After Dark: Myths, Misdeeds & the Paranormal - Georgian London's Celebrity Criminal

Episode Date: September 7, 2026

What is it about a ‘bad boy’ that we love? That’s as true today as it was in the 18th century. In this episode of After Dark, Anthony and Maddy unravel the extraordinary rise, daring escapes, and final end of Jack Sheppard- the thief who became history's first celebrity criminal...This episode was edited by Hannah Feodorov. Produced by Tomos Delargy and McKenna Fernandez. The senior producer was Freddy Chick.UK listeners: voting is now open for the Listener's Choice Award at this year's Podcast Awards! Click to place your vote on the Spotify mobile app: https://open.spotify.com/s/xhg6PJaSign up to History Hit for hundreds of hours of original documentaries, with a new release every week and ad-free podcasts. Sign up at https://www.historyhit.com/subscribe.You can take part in our listener survey here.All music from Epidemic Sounds.After Dark is a History Hit podcast.History Hit is part of Little Dot Studios, a Certified B Corp™Voting is now open for the Listener's Choice Award at this year's Podcast Awards. Click to place your vote on the Spotify mobile app: https://open.spotify.com/s/xhg6PJa Hosted on Acast. See acast.com/privacy for more information.

Hello After Dark listeners. It is I, Anthony Delaney, one of your co-hosts from, of course, After Dark. Now listen, we have some good news. We have been shortlisted for the top 20 in the Listeners Choice Award category for this year's British Podcast Awards. Now, we made the top, I think it was five last year. So we are greedy historians and we want to make that top five again. This year, things are slightly different though. You can only vote for us in this long list in the Spotify app. And you'll find a link in this week's episode that'll take you to vote for us. As a matter of fact, you can vote for us three times. So if you feel so inclined, please do that. We want to make that top five. We're going to smash it this year. I think we're going to take it, he said, with absolutely no confidence. But lend us your vote and we'll see how well we get on. Heading for the top five, I know we can do it. Jack Shepard, a common thief, became forever immortalized by his legendary escapes from Georgian London's highest security prisons. Shepard repeatedly escaped the clutches of justice and turned every prison break into headline news. Crowds cheered him.

Newspapers followed his every move and his story blurred the line between outlaw and celebrity. But how did a criminal become a national hero in life and a legend of folklore in death? from Georgian London's criminal underworld, welcome to After Dark. Hello and welcome to After Dark, I'm Maddie. And I'm Anthony. And Anthony's... And it's me now, that's going to talk. My notes say everybody loves a bad boy, but I don't.

Do you? Not particularly... I've grown out of that now. Yeah. I'm too grown up. Yeah. No, I just... I was like, does anybody really have the energy for that?

Like, read it in fiction, that's fine. Listen to a Taylor Swift album if you want to hear about a bad boy. Is that, does she think about, she thinks about bad boys, do she? Oh my God. You need a swiftly education. I've actually gone off for so much since the way. Have you? Oh, yeah. Tucky.

I did think about you with that, actually, yeah. Yeah. About how you're feeling about that. I had a lot of unsolicited texts from friends, but was I okay during this time. I know. I had just on news coverage of being like, oh, somebody that was doing detention centers for ice was at the wedding and all this kind of thing.

She built supposedly like a castle. I don't have to unquietly like she's here. She's never going to hear. She built a castle inside Madison Square Garden. I mean, that's just sad.

Buy a castle if you want one. Can I tell you? Yeah, because she could go to any castle in the world. You can do it. One of the things that I love music. Okay, we are going to do a history podcast in any minute now.

But also a history podcast about celebrity. So this is relevant. Oh, there you go. Well done. She, she, I saw the document. I love a music documentary. even if I don't listen to the music or know anything about those people.

And so I watched her one. See, I hate that, but I have watched it. Do you? But no. And I went, God, you know, she was distributing wealth amongst the crew. And I was like, maybe I've been a little bit harsh. And I was like, well, maybe it was just that I don't like the music. But I quite like the person.

And then this all happened. I just don't know. I think there's an issue of being frozen in teenage years. Okay. That's a problem. I don't know enough, but I'll trust you. Like, let's hope this doesn't find the stuff. It's because this YouTube video will absolutely explode.

I think it can find them. It's fine. It'll make the episode go viral because they'll want to. Anyway, if you have come for the swiftly bashing, please stay for the history. In this episode, we're talking about an 18th century celebrity, someone who was celebrated not for his musical output, but for his criminality and also his particular talent for escaping. Can I just say that there is a book called The Confessions of the Fox and it's about the person that we're going to talk about? I might as well, I don't know why we're here holding back. Jack Shepherd. We're talking about Jack Shepherd, 18th century thief and person.

Now, is this a recent novel? Because on the tube on the way in, I was going over my notes for this, thinking about my research. And I was thinking, I want to write a historical fiction about Jack Shepherd. His life's so incredible, but you tell me it or exists. It exists, but it's a very specific take. It's that Jack Shepherd was a trans man, and it really works in the context. You might be thinking, what? How does this going to work? I think that's very interesting. It really, really works in the context. And it's really good.

It's smart. Okay, I'm ordering this as soon as we're done with this episode. But we're in the 18th century at least, so we're on home brand. Never heard of it. No, I know. Do you know what? I'm not working at the 18th century at the minute. And you're about to not work on the 18th century.

I know. We're both betrayed our true loves. We've gone to opposite ends of the spectrum. though. I've gone earlier, you've gone later. Yeah. Well, and just later, I mean, I'm... And I'm just only just gone earlier.

So we're still hovering around the edges. And I would consider everyone I'm writing about in the 19th century to be 18th century people anyway, so... So we're still... Okay, fine. We love the 18th century. We're in the really long 18th century. It's getting longer all the time, guys. Do you want a bit of context?

Go on, sure. You might as well, yeah. Probably should. Okay, so we're talking about Jack Shepherd. This is a story that takes place in the 18th century, in London, specifically. There are places that you're going to recognise in the story. Newgate prison, ever heard of her? Yeah.

