Jack Sheppard: Housebreaker & Escape Artist Extraordinaire

Sheppard was a thief, a romantic hero, a highwayman of the urban proletariat, a Houdini whom no prison could hold.

ImageOn November 16th, 1724, after four successful escapes from prison, Jack Sheppard was captured for the last time and hanged at the gallows at Tyburn for his crimes of theft. Despite being only twenty-two years of age at the time of his execution and an active criminal for less than two years, he became a notorious figure across the classes for his cunning abilities as an escape artist.

To understand Sheppard’s case fully we need to start at the beginning.

Jack Sheppard was born in 1702 into the lower working class; his father was a carpenter as his grandfather was before him. While Sheppard and his only surviving sibling, Thomas, were still young their father died, leaving their mother to raise them. He spent two years at a school at Bishopsgate Street before beginning his apprenticeship as a carpenter.

His career as a carpenter seemed promising, but before he had completed his six-year apprenticeship, he fell into the company of “abandoned women” in his frequenting of the tavern, Black Lion. One of the most prominent women in his acquaintance was Elizabeth Lyon or “Edgworth Bess” as she was known. And this became the beginning of Jack Sheppard’s criminal career.

Taking advantage of his work as a carpenter, Sheppard frequently robbed the houses he was working on and brought his newly acquired possessions to Edgworth Bess. He decided to make a career out of housebreaking when he realized his success in the act.

The Arrests & Subsequent Escapes:

1. Tom Sheppard was also a carpenter and a thief, and in August of 1773 “he was indicted at the Old Bailey for two petty offences, and being convicted was burned in the hand.” He sought out his brother after his discharge to borrow forty shillings and for Jack to take him on as a partner in crime. Jack agreed and the brothers set out with Edgworth Bess and robbed the shop of linen-draper, Mrs. Cook, as well as the home of Mr. Phillips. Tom was caught and brought into custody when he went to sell some of the stolen goods to Mrs. Cook. In hopes to save himself he offered up the names of his brother and Edgworth Bess, but the two were not found.

A companion of Jack Sheppard’s, James Sykes or “Hell and Fury” betrayed his friend by calling a constable in hopes of receiving a reward upon his conviction. Sheppard was taken into custody, sent before the magistrate, and, upon his orders, was taken to St. Giles Roundhouse. But during the night he broke through the timber roof of the building and made his first escape.

2. Sheppard’s second arrest came on May 19th 1774, when he was crossing Leicester Fields with an acquaintance named Benson. Benson attempted to pickpocket a man out of his watch, but failed and the man cried out, “A pickpocket!” Sheppard was caught and spent the night at St. Ann’s Roadhouse, and was visited by Edgworth Bess who was then taken into custody “on suspicion of being one of his accomplices.” The next day they were seen before a magistrate, charged with felonies and sent to New Prison. They were believed to be husband and wife, and therefore were permitted to lodge together in the room known as Newgate Ward. Within a few days of his stay at New Prison, Sheppard launched his escape. After procuring the required instruments for his escapes from a number of visitors, “he filed off his fetters and, having made a hole in the wall, he took an iron bar and a wooden one out of the window; but as the height from which he was to descend was twenty-five feet he tied a blanket and sheet together, and, making one of them fast to a bar in the window.” The two descended down the rope of blankets, and then proceeded to climb over the twenty-two foot surrounding wall by using the locks and bolts of the gate to pull themselves over it.

3. Joseph “Blueskin” Blake was another notorious thief of the 18th Century who was executed just days before Sheppard’s execution. “Blueskin” became the associate of Jack Sheppard and in their time together they committed countless bold robberies. The two men sometimes entrusted their ill-gotten gains to William Field who promised to find a buyer for their goods. Field betrayed Sheppard and “Blueskin” by stealing their goods and turning information of the two thieves over to Jonathan Wild. Sheppard had made an enemy of Wild when he refused to work with him, and when he heard of Sheppard’s latest robberies he turned him and his accomplice in, which led to their arrest. Wild was otherwise called “Thief-Taker General,” and he was known for playing both sides of the law; he was seen as both a crime fighter and a prominent gang leader.

“On Monday, the 30th of August, 1724, a warrant was sent to Newgate for the execution of Sheppard.”

