"Honest" Jack Sheppard

Podcast Transcript

In early 18th-century London, a petty criminal became one of the most celebrated people in England.

He wasn’t celebrated despite the fact that he was a criminal; he was celebrated because he was a criminal.

The authorities didn’t share in the public’s enthusiasm. He was arrested several times, but he managed to escape custody each time.

However, the law finally caught up with him, and as usual, the law won.

Learn more about “Honest” Jack Sheppard and how he because a sensation in 18th century London, on this episode of Everything Everywhere Daily.

London was a rapidly growing and bustling city in the early 18th century.

It was the largest city in Europe and had become a hub of commerce, politics, and culture.

The streets were crowded and dirty, with open sewers and poor sanitation contributing to frequent outbreaks of disease. Social inequality was pronounced: the aristocracy and rising middle class lived in grand townhouses, while the urban poor crowded into slums like those in St. Giles or Whitechapel.

Crime was rampant, and public executions, such as those held at Tyburn, were popular spectacles.

It was in this environment that Jack Sheppard was born.

Jack Sheppard was born in Stepney, London, in 1702. His family was poor but not criminal. After his father died when Jack was young, his mother struggled to raise him and his siblings. At age 6, he was placed in the workhouse, which was a common fate for impoverished children.

By 14, he was apprenticed to a carpenter named Owen Wood. Jack was initially seen as bright, talented, and trustworthy—hence his nickname, “Honest Jack.”

He proved to be a talented carpenter and served as an apprentice for five years. He might have led an honest life, but his introduction to Elizabeth Lyon, a prostitute from Drury Lane, led him down a different path. Under her influence, Jack began frequenting taverns and eventually turned to petty theft and burglary to supplement his income.

His path veered sharply when he began drinking in taverns in Covent Garden, where he met Joseph “Blueskin” Blake, a highwayman who would become both a companion and a corrupting influence.

Blake, an experienced thief, introduced him to more sophisticated criminal techniques. Together, they committed a series of burglaries across London.

Sheppard was especially skilled at slipping through narrow spaces and removing locks—skills that came from his carpentry training and his 5’4″ and very thin build.

These burglaries are not what made Jack famous…..

Sheppard’s first major arrest came about through betrayal, though not from his accomplice, Blake. In May 1724, Sheppard was arrested following information provided by a man named William Field, who was a local resident of Drury Lane and an acquaintance of Sheppard’s.

Field’s motivation for betraying Sheppard appears to have been because of the growing rewards being offered and Field’s resentment toward Sheppard.

Based on this information, constables located Sheppard at a tavern in Drury Lane. They arrested him and his Lyon and took them to the St. Giles’s Roundhouse, a small, local prison used to hold criminals temporarily before their formal charging and trial.

The St. Giles’s Roundhouse was a circular structure, hence the name “roundhouse”, that served as a holding cell for the parish. It was not designed as a high-security facility but rather as a temporary lockup for minor offenders and those awaiting transfer to more substantial prisons.

Sheppard and Lyon were held in separate upper-floor cells, both lightly guarded.

Using his agility and carpentry skills, Sheppard slipped out of his restraints. According to accounts, he then broke through the ceiling into Lyon’s room, freeing her as well.

From there, he and Lyon made their way to the roof. Using a blanket rope, made of knotted bedsheets, they lowered themselves down the side of the building and slipped away into the dark London streets, undetected until morning.

When the constables discovered the empty cells at dawn, it caused a stir. The newspapers reported the escape with amazement and disapproval, but the public loved it. Sheppard became an immediate folk hero—young, clever, physically gifted, and rebellious.

After his first escape, Sheppard made no effort to flee London. Instead, he resumed his criminal activities with even greater boldness. Alongside his longtime accomplice Joseph “Blueskin” Blake, Sheppard continued robbing homes and shops, including a particularly brazen burglary of a pawnbroker in Drury Lane.

By July 1724, Sheppard had become a known figure to London’s criminal authorities. His second capture came about when he and Elizabeth Lyon were recognized while drinking at a tavern called the Cock and Magpie in Drury Lane. According to contemporary accounts, they were arrested by a group of constables led by a man named Quilt Arnold, who had been actively searching for Sheppard.

This time, both Sheppard and Lyon were taken to the New Prison in Clerkenwell, a more substantial facility than the St. Giles’s Roundhouse. Established in the 17th century, the New Prison was considered more secure than many local holding facilities.

At the New Prison, the authorities took greater precautions with Sheppard, aware of his previous escape. He was placed in a “strong room” on the upper floor of the prison and fitted with manacles.

Undeterred by these measures, Sheppard immediately began planning his escape. He had managed to conceal a nail on his person during his arrest, and this simple tool would prove crucial to his efforts.

Over several days, he painstakingly worked at his manacles, gradually filing through the metal whenever the guards were not watching.

Once freed from his restraints, Sheppard turned his attention to the cell’s window. The opening was protected by a substantial iron bar set firmly into the frame. Using the same nail that had freed him from his manacles, Sheppard managed to work the iron bar loose enough to remove it entirely from the window frame. This created a very narrow opening.

Because of his thin build, he was able to contort his body and squeeze through the opening.

Rather than simply making his own escape and abandoning Elizabeth Lyon to her fate, he chose to help her escape as well. This was no small challenge, as Lyon was considerably larger than Sheppard. Working from the outside of the cell, he methodically widened the opening by further loosening the window frame until it was just large enough for Lyon to squeeze through.