Clark and Wells, Spittlerfields, grimy, busy, delicious places. If you have read my book or listened to the episodes we did on the Cochrane Ghost, Spittalields plays a massive role. And hopefully that will give you some kind of sense of just the incredible atmosphere in this place. You know, this is somewhere that has a yearly fair that has a meat market, there's blood running in the street. There are these sort of medieval windy passageways and roads and these sort of. tenement buildings coming up and there's a very sort of fluid society in this part of London. People are renting rooms. You can slip in and out of different identities and there is a lot of crime going on.

We are largely in 1724, which I feel like is more your territory. You're better on the early part of the 18th century. I mean, if it didn't happen, so 1760 onwards, I like. Yeah, I mean, really 1780. I would pick the 1780s if I had time travel or maybe about 1815. But you're comfortable with this. So we have Queen Anne on the throne 1702 to 1714. And then we have...

She's not, though, on this history, if it's 1724. No, I'm just very true. You're setting it off. I'm getting there. God. And then we have George I first in 1714 until 1727. So he's on the throne during this history. Thank you very much.

Anne has nothing got to do with this. He's nothing got to do with this whatsoever. Well, I mean, he's sort of head of the state. I do. Everyone has this reaction. Everyone has this reaction to Anne. going to try and rehabilitate over the course of my career. It's not going to happen at this next book. I think I just see Olivia Coleman. I know. I can't be

bothered. I know. It's a good film. I think she's a really good politician and I think she's being I think she's being overlooked. Oh God, we're not here to talk about Anna. Anna or Olivia. Anna. And Olivia. Vote for Olivia Coleman for PM now. I mean, sure, we've had so many primis to show me as well. She'll be there next year. Crime in this moment, Anthony Delaney is on the rise. Yes, it is. And there is an equally moral. realistic pushback that's happening at the same time where people are like, we need to reform this society and the Reformation of Manners, is trying to get rid of all that vice from London society particularly. Yeah, it's London in particular. People are moving into the city,

you know, the urban population is growing. And there are a sort of industry, I suppose, that builds up in terms of dobbing people in for crimes, right? Thinking about the thief takers. And these are going to be important characters in our story, this idea that there's kind of, you know, there's no police force as such, but there are watchmen who patrol at night. And if you come across a crime or you're being stabbed to death in an alleyway, you shout for the watchman and hope that they turn up. But also there are these people called thief takers who are more often than not actually criminals themselves and connected with the underworld.

They will kind of identify people who are committing crimes, dob them into the authorities and literally take them, drag them into a prison cell for a price. So this is a system that's very open to corruption. I always think in this period of time that the boundaries of, I don't want to say policing very specifically because there is no police force, but the boundaries of law enforcement, shall we say, are very porous in terms of the world of criminality. And even those people who are the morally, supposedly upright and who are actually just boring old shites, they are using the criminal underclass to infiltrate these spaces to get close to these people so that they can take them down. So, you know, it's a porous situation. And also, crime isn't like, you know, a society now where you sort of think of crime of something that's happening, you know, if you're lucky, somewhere else over there.

It's not something you're involved in. You don't witness it. You don't know that much about it. You don't know anyone who does it, etc. And I think in this moment, you know, what crime is, what is categorized as a crime, and we'll talk about the bloody code in a minute, can be a whole spectrum of things. And it permeates all of life. And a lot of people who, you know, by our monstance, we wouldn't consider to be

criminals are brought before the courts and punished in some way for activities and actions that they've done. The other thing to mention in this period, which is really important to our story, is the booming print media. And I kind of bored of saying this about the 18th century, because if you hear any 18th century historian talk, us included, everyone's always like, oh, print media is booming. It's something that we're just constantly going on about. But it is so important to this story, this idea of the rise of celebrity, that newspapers, pamphlets, ballads, printed images, are appearing on the street, are being exchanged in taverns, sold on street corners, you know, sold in new bookshops, all of this. And so stories, stories, both fiction and real,

about people living now as well as in the past, are just being circulated like never before. And so when people become notorious in the media, they can be put on a pedestal and they become almost mythic because everyone, almost for the first time in society, everyone in that reading society knows who they are and supposedly what they've done. And we'll talk later about the sort of the distance between reported fact and the fictions that are circulated about people and about Jack Shepherd in particular. The bloody code. We should probably cover this. Yeah, so tell me about this. This is almost like honor amongst criminals in its own way because it's, again, It feeds back into this porous thing.

There is a code rather than necessarily laws. There are laws, but it's not necessarily governing. Anyway, bloody code go. That's hard to say. Okay, so this basically refers to a list of supposed crimes and offences that could be punished by death specifically. I'm going to ask you to guess how many. For anyone who follows Anthony on Instagram, he did a video, was it yesterday, about how much you hate when people make you guess things. Guess Anthony Delaney, if you will, how many crimes were listed in the so-called

bloody code for which you should be killed? No, I'm not going to guess because how long is a piece of string? 10, 12? I don't know. Well, you might be surprised to know that. The answer is 200, 200 crimes. These included stealing things, which... There. Well, no, not for death. Not for death. No, sorry, sorry. But like, at least that is a crime, right? Like, that is a crime. Poaching. Sodomy. Yes. I mean, yes.

Cutting down trees. Yeah, well, climate change. Yeah, environmental. Oh my God, have you just listened to, just talking of environmental crimes against nature? The BBC has just done a podcast called Dead Rabbit about hair coursing, which is a massive, just talking about poaching and stuff. It's a huge, huge crime taking place in the British countryside at the moment

that nobody seems to know about. It's absolutely insane. Like, it's a crazy. underworld. Well, I don't know. I think about that. I have consumed this podcast. But what you're saying is they should all be executed. I am not going to answer that, but I'm just going to leave that hanging because I think it is really, really serious and these people are terrible. But no, let's move on. A lot of people who were sentenced to death, though, did not actually get killed. And I think this is important. You know, we've spoken a lot on this podcast about execution days, and we will be

talking about that again in this episode, this idea of the sort of the circus, the hundreds, if not thousands of people would turn up to see people get hanged, that there would be, you know, ballads singers singing about the deeds of these people on the scaffold. A new gate, the bell, the execution bell was rung the night before. There'd be people lining the procession route from the prison to the place of execution. But, of course, I mean, if you've got 200 crimes that people can be arrested for, including cutting down trees, you haven't got the time, the energy, the manpower, to be executing that many people. So a lot of people were transported. Now, at this point in the early 18th century, It is not transportation to Australia, as you might expect, which kind of started up around the 1780s, the best decade, not because people got transported to Australia.