On the evening of the warrant, two ladies went to Newgate to visit Sheppard. Before their arrival, he had cut into one of the spikes that separated himself from visitors in order to weaken it. When the women arrived he broke the spike free, pulled through the opening and the women helped him down. It is said that some of the guards had been drinking on this night, allowing Sheppard to easily make his escape.

4. By his fourth arrest Jack Sheppard was a household name and he was considered a working class hero.

After his last escape he met up with a friend known only by Page. The men decided to travel to Northamptonshire to visit with Page’s family, but returned to London in under a week. Sheppard, after they returned, spotted a watchmaker’s shop attended by only a boy. He took advantage and made away with three watches. Friends informed Sheppard that serious efforts were being made to bring him back into custody, so it was decided that they would go to Finchley to wait until the efforts of the search died down. But information of Sheppard’s whereabouts reached the “jail-keepers” and he was brought into custody again.

Having been fooled so many times before by Jack Sheppard, strict steps were taken to prevent another escape. “He was put into a strong-room called the ‘Castle,’ (…) loaded with a heavy pair of irons, and chained to a staple fixed in the floor.” This did not deter the great Jack Sheppard. From the statement of Sheppard himself, it is known that visitors were watched allowing him no assistance, but he spied a nail on the floor of his room. He got himself out of his chains, but was unable to flee his cell. When he was found, he was also given handcuffs.

Sheppard attempted a second time to escape his sinister fate. First he released himself from his handcuffs and shackles, and then proceeded to create a hole in the chimney, which led him to the Red Room that had long been abandoned. About the room Sheppard said: “the door had not been unlocked for seven years; but I intended not to be seven years in opening it.” Not long after he opened the door, and made his way into the chapel. He then made his way through a series of rooms and hallways and made his final escape over the wall with the whole escape taking him approximately five hours. Image

Final Capture & Execution:

The fate of Jack Sheppard was secured in his fifth and final arrest due to his decision to indulge himself in the hard stuff. He spent the early evening drinking with his mother, and left her to drink about the neighbourhood visiting with many friends and acquaintances. His companions attempted to warn him about his inebriated state, but he ended the night by being taken into custody and was unable to resist.

He was visited by a countless number of people from all ranks of society during his final days. Sheppard told the visitors stories of his robberies and escapes, and pled with noblemen to intercede. He also frequented the chapel during his time before execution. “Having been already convicted, he was carried to the bar of the Court of King’s Bench on the 10th of November, and the record of the conviction being read, and an affidavit being made that he was the same John Sheppard mentioned in the record, sentence of death was passed upon him by Mr. Justice Powis, and a rule of court was made for his execution on the Monday following.”

Although his fate lay before him, Sheppard did not yet give up. He brought with him a penknife in an attempt to cut away the ropes that held his arms and flee into the crowd, but an officer found it in his pocket (he also cut himself in the process).

Sheppard also asked that his friends place him in a warm bed after his execution and to open a vein. He had been told that this act would revive him.

The attending crowd was sorrowful as Jack Sheppard accepted his fate with decency. It is said that he died with great difficulty. His body was given to his companions and taken to Long Acre to a public-house, and he was later buried in the cemetery of St. Martin’s-in-the-Fields.

This is an excerpt from the sermon following his death:

“Oh, that ye were all like Jack Sheppard! — Mistake me not, my brethren, I don’t mean in a carnal but in a spiritual sense, for I mean to spiritualize these things. — What a shame it would be if we should not think it worth our while to take as much pains and employ as many deep thoughts to save our souls, as he has done to preserve his body.”


Final Thoughts:

Jack Sheppard can be said to be the real life version of Robin Hood (although there is speculation that Robin Hood was initially based off of a real man); both were outlaws known for their clever and cunning ways, but, despite their criminal behaviour, they both became known as heroes among the lower class. The two men also dealt with corrupt lawmen in Jonathan Wild and the Sheriff of Nottingham respectively. While Robin Hood is regarded as a philanthropist, stealing from the rich to give to the poor, this is a relatively recent adaptation that was used to appeal to young children.

Despite Sheppard’s criminal behaviour, he remained non-violent throughout his life. He also reached out a hand to his fellow companions (although his help was illegal). During his first robbery with his brother he allowed Tom to keep all of their goods. He also never turned in any of his companions or sought revenge on those that betrayed him.

