Jack Shepard stood on the roof of St. Giles roundhouse in London, having just broken through the timber ceiling of his cell, and understood that he had only one way down. He tore the cloth from his bed, twisted it into a rope, and lowered himself to the ground. As a crowd gathered at the commotion, he pointed to the rooftop and shouted that the prisoner was still up there, then slipped into the crowd and walked away.
He had been arrested that same day, and it had taken him just three hours to escape. Shepard was born on the 4th of March 1702 in Spitalfields, one of the poorest and most dangerous neighborhoods in London, a place known for the prostitutes and criminals who filled its streets. His father died when Jack was young, and with his mother unable to support him, he was sent to a workhouse at St. Helen’s Bishopsgate at the age of six.
His fortunes improved when he went to work for William Kneebone, a shopkeeper who taught him to read and write and found him an apprenticeship as a carpenter. By the age of twenty, Shepard had become a skilled craftsman, with only a few years of his apprenticeship left. His life seemed to be moving in the right direction. That changed when he met Elizabeth Lyon.
Shepard was small, only five feet four inches, but he was strong, witty, and popular with the women at the local taverns. One tavern owner, Joseph Hayne, encouraged young apprentices to visit his establishment, the Black Lion. The place was full of characters from London’s underworld, and it was there that Shepard’s life took a turn. He became addicted to alcohol and fell into a world of drinking and whoring.
It was in that chaos that he met and fell in love with Lyon, a prostitute. As he neglected his duties as a carpenter, she encouraged him to steal to increase his income. In 1723, Shepard began committing petty theft. He started small, stealing two silver spoons from a tavern while on an errand for his master, then moved on to stealing goods from houses where he was working.
His crimes went unnoticed, but his new lifestyle strained his relationship with Kneebone. On the 2nd of August 1723, with less than two years of his training left, he quit. He gave up carpentry entirely and turned to stealing and burglary to support himself and Lyon. When he was not committing crimes, he was usually drunk at the Black Lion, and it was there that he made an association with a well-known criminal named Jonathan Wild.
Soon after, Shepard began working with Wild and his men, helping to move stolen goods. By then, the authorities had caught up with him and issued a warrant for his arrest. Wild, aware of this and believing Shepard could become a useful player in his gang, sent one of his men, James Sykes, to challenge Shepard to a game of skittles to learn more about him. Instead, Sykes betrayed Shepard, giving a constable information that led to his conviction.
Sykes had nothing against Shepard, but he wanted the £40 reward. Shepard was imprisoned on the top floor of St. Giles roundhouse, knowing he would be found guilty, and with escape his only option, he broke through the ceiling and made his way to freedom. He remained free for a year, but on the 19th of May 1724 he was caught pickpocketing and detained overnight in St.
Ann’s roundhouse. The next morning, Lyon came to visit him, but she was recognized as his wife and accomplice and locked up with him. They were sent to New Prison in Clerkenwell. Shepard had managed to sneak in a file, and after a few days he removed their chains.
The best way out, he believed, was through the window, which was covered by an iron bar. The pair made a small hole in the wall next to the window, loosened the bar, and removed it. Using their bed cloths, they made a rope, climbed out the window, and lowered themselves to the ground. They then faced a wall twenty-two feet tall.
Shepard was very short, and Lyon was a large woman, but the pair managed to get over the wall, and Shepard escaped justice a second time. Shepard continued robbing to make a living and became extremely good at it. Jonathan Wild recognized his abilities and wanted Shepard to sell him all the goods he stole, but Shepard, still angry about what Wild’s man had done to him, refused to cooperate. He became the enemy of Wild, who aimed to get him arrested.
Shepard then teamed up with Joseph Blake, and together they burgled the house of William Kneebone, his former master. Shepard’s buyer of stolen goods was a man named William Field. For months, they had been doing business, and Shepard grew to trust him, unaware that Field was one of Wild’s men. Field told Wild about his arrangement with Shepard, and Wild saw a perfect chance to get him locked away for good.
All he needed was Shepard’s location, so he met with Lyon, took her to a brandy shop, and bought her drinks until she was drunk and talkative. After some persuasion, she betrayed her husband and told Wild where he was. Shepard was arrested for a third time and tried at the Old Bailey on three charges of theft. He was acquitted of the first two for lack of evidence, but there was plenty of evidence concerning the burglary of his former master’s house.
Wild, Field, and Kneebone all testified against him. Found guilty on the 12th of August, he was sentenced to death. Shepard had no intention of facing his punishment. On the 31st of August, after spending time filing at a metal bar in his cell, he finally loosened it but left it in place so the guards would not suspect anything.
When his two visitors arrived, the plan went into motion. One of the women began flirting with the guard, distracting him, which gave Shepard the vital minutes he needed. He removed the metal bar, squeezed through the tight gap thanks to his small frame, changed into women’s clothing his visitors had brought, and walked out of Newgate Prison without anyone suspecting a thing. Shepard had become a hero among the working class.
His Cockney accent, good looks, and ability to escape any prison made him an idol to many. But despite his ability to escape, he kept getting locked away. About a week after his escape, he was found and placed in a cell in Newgate. The guards, noticing tools in his cell, took precautions and moved him into a strong room within the prison called the Castle.
He was clamped in leg irons and handcuffs and chained to the floor. Escaping the Castle was virtually impossible. Six days after his imprisonment, Shepard put his escape plan into action. First, he used a nail to slip off his handcuffs.
With his hands free, he picked the padlock securing the chain to the floor, freeing himself to move around. He decided the best way out was up. He forced several locks, removed metal bars above him, and climbed to the roof of the prison, twenty metres above the ground. He returned to his cell, grabbed his blanket, and once back on the roof, used it to reach a house next to the prison.
He broke in around one in the morning, moved stealthily, and walked out the front door without waking anyone. After days of wearing the leg irons, he convinced a shoemaker to remove them in exchange for a large sum of twenty shillings. Free again, Shepard returned to drinking and whoring. One night he broke into a pawn shop and stole expensive items, including a silk suit, jewelry, and a sword.
He spent his money on two mistresses and lived as a fine gentleman for the night. The next day, on the 1st of November, in the early hours of the morning, he was spotted by police. Too drunk to resist or flee, he was arrested and taken to Newgate, confined to the middle stone room, a cell in the center of the prison guarded at all times. He was put in chains and irons weighing around three hundred pounds.
By this point, he was known throughout the country, and people, especially upper-class ladies, paid shillings just to visit his cell and catch a glimpse of him. He was so famous that King George’s personal painter, James Thornhill, did his portrait. Shepard was once again sentenced to death. Unable to escape his cell, on Monday the 16th of November he was moved from Newgate to the gallows at Tyburn.
As his cart passed through London, huge crowds gathered in support. It seemed they were celebrating him. Over two hundred thousand people, around one third of London’s population, came to watch. His friends had put together a plan to try to revive him after the hanging, hoping a doctor could bring him back, as was possible in rare cases.
But as soon as the strangulation began, the crowd pulled on his legs to give him a quick death. That evening, his body was moved and buried in the churchyard of St. Martin-in-the-Fields in London.