Just to clarify. But it's dead to America, to the Americas. So a kind of really intense, dangerous time, if you are not living at the elite level of society and you are poor, you are hungry, you are going without certain basic needs and not even luxuries, things like bread, then. you can find yourself at the mercy of the bloody code. And it's a pretty brutal time. Which brings us then to the main man himself, the guy who does find himself at the mercy of these things, Jack Shepard, or to give him his full title, Jackarie Shepardson. That's not true. Don't ever call him that. That's not his name. It's Jack Shepard. Let's talk about what we know about his background before he becomes the celebrity that he becomes.

Okay. So it is kind of hard to access the reality of him. because, as you say, he is elevated to this position of being a celebrity and kind of becomes a myth. So a lot of what we know from a young age is very much, you know, like, oh, well, he did this from a young age because we know what happens later kind of thing. But here are the barefax, maybe. He's born in 1702, around about then, in Spittal Field. So again, we're talking about this kind of buzzing, heavily populated, growing, strange, grimy part of London. his father dies when he's young and it drives his family into poverty. So, you know, Jack is someone who is living really on the edge of society.

I mean, kind of on the edge of London right at this time. Like Spitterfields is quite far out. He's very much on the outside looking in in terms of society in terms of the capital city, all of that. He's described in his appearance once he's grown to adulthood as being only five foot four. How tall are you? I'm six foot, exactly. Are you? Me and Jesus.

You and Jesus. Apparently we're the only two, according to my grandfather who's now dead, me and Jesus were the only two people that are exactly six. Coincidence. And you wonder where I got my complex from when I'm compared to Jesus as I grew up. Wow. So five, four, you know, it's not huge.

I mean, short king. And I also think that's where the author of Confessions of a Fox started to put together this idea that potentially. Yes, so not only is he five foot four, but he is described as being slim, very physically fit and very agile and sort of slight. And that's going to come in handy in his career as both a criminal and an escape artist. He's described as being charming, he's confident, he's witty, he's very charismatic. He is apprenticed to a carpenter as a teenager. So good trade here, the potential for a good trade.

So, you know, his father's died, he's been cast into poverty and then he gets this apprenticeship. in terms of an 18th century story, that's a success story for someone in his class. You have secured yourself a skill, a trade. As a young person, as an apprentice, you're living in the carpenter's house. You've got accommodation, an income, or you're being fed, taught, roof over your head, all of that. Doesn't stick with it. Yeah, because else he's not going to end up in prison for being a carpenter's apprentice. Well, look what happened to Jesus.

Dun-da-da-da. Everything comes back to Jesus. I'm not allowed to talk about Jesus on this podcast anymore. Oh, yeah, no, I've seen the comments. Well, apparently I'm the only person to have ever had a baby and need to get over it. We see them, guys. We see them. Oh, God.

Okay, so he is an apprentice. He's not going to stick at it. And he's going to slip into the criminal underworld that isn't really an underworld. It's everywhere. How does he do this? You ask. He spends a lot of time in the pub. That is how you become a criminal, obviously.

specifically the Black Lion just off Drury Lane. What's your favourite historic London pub? Oh, you actually have an answer for this? What is she going to ask me? This is my easy time, Maddie, where you tell all the history and I just sit back and ask some questions. So mine is The Nell on Drury Lane because when I was working in the West End for my 20s and early 30s, we'd always go to the Nell.

Not only is she Jesus, she's been in the West End, darling. And so we'd go to the Nell on a Saturday night. Is that named after Nell Gwent? Yeah. Yeah. And it's just opposite to Dory Lane and the theatre. And we'd drink there and then we'd head out. Do you know what?

It's great because like if you're reading Halley's Covent Garden ladies or you're reading some of these things and you're just like, oh, Covent Garden sounds like such a vibranty thing. I actually have like, okay, it's a very 21st century experience of it. But like a bit of a thing. So we'd go for a drink in the Nell and then we'd go out and spill out onto the streets in Covengarten and then we'd just sit on the clothes. thingy of Drury Lane

theatre and just drink rosé out of a plastic cup and that was my 20s and I wouldn't change it for the world. It was great. I love why you didn't want to answer this question and you've just given it. Oh yeah. Well, no, I didn't know what the question was going to be.

I was like, don't make me think. Okay. But that I have an actual thing of. So imagine Jack Shepherd June the same in Drury Lane, in fact. It is here talking of Covent Garden ladies where he meets a woman

known as Edgeworth Bess. This is a woman called Elizabeth Lyon. Lots of my ancestors were called Lion, actually, or lions. But I don't think they were in England at this time. She's a sex worker, and she's a known criminal. And she's someone who would have been not out of place in Carvind Garden in this moment. There's a healthy sex trade around here, and healthy criminality, and the two are very much kind of interlinked. She seems to befriend Jack, and we don't know the details of their relationship exactly.

At one point, she's described as his wife, which seems unlikely to me, but there's obviously a companionship of some sort or a collaboration going on. But probably as well to bear in mind that this is pre-1753 Hardwick Marriage Act. So the confines or rather the parameters of what constituted a marriage was much looser but still official. So they could have just made an agreement in front of two people and that would mean they were married. So then people leave those marriages all the time.

So, you know, there could be a world in which it's real, but I know what you mean. It feels again like a very. course, so much of this particular history is actually quite, the edges are very blurred. They are, yes. And you know, this is kind of the nature of looking at people in this social class in this particular time period that the records don't exist. And the only reason we often know about these people is because they commit crimes and then appear in the record. And in the case of Jack Shepard specifically, he has been elevated out of that archival record and put on this kind of mythic pedestal. So, you know, he's a character as much as a real kind of historical figure.

