. This sort of farce had played out in the bedroom. And Barry's reputation is cemented as this gallant burglar who would even give jewelry back to please a lady in distress. And it's so interesting to me that he refers to it as his masterpiece because, as you've made clear, others would call it a parody or a farce. So I'm wondering, like, why do you think he calls it his masterpiece?
Well, I think, you know, maybe he was stretching the term. I think what he meant was it's sort of like his most notorious burglary or his most high profile or signature. Maybe he should have said signature burglary. No, I'd say the Cosden was a masterpiece. Stealing from royalty, that was a, and he, and actually he was never charged with that crime.
And only decades later did he actually fess up. He was suspected of it, especially after he was caught. And it was realized he'd done a lot of these burglaries. So it might have been as well that at the time he was being interviewed about it.
That was the big robbery everybody knew. The other ones, he was being cagey on. He was too worried about being charged with him, so he didn't let on. It's also possible, too, it occurs to me that he was just being ironic when he called it his masterpiece because he does...
He does have a bit of a sense of humor, right? This is the same guy who was AWOL during his award ceremony. I was like, yeah, why didn't I ever get that medal? Yeah, and at one point he's being interviewed and he said, you know, I don't know how I feel about...
talking about all the tricks of the trade. I really hate someone to follow in my footsteps. And then he outlines all the things he did. So, yeah, I think he had a sense of the irony of a lot of the situations he was in, that's for sure. And I think... That aspect of his character also makes him a little bit of a lovable rogue or a rogue who is easier to love than, say, the violent criminals you were talking about earlier. Ultimately, Barry's masterpiece leads to his downfall.
Because his great nemesis, the police investigator Harold King, whom you mentioned a minute ago, manages to collar him and our beguiling raffles is thrown in the clink, alas. But this should come as no surprise. Barry's story is far from over at this point. In fact, the story takes an almost unbelievable number of hard left turns from this point. But this is where we will leave Barry for today. And before you go...
Dean, I had one last question for you. On your website, you describe this book as The Great Gatsby meets Catch Me If You Can. We've already said a bit about F. Scott Fitzgerald, but I wanted to return to him and the great Gatsby as we wrap up this interview, because it struck me that you cite Gatsby quite a few times throughout the course of your book, and it seems like it was a really...
like important kind of touchstone as you were conducting your research. Did spending so much time with Arthur Barry and his world, his milieu, give you a richer or... a new or a deeper appreciation of Fitzgerald's novel? And if so, how did you come to see the book differently? Well, The Great Gatsby is essential reading. I did a book about 10 years ago called Empire of Deception about a con man in Chicago. The first time or second time I had read Great Gatsby. And I just found so many...
echoes of real life. And I mean, that's why I describe Fitzgerald as such a great chronicle of the jazz age. I mean, when it came to capturing jazz age excess. He spent the summer of 1924 on Long Island staying in a small house near a mansion, if this rings a bell. In other words, he's Nick Carraway to Jay Gatsby.
And so much of it rang true. And I don't know how many times I've read the novel now. I find something new in it every time. And a lot of scholars have extracted that Meyer Wolfstein, the underworld character that... that Gatsby introduces Nick Carraway to, as described as the man who fixed the 1919 World Series. Well, that's Arnold Rothstein, a real person. Just so much.
of the novel is is not only of the times but chronicles the times and of course it's such a great cultural touchstone i mean it's like an artifact that helps me tell this true story uh because of of the fact that this great novelist has had a ringside seat to the jazz age. So who better to evoke or turn to for a pithy quote or just for a...
for context, because it's not like he was writing in the 50s even remembering his Jazz Age escapades. He was very much... in that world and seeing it well like nick carraway was you know his fitzgerald's famous line the you know the rich aren't like you and i and the whole idea of the uh you know, the carelessness of the rich that he talks about at the end of Great Gatsby. You know, you see echoes of that in the real life of the elite of New York that buries targeting.
You mentioned a moment ago that every time you return to the book, something new leaps out at you. I'm wondering, is there like a concrete example of something new that like a new scene or a scene that you appreciated differently when you were working on this book? Well, when I read it for Empire of Deception, I was looking for references to con men. So when I read it for Barry, I was looking for references to jewelry, primarily.
Just the garden parties and things, especially with Barry, I mean, that resonated because thinking like he says it's really easy to sneak into these parties. You know, I write nonfiction. I mean, I know what he told me, but does it make sense? It's like the business of Israel Moon. Whatever I can check, I can check. And if you read Greg Gatsby, you see that, yeah.
at least in Fitzgerald's experience. At the time, it was very likely that someone could wander into one of these parties, be accepted, never questioned, and go wherever they want, because... It's a huge party. And if you've seen the movies, either the most recent one with Leonardo DiCaprio or the one with Robert Redford, I mean, yeah, these parties were spectacles.
And as described and as portrayed in the movies. And so that stood out for me, just that it gave some credibility or gave some... confirmation to what barry was saying happened yeah was that feasible or is that you know is that outlandish and it turns out no it was all too feasible Great Gatsby meets Catch Me If You Can. Leonardo DiCaprio is what both those films have in common. I hadn't realized that until just now. Well, I hope he's looking for a new role. That's right.
Well, thanks. That's all I have for you today, Dean. It has been such a pleasure to talk to you. Thanks again for coming on. Well, thanks, Gavin. It's been great chatting with you. You've been listening to The Art of Crime, created, written, and narrated by yours truly, Gavin Whitehead. Liam Bellman Sharp edited sound and composed the score. Last but not least, a thousand thanks to research and production assistant Ken Symphonies.
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