The Thief Who Escaped His Own Execution Cell

On 15th October 1724, a 22‑year‑old carpenter named Jack Sheppard was chained to the floor of the condemned cell in Newgate Prison — London’s most notorious gaol — awaiting execution for theft. He was about 5’4”, slightly built, and had already escaped from custody multiple times that year. He had a crooked nail.

The Horror

Between about four o’clock in the afternoon and one o’clock in the morning, Sheppard slipped or picked his handcuffs, then used a crooked nail and an iron bar he’d pulled from the chimney to pick or force the padlock on the chain securing him to the floor. He climbed up the narrow chimney of his cell into a disused room above, broke an iron bar along the way, and used it as a tool.

He forced the lock of the long‑unused upper room. Beyond it he found a passage and a series of locked doors. With his improvised crowbar and the nail, he broke through door after door until he reached the prison chapel and then the roof. Contemporary accounts and later retellings count up to six doors between his cell and the outside.

He was still wearing his leg irons. He had no rope. Realising he couldn’t safely drop from the roof, he climbed back down through the chapel, through the broken doors, through the chimney, all the way back into his condemned cell — and collected a blanket.

Then he climbed up again. Using the blanket as a makeshift rope, he slithered down from the prison roof onto a neighbouring building, broke quietly into the house, walked down the stairs, and slipped out through the door into the street, still in irons.

Out in the city, he persuaded a passing blacksmith or shoemaker to remove his leg irons. He was free.

He lasted about two weeks. He broke into a pawnbroker’s or silversmith’s, stole a fine suit, rings, a sword and a wig, and then paraded around Drury Lane and Westminster drinking heavily and showing off. He was rearrested in a tavern, too drunk to resist, still wearing the stolen finery.

Daniel Defoe — the author of Robinson Crusoe and himself once imprisoned in Newgate — is widely credited with ghostwriting Sheppard’s “Narrative,” an autobiographical pamphlet sold at or immediately after the execution.

On 16th November 1724, an enormous crowd lined the route from Newgate to the gallows at Tyburn. Contemporary estimates and later historians commonly give a figure of around 200,000 people — perhaps a quarter to a third of London’s population.

Women in white are reported to have scattered flowers in his path; Sheppard had become a folk hero among the poor. He had hidden a small penknife, hoping to cut the rope after the drop and let the crowd whisk him away, but the guards found it in a final search.

He was hanged at Tyburn at the age of 22. After the drop and the prescribed hanging time, the crowd surged in, cut down his body, and prevented it being taken to surgeons for dissection, smashing the undertaker’s cart in the process. The mob that came to watch him die fought to protect him in death.

The Modern Relic

Newgate Prison has been demolished; the site is now occupied by the Central Criminal Court, the Old Bailey. The condemned cells and old foundations lie beneath or near the modern court complex. The exact chimney Sheppard climbed no longer survives, but the building’s footprint and stories of his escape remain part of London lore.

Tyburn, where Sheppard was hanged, is now the traffic island by Marble Arch; a small plaque on the pavement marks the spot of the gallows.

The expression “Jack the Lad,” meaning a brash, cocky young man who lives recklessly, enters print in the 19th century and is often linked back, at least in spirit, to Jack Sheppard’s legend. The pamphlet narrative attributed to Defoe is still available in print and online.

He was a carpenter who used his trade skills and sheer nerve to escape from what was supposed to be the most secure prison in England, was caught because he couldn’t resist drink and display, and was escorted to the scaffold by a crowd that turned a hanging into a kind of perverse celebration.

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