So it is hard to get to the reality. We know that Elizabeth does introduce him to, let's say, disreputable people. So she's obviously very well connected, whether that's through her work as a sex worker, whether it's through just the tavern, the Black Lion, that they're spending time and whatever it is. She's introducing people. And he gives up his apprenticeship. And it's around now as well that he comes to know a thief taker, known as the thief taker general. He's like the big boss.

Giving himself that name. Jonathan Wilde. Have you come across him? No, I don't think so. I'm a little bit in my first book. And I really think we should do an episode on him because he is, I mean, he's taking the piss big time. He goes around arresting criminals. He is the biggest, he's like a massive crime boss. He is in on everything and he basically takes out his enemies and his competitors by dobing them in. But he's given himself that title, right? Yeah, yeah. But the authorities are like, yeah, you work for us. And they pay him every time he brings a criminal into them. They're like, thank you very. much for your work, Jonathan Wild. And the relationship between Jack Shepard and Jonathan Wilde starts off potentially as a collaborative one, but it's going to become like the biggest rivalry that London has seen in the criminal underworld. I love that for him. So we have, and this is why we mentioned Queen Anne's start, because most, a lot of that history that you just, in terms of his early life, is taking place during her reign. So now that's very clear. I just jump to conclusions. I'm very sorry. The next thing though is we're going to very much

concentrate in 1724 now where these, his criminality, Jack's criminality really starts to put him in that celebrity status where he gets arrested, he escapes, he gets arrested, he escapes. Give us an overview just to begin with. What is the shape of this part of the story in terms of arrests and escapes because there's a pattern? Okay, so we have five arrests. Five arrests, yeah. And we have a number of escapes. And I'm not going to tell you the number because you might give away the ending. So first arrest. Jack starts his criminality kind of small scale with some petty theft. I don't think we know what he actually stole.

Petty theft would be a really good drag name. Ladies and gentlemen, welcome to the stage. Petty theft. That's good. Yeah, take that if you want it. He's arrested in July 1724 for a theft that takes place at Clare Market, which is a London market. And he's taken to St. Giles Roundhouse, which is one of the kind of smaller prisons of the city. And how long do you think he spends in there, Anthony Delaney?

Now, can I just ask a question before you're asking me to guess again, basically, but I tried not to word it as that, but yes, I am. Can you just, can I ask a little bit more information before I guess? He escapes, I presume, rather than being let out. He's not released. He escapes. Is that true? I don't know. Wait and see. Good God. But then I can't really guess. This is the problem with this, because like, if he escapes, he's probably not in there that long. If he's let out, he's probably in there longer. 12. I'm not even going to say a time period, just 12. Hours, years, days, who knows.

Okay, so he is in prison for petty theft for a grand total of three hours. Okay. During which time, he manages to get up out through the roof and escape. He climbs down the side of the building. Okay, yeah. And I think we're going to come again and again to this. And I think Jack Shepherd's story is so interesting because we think of the London prisons, the big and the small ones.

And at this point, there's huge things like Newgate, but also things like Wellclosed Prison, which was a debtor's prison and St. Giles, you know, kind of smaller operations, which were often, you know, held for people who, you know, have been accused of things in the Bloody Code, but also debtors who were just being held there until they could pay their debts off. And, you know, we think of these as institutions. This is not in the same ways the Victorians have this idea that going to prison is the punishment in and of itself, right? Like 18th century prisons are kind of holding pens, but there is a sense that they represent state power. and control and that once you're in them, you can't leave until you're allowed to leave.

And that the fabric of those buildings is watertight, quite literally, that it holds those people in. And what Jack Shepherd is going to show again and again is that these are buildings like any other. They're vulnerable to all kinds of manipulation, you know, escapology, finding these little, like, literal cracks, little moments of possibility. And it really undermines authority in London as well as the actual buildings themselves. Now, wait, not that I'm not interested in Jack Shepherd because I am because we've designated a whole hour to him or whatever. But if I said to you Jack P. Shepherd, does that mean anything to you? Is he someone from the First World War?

No. He's an actor on Coronation Street. And he plays David Platt on Coronation Street. But imagine being Jack Shepherd and then Jack Pea shepherd. Isn't he quite slight as well? He is. Oh my God, petition for him to play Jack Shepherd. Jack P. Shepherd as other Jack Shepherd without the P. Casting sorted.

Yep, thank you. Sorry. Now, so that was the... Thank you for that incredible... No, listen. I don't think you would have been happy today without... I would have thought of that when I got home and thought, I can't believe we didn't mention that. Yeah.

Okay. Right. So he's escaped. No, he's been arrested once, escaped after three hours. You know, so this is certainly unusual that someone has escaped. But, you know, this is a small prison. It's not that much of a big deal necessarily. He's not been arrested for anything enormous. He draws attention to himself by this. The whispers start, the stories start to circulate. But, you know, one three-hour stint in prison and an escape through the roof doth not a celebrity criminal make. Manny's the time I've said that. So well no faith.

Okay, so he needs to be arrested again, doesn't he? And he is going to be. So later on that year, so we're in July 1724. He's arrested this time with Elizabeth Lyon from the Black Lion pub. Which isn't even that unusual that often couples would be taken up for certain things or if sex worker and a cull or whatever. So, you know, people are arrested together. And often watchmen or thief takers, you know, someone's up to no good. And then the woman they're with is like, hey, leave him alone. They're like, right, you're coming to. You know, there's not a lot of specificity here. The offence this time is supposedly pickpocketing in Leicester Fields, which is now Leicester Square, isn't it? It's the area around there, which is probably still very pickpockety. Well done. This time he's taken to new prison in Clark and Wales. So we're kind of like escalating up the chain, I suppose, of prisons.

Give him a better holding cell this time. Well, he's not famous enough at this point for them to even think of that. Oh, yeah, of course. So Jack and Elizabeth are put into the same cell. Um, they're going to escape again, obviously, this time. So he's gone out of the roof. Yeah. Before thoughts on how I might escape this time.