Jack Sheppard was educated, and he was also viewed as witty and handsome, and became a hero among many. He was immortalized in a number of plays, poems and books after his death, and he was even mentioned in Bram Stoker’s Dracula:

“He is safe now, at any rate. Jack Sheppard himself couldn’t get free from the strait waistcoat that keeps him restrained, and he’s chained to the wall in the padded room.”

So what does Jack Sheppard’s account say about the 18th Century? First, theft was treated a lot differently than it is today. I can hardly imagine someone receiving the death penalty for Sheppard’s crimes. We do not even have the death penalty in Canada. Second, I think that Sheppard’s case says more about us than it does about him. Why was he so popular, why did masses of people celebrate him and his exploits?

I think it is because of his social status. Jack Sheppard was a man of the working class, and in his robberies and escapes he was seen as rebelling against authority as well as the social structures of his time. We can still see this idea today. Think of Bonnie and Clyde who are still celebrated in books, songs, and movies. While many would view the murders they were responsible for as wrong, people are more forgiving about the bank robberies. Maybe this is partly due to the way society feels about banks. Especially in light of recent events in America, the working class views the banks as “robbers.”

The gap between the rich and poor is constantly growing, especially with the vanishing of the middle class. While class structure now seems different than in the 18th century, we do not speak in terms of noblemen and aristocracy, but the vast divide remains – and may be seen to be all the more frivolous today. Think of Beyonce reportedly buying her toddler an $80,000 diamond-encrusted doll, while a woman down the street is unable to provide basic nutritional requirements for her own children. How does this make you feel?

People are working three jobs, looking to food banks for support, and are still straddling the poverty line. And for those of us at the bottom of the economic ladder it seems we’ve also got the most hands in our pockets. People are responding to this gap – think of movements like Occupy Wall Street. Peaceful protest is often quickly shut down, and usually by force. People are not being heard, and situations hardly seem any better than in Sheppard’s day. Think of the wildly popular series, Breaking Bad; a show about a working class man who learns he has lung cancer. He then turns to a life of crime to ensure his family is financially secure after his death. Walter White is tattooed on arms, and displayed on t-shirts for the same reasons that Jack Sheppard has been written about in plays and novels: they both stick up a middle finger to authority and refuse to accept the hand that’s been dealt to them.

Charles MacKay had this to say about the notoriety of thieves in his book, Memoirs of Extraordinary Popular Delusions and the Madness of Crowds:

“Whether it be that the multitude, feeling the pangs of poverty, sympathise with the daring and ingenious depredators who take away the rich man’s superfluity, or whether it be the interest that mankind in general feel for the records of perilous adventure, it is certain that the populace of all countries look with admiration upon great and successful thieves.” 

What are your thoughts on Jack Sheppard and his case?

Sources and further study of Jack Sheppard:




And a song that reminded me of Sheppard: https://www.youtube.com/watch?v=KOQ4pkUAFbA


2 comments on “Jack Sheppard: Housebreaker & Escape Artist Extraordinaire

  1. Hi Sierra,

    There are a few things that I think you did really well and one thing that could use improvement. I found that you did a very good job with the summary portion of your blog post. I especially liked the comparison between Jack Sheppard and Bonnie and Clyde and the song which reminded you of Jack Sheppard. It was clear and gave the reader a good understanding of Jack Sheppard’s background and criminal activity. It sets up the post well for the analysis of what the trial tells about 18th century Britain. I think that the area of your post that might need a little bit more work is your analysis. Your analysis is very short compared to the summary portion of your blog post so you could improve by making the summary section longer/more in depth. Since this part of the momento mori post is so important it will really add to your overall post.

  2. ashinnan says:


    I tend to agree with Jessica, in regard to the suggestions she made that could benefit your post. The summary you provided us with was extremely helpful and painted a clear picture of the trial, and didn’t leave us with many questions, if any, about how the crime and trial unfolded. With such a clear depiction of the trial, it might be nice to have a more detailed account of what you think the trial tells us about the 18th century. Perhaps some examples of how social status effects people today, besides just the Bonnie and Clyde reference, because comparison is a helpful tool in understanding a society we were not a part of.

    Other than needing a little more analysis about what the trial tells us about the 18th century, I think you did a great job with editing your post. There are very few grammatical mistakes that I can find, and it is clear that you spent a lot of time with this post!

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