He gathered the blankets and bedding from their cells and fashioned them into a makeshift rope.

Both he and Lyon then used this rope to descend the exterior side of the wall, dropping down into the street below. They completed their escape in the middle of the night, and it was not until the morning check that their absence was discovered, by which time they had vanished.

Following his dramatic escape from New Prison, Jack Sheppard’s fame in London grew even more. Rather than fleeing the city or maintaining a low profile, Sheppard once again became increasingly bold, continuing his criminal activities and even frequenting some of his old haunts in Drury Lane.

This boldness led to his third arrest in early August 1724, less than two weeks after his escape from Clerkenwell. This time, Sheppard was captured while drinking at a tavern in Mayfair.

Authorities had been systematically searching taverns across London, knowing his penchant for celebration after successful burglaries. When apprehended, he reportedly showed little concern, even making light remarks to his captors about his previous escapes.

Given his growing reputation as an escape artist, officials took him to St. Anne’s Roundhouse in Soho, another parish prison considered more secure than some alternatives. His captors made a point of announcing they had taken special precautions to keep him confined, including placing him in a “strong room” on the upper floor.

Despite these measures, Sheppard’s third escape proved remarkably swift. Within just hours of his confinement, he had carefully examined his cell and identified structural weaknesses. Using techniques similar to his first escape, Sheppard focused on the ceiling of his cell, which was made of relatively thin wooden boards.

Working quietly in the night, he managed to pry loose several boards in the ceiling, creating an opening large enough for his slight frame. Once through this opening, he found himself in a loft space above the cells. From there, he made his way to a small window that gave access to the roof.

The ease and speed of this third escape further enhanced Sheppard’s growing legend. London newspapers reported extensively on the event, and public fascination with the young thief continued to grow.

He had become not just a criminal but a celebrity in London, with broadsheets and ballads celebrating his exploits. This fame, however, would contribute significantly to his ultimate downfall.

In September 1724, Sheppard was captured for the fourth time. Despite the substantial reward offered for his capture, his arrest came about almost by accident.

While drinking heavily at a tavern called the Sheers in Clare Market, Sheppard was recognized by a shop owner who had previously been one of his victims. The man alerted a constable who happened to be nearby, and together they apprehended the intoxicated Sheppard without much difficulty.

Given his now-legendary escape abilities, the authorities took extraordinary measures with Sheppard’s fourth imprisonment. He was taken directly to Newgate Prison, London’s most secure facility. There, he was placed in a special cell known as the “Castle,” which was specifically reinforced to hold particularly dangerous or escape-prone prisoners.

He was heavily shackled with iron fetters that bound his legs and chains that secured him to the floor. Additionally, he was placed under constant surveillance, with guards instructed never to leave him unattended.

The seriousness of his situation intensified when Sheppard was quickly brought to trial at the Old Bailey. He faced multiple charges of theft and burglary, with substantial evidence against him for numerous crimes. On September 12, 1724, he was convicted and sentenced to death by hanging, with the execution scheduled for early October.

Despite the heightened security and his dire circumstances, Sheppard managed his most spectacular escape yet on October 15, 1724. Using a small piece of metal he had concealed, he freed himself from his shackles, broke through the ceiling of his cell, navigated through several locked rooms, and ultimately lowered himself from the prison using a blanket rope. This escape, from what was supposed to be London’s most impregnable prison while under death sentence, cemented his status as a folk hero.

However, Sheppard’s freedom would be brief. Despite now being the most wanted man in London, he still failed to leave the city or maintain a low profile. His celebrity status had seemingly made him overconfident. On October 31, 1724, just two weeks after his dramatic Newgate escape, Sheppard was captured for the fifth and final time.

He was discovered drunk at the Sheers tavern in Clare Market—remarkably, the same establishment where he had been captured before. This time, the authorities took unprecedented precautions. He was returned to Newgate, placed in an even more secure cell known as the “Middle Stone Room,” fitted with heavier irons than before, and chained directly to the floor. Armed guards were posted to watch him continuously, and visitors were strictly prohibited to prevent any outside assistance.

On November 16, 1724, Jack Sheppard was taken to Tyburn for public execution. The procession to the gallows attracted one of the largest crowds ever seen in London, with estimates suggesting that 200,000 people lined the streets to catch a glimpse of the famous escape artist. Even on his final journey, there were rumors of planned rescue attempts, though none materialized.

At Tyburn, Sheppard addressed the crowd briefly before his execution, showing the same bravado that had characterized his criminal career.

He was hanged, bringing an end to his short but spectacular life at the age of just 22. To prevent any posthumous escape attempts by his supporters, his body was reportedly placed under guard until burial.

Jack Sheppard’s fame only grew after his death. He became a symbol of resistance to corrupt authority and an emblem of the clever underdog. His story was dramatized in John Gay’s “The Beggar’s Opera” in 1728, and in William Harrison Ainsworth’s novel “Jack Sheppard” in 1839.

His fame even led Parliament to pass laws censoring plays and novels that glorified criminals, fearing they would encourage public sympathy for crime.

Jack Sheppard was brilliant due to his prison escapes, but he was also quite dimwitted because he kept returning to the same behavior that got him captured in the first place.

While undoubtedly a criminal, “Honest Jack” became a folk hero, whose cleverness, charm, and defiance of authority made him an enduring figure in British popular culture.