I'm going to make you guess so much on this episode. What would you do if you were, okay, if you were stuck in this room, what objects are you going to use to escape? I'm not going to try. You're not going to try. Thank you. I love the way you didn't fight me on that. I know. Yeah.

Yeah. No, you're not. You're not. Okay. But for the sake of the thing. For the sake of the thing being the podcast, we are employed to do. do. How does he escape?

Diggs down. If he went up the first time, he's going, Oh, okay. No, you're like, oh, no. Okay, correct. I mean, sure, but he's, no, so he's several floors up, so not an option. Okay, so what he does do is he and Elizabeth take the bed sheets off the bed in the prison cell. They tie them together and they go out the window.

I have an image here that I would like to. That's why I've got a picture of somebody letting somebody out the window with a bed sheet. Fine. was in front of you the entire time. Describe the picture, please. Okay, it looks, I would say if I were to, oh, there's the clue it is later. I was going to say, if I had to guess this is later than the 1720s, because she is very romanticised. She's got very polite little, I love her. This is Elizabeth, is that her name? Yeah, Elizabeth's line. She's, she's being let down on those bed sheets. She's got very polite, dainty little ankles and you can just about see her ankles underneath her, her shifts.

And she's a sex worker. Let's not forget. She has to be sexualised in this image. Although the clothes that she's wearing are not 1720s clothes. They are far more later century clothing. But she's very romantically being let down. She's being let down on like kind of spiky things. Anti-pigeon things. Yeah, looks like that.

He's up in his little half window and he's looking very gnarled face, I must say, where she's quite beautiful. Well, to be fair, he is having to lower the entire body to a woman out of like, oh, who. No, darling, you don't wear anything. It's fine. And he's letting her down and yeah, he's up there. Now, in the background you can see, like, actually, it's very bucolic. It's not very Londony at all.

Or is my eyesight just really bad? No, I see trees and hills. And then obviously there's a prison that they're being, there's a big wall around the prison. And then it's signed George Crockshank. So this is how I do know that it is later than the 1720s. So this image is from a novel about Jack Shepherd by William Harrison, Ainswerell. Who, have you ever come across him? I'm obsessed with him.

So I have a first edition of this novel, the Jack Shepherd novel. Do you actually? I do. Yeah. So I bought it when I wrote my first book because, so Ainsworth is writing in the first half of the 19th century, looking back at the 18th.

And he writes a lot about the French Revolution, the Gordon riots. I think he wrote about, he writes this novel about Judge Shepherd. He's sort of obsessed with like a generation or two before, which is really interesting. And I'm always interested in people's perspective on the 18th century as I get sort of further away from it.

So he's very much just sort of an early Victorian writer. And George Crookshank worked with him across all of his novels and did these illustrations. And the reason why I bought this first edition was because in the Jack Shepherd novel, we know he's going to become a criminal because in the early illustrations of him, there is graffiti everywhere in the background. And for anyone who hasn't read my first book, you know, it's all about graffiti in the 18th century and this idea that it was associated early on with criminality. And Jack Shepherd, we even see him carving his own name when he's a,

an apprentice into a bit of wood. So I bought it for the images really, but it's a stonking good read. Stonking. It's stonking. It's sort of ridiculous, you know, but it's worthy of Jack Shepard, the myth, not the man, necessarily. But, you know, again, we see in this image that we're talking about, this kind of, as you say, romanticisation, this idea that Shepard is this sort of unstoppable force and that he's

just on this journey of ridiculous exploits. escaping constantly and that he sort of can't be, he can't be stopped and, you know, he's bringing people along for the ride. That's the second arrest and the second escape. We are about to go to break and when we come back, he's going to get arrested again. Right. We're back. Third arrest.

And we have, oh, this is where Jonathan Wilde, not Jonathan Swift. And that is what's in my head every time I talk about this because he's the only 18th century Jonathan that I know about it. We should do an episode on Jonathan Swift at some point, but. The Lilliputians. Jonathan Wilde, the thief-taker general, one time... He's entering the chat. One-time lad that he hangs around with is going to get involved.

They're not going to be friends anymore. Okay, so Jonathan Wilde, yep, thief-taker general, as he's known. He's a criminal of all kinds. He's known as a poacher, but he's also a gamekeeper. How does that work? He's sort of this contradiction of things. He's like, he's in with the people in authority, but he's also governing the underworld as well. He, as I say, he brings people in, he's paid for it crucially.

If you're a criminal in 18th century London, you are under the control of Wilde. And Jack simply refuses. He's like, no, no, I'm a lone wolf. I'm doing my own crime over here, my own escapes. I can't be stopped, won't be stopped. You're not the boss of me. Wilde doesn't take this well. Can I just say, I like both of those aspects.

Like, obviously, I don't want to be a criminal. But if you're going to be a criminal, you might as well be the king of the criminals. Oh, you'd be the thief-taker general, would you? No, I don't think I would because it wouldn't have the energy. But I think I'd probably be Jack Shepherd where I'm like, well, I'm just not going to do that. It's more likely, right, that I'm going to just do that over there rather than do the group thing. Yes. Yeah, you're not doing the group thing.

In August 1724, we're still in 1724. Wilde decides he's going to get rid of Jack because Jack, you know, he's starting to be a bit famous. And Jonathan Wilde is the only famous criminal. He doesn't like some notoriety that this new celebrity criminal has got. So he dobs him in for burglary this time. He says that Jack robbed the home of his former carpenter master, a man called William Kneebone, which is called Kneebone. Kneebone.

I know, great name. Jack is captured. He is brought before a magistrate and he's sentenced to death. So it's not looking great. So he's had two L incarcerations. Now is going to be incarcerated again because that's the thing you're held. Even if you are going to be executed, you're going to be held until the next execution day. Yeah.

So he's taken to Newgate this time. Okay. We're at the pinnacle now. Yeah. So Newgate kind of not far from where he started in Spitterfield's right. It's where the old Bailey stands now. It was built in 1188 and it stood until 1904. It is notorious.

