5 – Jack Sheppard (1702 – 1724)
During his extremely short life and career, Sheppard gained a reputation not only as a highwayman but also as an extraordinary escape artist. Like the vast majority of thieves during the era, Sheppard was born into extreme poverty. He was surrounded by death from an early age as his father and sister died while he was still only a boy. Because of their desperate circumstances, Sheppard’s mother sent him to a workhouse when he was just six years of age.
He became an apprentice to a cane-chair maker until his new master died. Sheppard ended up working for another cane-chair manufacturer who treated him extremely poorly. After a few hard years, he worked as a shop boy for a wool draper called William Kneebone. Sheppard’s mother had been in Kneebone’s employee for years, and this man taught his new apprentice how to read and write.
Sheppard’s criminal career was brief and memorable. He worked as a carpenter until 1722, and the diminutive young man (he was around 5ft 4 inches tall) showed great potential and had just one year left in his apprenticeship. His life changed when he started to frequent the infamous Black Lion Tavern which was the haunt of many criminals in London. It was there that he met and fell for a prostitute named Elizabeth Lyon.
Soon, he threw himself into the world of drinking, whoring, and crime and started to shoplift to supplement his income. His carpentry suffered, and he quit his master’s employ in August 1723. By now, he had graduated to grander crimes including burglary. Initially, at least, Sheppard was able to avoid detection, and as he still worked as a journeyman carpenter, he was able to steal goods from the homes he worked in. He also became acquainted with notorious gang leader Jonathan Wild.
Over the next year, Sheppard became famous for his ability to escape detention. On four occasions, he escaped from prison. The second escape on August 30, 1724, was the first time he escaped while under a death sentence. His most famous escape act occurred on October 15, 1724, when he slipped off his handcuffs, picked his chain with a nail, scaled the roof of Newgate Prison and used his bedsheet to slide onto another roof before finally escaping through the front door. However, his fondness for alcohol caught up with him and two weeks after his Newgate escape; he was caught because he was too drunk to resist arrest.
The day of his execution, November 16, 1724, was a dramatic occasion as an estimated 200,000 people made their way to Tyburn to see the folk hero die. As it turned out, the crowd’s affection for Sheppard foiled his last daring escape plan. The route to his execution was lined with weeping women in white who threw flowers at the condemned man. The Houdini of his day had no intention of surrendering meekly and hatched a daring plan with his publisher Appleby and the famed writer Daniel Defoe.
After a hanging, the body was traditionally left dangling for 15 minutes, and in rare cases, the person could survive. The idea was to retrieve the body and try to revive him. Sadly for Sheppard, his adoring crowd had no way of knowing this so when the trap door opened, they rushed forward and pulled on his legs to ensure their hero died swiftly.