The conditions in this prison are grim. Prison fever, which is probably typhus, you know, is just a constant. Like, you might go in under a conviction for a crime that means you're going to be hanged, but you might not even make it to your execution day. Like, it's not good in there. It's really, really grim. It's overcrowded. It's squalid. It's kind of, I always imagine it is this like incredibly dark, dank space inside of these really thick walls. And it had very famously these really heavy prison doors. And because it doesn't stand anymore, we can't go and experience this space. But the Museum of London or the London Museum is it's about to come if it ever reopens. I think it's meant to be reopening this year. Has at least one of the doors from the prison.

If you ever been to see it. And it's so, you get such a sense of like the imposing nature of this structure. Yeah, no, it is. And it's, you're so right about Nuget because it's disappeared architecturally. we do, I think, underestimate what that experience might have been like in the 18th century. I think it's, we don't consider it enough as, you know, it's a real sort of spectre of an old form of London. And it's, you know, it's there and it's really great moments. It's damaged during the Great Fire of London, 1666.

In 1780, it's burnt to the ground again during the Gordon riots. Again, I mentioned in my first book. I'm really plugging myself today. You are here? Yeah, wow. It's just, I'm covering so much of the same terrain. Yeah, yeah. It's closed in 1902 and it is around that time over the next few years it becomes replaced by the old Bailey, which again is kind of such a sort of huge institutional column of British authority now.

So Jack finds himself in Newgate. He's waiting to die. Things aren't looking good. This is a fortress. I can think of, listen, there probably is, but off the top of my head I can't think of anybody else that comes to mind that has escaped Newgate. I mean, do you want to commit to that? No, I said, there probably is, but you'll let us know in the comments we know. It must have been near impossible.

But it's not impossible. Yeah, well, it's not. Yeah, yeah, yeah, yeah. Okay, so for this one, he's going to need a bit of help. And one of the things about Newgate is that you can have visitors and often people would pay to come and see famous celebrities. We did one of the OG, in fact, I think the first ever after dark episode on Sarah Malcolm, A murderer in, I think that's the 1720s as well, isn't it? Around the same time.

And she is taken to Newgate, and she is painted by William Hogarth. People pay to come and see her. She's so notorious. You know, there's a sort of coming and going of people constantly, and you would have visitors. People you knew, but also total strangers as a prisoner. And one of the visitors to Jack is Elizabeth. She comes in to see him. What does she bring?

Well, the jailers don't think to search her. So she smuggles in a metal file. Now, the newspapers at the time report this escape. And I take this with a pinch of salt, essentially. They say that the jailers themselves are sat in another room somewhere in the prison, sitting around the table all discussing Jack's previous exploits and his escapes. Meanwhile, he's busy filing away. Yeah, like, oh, what was that?

Yep, keep going. he manages to make a little bit of a gap in a door and because he's so slight he gets through it he is off out into the world he's gone so it's not like he breaks well he breaks the door but like it's not like in the other ones he gets he kind of breaks the boundaries

with this one okay the door is a boundary but like he's still in turn he's still inside the prison and has to then navigate the kind of public areas with Elizabeth. Yeah. I mean, it's, I suppose again

because like coming and going in the prison. Yeah, exactly. It's a world in which, you know, he's just disguised he escapes. He makes this way out. Nobody notices.

It's not great in terms of, if you're a prison guard, you're giving me in big trouble. This is a famous criminal who's waiting to die. Obviously, Jonathan Wilde, the thief chaker general, not happy when he hears this.

Pretty annoyed. He's feeling pretty humiliated. This is three. We're on three now. The media at this point, they're biting, they're interested. So, you know, they've been following his escapes really from the first, but this is like, this is escalated now.

He's now a household name. Biographies of him start to appear already. You know, he's still alive and out there in the world. Ballads are sung about him, the cheap broadsides, you know, that you would get kind of pinned to the wall or Solon Street Corners, all telling tales of him. And he's like, what, 22 at this point? He's not even 22, I think. Maybe he's just 22.

Yeah, yeah. In his early 20s, yeah, definitely. Exactly. And he, you know, he's becoming, I suppose, what we might describe as the sort of one of the first mass media celebrities. He is everywhere. Everyone knows something about him, whether it's true or not, of course, is debatable. The Daily Journal publishes a letter supposedly, again, not Pinch of Salt, written from Jack, who's just escaped Newgate to the hangman who didn't get an opportunity to hang him. do you want to read this? And I will just caveat this by saying that he signs it John Shepard.

So we are talking about Jack Shepard here, but he signs at John Shepard. And confusingly, he refers to the hangman as Jack. Just to hold on your mind. Let's keep that nice and clear, yeah. Okay. Sir, I thank you for the favour you intended me this day. I'm gone a few days for the air, but designed speedily to embark. And this night I am going upon a mission for a supply.

It's a stout fortification. But what difficulties can't I encounter when, dear Jack, you find that bars and chains are but trifling obstacles in the way of your friend and servant, John Shepard, from my residence in Terra, Australia's incognito. Okay, he didn't write that. No, he absolutely didn't write that. Oh, there's more. He's absolutely taunting the hangman, basically saying, like, I'm off in a little holiday. I've gone for some fresh air because Newgate was not to my take. And, you know, the shackles can't hold me down.

Yeah, and then he does a PS, which I think is just, I mean, obviously he didn't really write this. But like, this is petty. He says, pray my service to Mr. Ordinary, i.e. the chaplain of Newgate prison, yes. And Mr. Appleby, the publisher of criminal biographies. Okay. So he's basically like, say hi to my friends. Who would have gained money, both of those people from his death, had he, and a lot of money because he was famous. I suppose what this letter shows, even though it's very likely not written by Jack Shepherd.

who, you know, possibly couldn't even write, actually, like his literacy level. I mean, maybe if he was an apprentice, but I'm not convinced he would have written this. But I suppose what it shows is this kind of interesting relationship that is building between the idea of Jack and the media. And, you know, we see this again with another famous Jack in the 1880s, right? This idea of Jack the Ripper, supposedly writing into the newspapers, obviously committing far more serious and grim crimes. But this idea of sort of the sort of mutual reliance, I suppose, the codependency of a celebrity criminal and the media who builds them up.

And we're already in the 1720s seeing that explored. So in reality, Jack has escaped. We know that is fact. He has gone from Newgate. And he's, you know, becoming this kind of cult hero. But in reality, he is still a wanted man. There's still a death sentence hanging over him. he's recaptured.

Already. Yeah. Quite quickly. Quite quickly. Because he's pissed Jonathan Wilde off so much, Wilde is now obsessed with taking him to the gallows. That's like his mission in life now. He's like, I need to go out of this guy. And where are we now?

That was three, we're at four. We're at four now. Okay, yeah. We're at four. He is dragged back to Newgate. And he's put in Newgate's most secure room, which is known as the cast. And just to give you an idea of how serious they are about keeping him there, he's handcuffed and there is a padlock used on the handcuffs to attach him via an iron staple to the stone floor.

So his hands are tied to the floor, essentially. He's not going anywhere. Yeah. Or is he? While he's in prison and you gate this time, people are now paying to come and see him. People are turning up every day to come and have a look at him. so much like Sarah Malcolm artists are coming in to sketch him

that interest is is sort of building all the time and also he starts when he's not handcuffed to the floor he starts to dress in fine clothing he's presumably somehow making money out of this or people are bringing him clothing as gifts right

and so he's really kind of putting on a bit of a show I suppose he's trying to get people on side if you're there waiting to die maybe you're hoping someone's going to bring you something to help you escape. Maybe you're just hoping to get the public opinion might save you if you're lucky enough. And so he really kind of leans into this idea of being a celebrity criminal,

right? He's sort of holding court at Newgate. So he has this celebrity status. He is now shackled and manacled and really kept in place in prison there, not wanting him to escape. But he has known for his escape attempts. And I'm assuming there is another one in the pipeline, but maybe I'm wrong. There is. He escapes again. This is the, what are we on now? This is the third.

No, fourth escape. I've lost count. Yeah, no, I'm... Anyway, so, but, okay, so he's arrested in September. He's in Newgate. On, in October, on the 14th of October, he has an opportunity. And I don't think this is a coincidence, right?

There's no evidence that he was involved in organizing this. But what happens is Jonathan Wilde, thief-taker general, is at the old Bailey, which is next door to Newgate, right? And now the current building takes up the sort of footprint of part of Newgate. He is standing there, the old Bailey, when he has it, someone comes up to him and cuts his throat. Wild. Yeah.

And obviously this draws a crowd. There's enormous sort of moment going on. Interesting, Wild survives this, which is pretty incredible. And I think gives you a sense of the kind of man that he was that he had his throat cut. and lived. But during this confusion, the uproar that happens, inside Newgate, Shepard's like, this is my moment. Now, this is, I just, he's, not only is he like an incredibly sort of, you know,

slight person who can move through all these spaces, he must have been incredibly determined and strong, because what he does to get out is, when they go into his cell, the floor is covered in rubble, he's gone through the ceiling again, which remember he did in his first escape. He's then broken through what I call the six great doors. of Newgate. These are locked and bolted. And when the jailers come to find that he's gone, the locks and the bolts are just strewn all over the floor. So he's removed them all. I mean, determined. But also, he got through six of those and nobody noticed him just sort of wheedling away

working on these doors. He then manages to get to the roof and he uses his blankets from the prison cell to climb down onto the roof of a shop next door, climbs off that roof, into the street and walks away. Susan, I'm suspicious. You don't buy it. I don't buy that. Like, we know Newgate better than that. Like, also blankets even, like, go to that.

Most people don't have blankets in Newgate. So I think there's someone helping him on the inside, maybe benefiting from, you know, the constant cat and mouse of him coming in out of prison, the money that's changing hands with visitors coming to see him, who, you know, maybe are paying for his extra blankets, etc. Yeah, because you could. You could do that. By people favours in prison, you know, nicer food, wine, beer, etc. And we know he's been probably bought nice clothing. So maybe he just, you know, maybe someone's bought the blankets for him. But they've clearly also brought in tools for him to dismantle these six doors.

So I don't think anyone's looking away for long enough for that to happen. He's being helped. So he's gone again from Newgate and he's literally just stepped into the street and disappeared into the London crowds. It's a magic trick. Okay. Well, my suspicious hackles are up. Is that a word, hackle? Yeah, like on a dog when the back of the fur, on the back of the next end up.

But when we come back, we are going, well, Maddie is going to tell us where it all goes wrong for Jack Shepherd. Maddie, where does it all go wrong for Jack Shepherd? What an astute and interesting question. It does go wrong, unfortunately. Well, fortunately, unfortunately, I don't know. It depends on your perspective. I'm sort of rooting for him. I've brought into the sort of heroic.

Yeah, go on. Yeah, mythology. Yeah. So he's arrested for what will prove to be the final time, spoiler, on the 1st of November 1724. I mean, this is quite the career over this year. You know, he's been arrested and escaped. This is crazy. This is still the same year.

He's found hiding in lodgings on Drury Lane, which, of course, is, you know, where he initially meets Elizabeth at the pub and all of that. So this is very much his old stomping ground. Stupid mistake, like rookie error. Jonathan Wilde's after him again. It's Jonathan Wilde, you know, holding his throat together as he marches around London. Zing through his fingers. I mean, he's sort of like, you know, a great, one of those villains in like an action movie that won't die. And the hero keeps bashing them down.

They just keep going back up. You know, it's pretty awful. He's arrested again. He's taken to Newgate. He's put in irons again. And he is now kept under close guard. There's no looking away from this now. Like, people are watching him 24-7.

So this is the fifth the rest. So he's taken to Westminster Hall to plead in front of the Attorney General. And, you know, I think this says. so much about how famous he is that he's allowed to come before the Attorney General and kind of beg for his life and say, no, please, the public love me. I can't die. And the Attorney General says to him, you keep escaping and you could potentially just go and anonymously have a new life. Why do you keep committing crimes? And coming back to Drury Lay. And coming back to like, mate, you've had your chances. Go to Kent.

Yeah, go to Kent. That's the most exotic. Quiro plays Anthony can think of work. So he's not allowed to escape again. He's not allowed to be let off. The Attorney General has no sympathy. And so execution day comes. And as per tradition of execution days, there are crowds in their thousands outside of Newgate,

particularly because this is Jack Shepherd's day of death. People, you know, sort of vying to get a glimpse of him. They're climbing trees. They're climbing into buildings, looking out of second and third story windows, climbing on horseback on each other's shoulders. They really want to get a glimpse of him. It's estimated that between 100 and 200,000 people go to Tyburn within.

200,000. You sometimes hear of 100,000, but 200,000 is... Particularly in London in this period at the beginning of the 18th century. We're only in 1720s. This is really significant. Almost everyone. But on the day of the execution, there is a plan for him to escape. You know, Elizabeth and the rest of his cronies are not going to let this go.

And so his friends and supporters do hatch a plan that they're going to smuggle him tools, once again, to escape before he's taken to Tyburn. And potentially on the way on that journey as well. Sure, to grab them. The criminals will be put on the cart and paraded. And there's a sense that maybe they can pass him things and he can loosen his hands or whatever and then leap to his freedom. And there's a sense as well that there's some sort of discussion about maybe overpowering some of the guards and just dragging him into the... into the crowd. But the prison guards get wind of this. And to be honest, you'd be primed for this. You'd be like something's going to happen. He's transported under extra protection. They can't

get anywhere near him. And his final escape plan fails. He is sent to the gallows. And I can imagine the atmosphere that day. And if you're a ballad singer or a food vendor or anyone who is involved in the economy of execution day, you are making. a killing this day. This is a huge moment. You're welcome. I would imagine that what we, the reason that this story then endures after death, which I would imagine only becomes more popular. I mean, you can fill me in on this. Yes. Is because he becomes a sort of, I would imagine, folk hero type thing going, look at this underdog who's trying to push back against the establishment. Right. Yeah. And he's got his own

community and he's got the everyday man thing going on. Is that kind of where that goes then? I think that's very fair. Yeah. I mean, I think there's a sense of, I think we have to split the two Jacks in this moment, right? We have Jack, age 22, who goes to his death. And the Daily Journal reports on the execution day, it says he vehemently resisted and endeavored to beat the officers. This is a man who doesn't want to die. He's 22 years old. He is struggling to the last. He does not want to face that noose.

But we have Jack the myth, the legend, who, as you say, kind of becomes this almost Robin Hood figure, right? There's this, the story that is told of him is not that he's committing petty crimes and hangs around in these kind of dodgy taverns with sex workers and, you know, as part of this kind of underclass. But, you know, that he's somehow,

that it's politicised, that he's stealing from the rich. So is he really to blame? why is that that bad? You know, and we see him kind of pass into into folklore and into all these kind of different cultural retelling. So he appears in poems, in broadsides, as we said. Daniel Defoe, talking of other 18th century writers, potentially is attributed to Daniel DeFoe, writes a biography of him.

The Beggar's Opera, which appears only in 1728, so not that long afterwards, is all about Jack Shepherd, which I didn't actually realize. Oh, I don't know if I put two and two together there. Yeah, so that's kind of interesting. You know, and I think it's fair to say that he's one of the sort of first, yeah, mass media celebrities. I don't know if I'd say he is the first, but I think he's one of the earliest. And certainly the media is kind of cutting its teeth on how to report these stories and how to

tell these tales in ways that whips up such public feeling that you are selling copy after copy after copy. You know, this is big business. As we've already said, in 1839, William Harrison Ainsworth writes his novel, illustrials. by George Crookshank. And that becomes a Victorian bestseller throughout the 19th century. And Ainsworth actually has that novel adaptive for the stage as well. So Jack Shepherd is really living large across all these different kinds of media. And he's a subject of TV shows now, of plays.

As you've mentioned, at the beginning of novels as well, even today, you know, that he kind of is reinterpreted. And I love that interpretation of him maybe as a trans man. And I think, you know, it kind of speaks so interestingly to the physicality maybe of that character and the sort of the ambiguity as well and that we can't really access the real person. So why not, you know, sort of riff on that a little bit. And that's it for me. You've some of my feelings on that up going. I actually think we're really far from the history on this sometimes.

And therefore, why not? Yeah. You know what I mean? Like there's so much invention happening even in several. 1724, that you might as well keep inventing. That's what this story is. Now, can I just ask you, before we go, give your interest in this history a mark out of 10. How interested are you? I was going to do this as a start of the episode, but it would have been very rude, so I didn't. I think this is fascinating because I think it gives such a sense of, I know I'm not giving a mark of 10, I'm getting to it. It gives such a sense of the sort of the bubbling, busy, complex, layered world of early. George and London that I love and that I've spent so much time researching and writing about. In terms of Jack Shepherd himself, I think there is a slight frustration then because, as you say, it's the distance and so we can't quite access who he was. But I think as a sort of structured

story, and I see it very much as a story, these multiple escapes and the sort of cat and mouse story between him and Jonathan Wilde, I think is so fascinating. So I can say a 7.5 out of term. Three. I'm so glad that's done. He is the least interesting 18th century person in the entire world. No, but I'm glad that you did it. I'm glad we did it. Come back. You have to finish the show.

You have to finish the show. I do you? I don't know. It's just the distance between the history and the myth. That's what it is for me. You know I can struggle with that sometimes. And when I saw this on the schedule for this month, I was like, oh, Jesus, not Jack Shepard, please.

No, but I'm really glad. we did it because it is a staple 18th century. Like, we have to do this. And there's so much proper thing in it. And that's why I did like Confessions of the Fox because it was like a twist on it. Make it up and make it something new and all that kind of thing. Okay, so what we've learned is this was a waste of time.

No, it wasn't. And that's why I didn't say this at the start. Leave your rating our 10 in the comments below. No, don't. I did. I did truly enjoy the conversation. I don't think there's any coming back from there. No, there is.

But as a subject matter, I was just a bit like, and you didn't think of this you just delivered it with very professional acumen but it's like it yeah I don't know it's never one that appeals to me

I think this is over now what the whole podcast Bye Goodbye