Jack Shepherd was born in December 1702 in Spitalfields London the son of a carpenter. His father died when Jack was still young and his mother brought him up in the Bishopsgate workhouse.
Following the workhouse he was apprenticed in his fathers trade of carpenter but he ran away in 1723, he was arrested for this offence. He then turned to theft, pick pocketing and housebreaking, working with an accomplice called Joseph Black known as ‘Taliesin’ .
Shepherd was a heavy drinker and frequented the Black Horse on Drury Lane with several ‘lady friends’ the favourite of which was Elizabeth Lyon known as Edgware Bess.
He was arrested and committed to St Giles Roundhouse for housebreaking in 1724, he escaped through the roof.
The following month he was arrested for pick pocketing and sent to Newgate Gaol, where by chance his mistress Elizabeth Lyon was also imprisoned for a similar offence. The gaolers put them in the same cell believing them to be husband and wife. Friends visited and smuggled a tool into Shepherd which he used to file around one of the bars in their cell until he could remove it. In order to escape they still had a twenty-five foot drop into the yard below. They tied a blanket and a sheet together and tied it to the remaining bar of their cell window, they then climbed over the prison gate, using the bolts and locks as footholds.
After their escape the separated briefly and Jack left for the country, where he may have tried his had at being a highwayman. He soon returned to London and his old ways, housebreaking with accomplices, he injured one of these during a fight over spoils. He also angered Jonathan Wild whose protection he refused, as a result he was arrested and sentenced to death at the Old Bailey.
He was sent back to Newgate and locked in a condemned cell with a solid door, over which was a small opening guarded by iron spikes. A visiting lady friend passed him a tool with which he sawed through the spike. When a group of ladies, including Edgware Bess visited him, he bent the spike and pushed his head and shoulders through the hole, he was then pulled out by his visitors while the guards were busy drinking. The story is that he donned a dress to escape the building.
Shortly afterwards he was spotted walking across Finchley Common and was re-arrested. He was again sent to Newgate, this time he was held in a secure cell and he was manacled with irons at both his hands and his feet, the chains were then fastened to the stone floor.
No one knows how but he managed to free his hands then using a bent nail, freed the leg chains from the floor and wrapped the chains around his legs several times holding them in place with his garters. He attempted to escape through a chimney but found a metal bar across it. With considerable effort he dislodged the bar and used it to knock a hole higher up the chimney to escape into the room above which was unused. He forced the lock and found himself in the passageway that led to the chapel. The entrance door was bolted on the inside. He knocked a hole in the masonry with his bar until he created a hole big enough for him to slip his hand through and draw the bolt.
It was found later that he had forced his way through four more doors to reach an opening that overlooked the prison wall. He used a blanket that he’d brought with him from his cell to lower himself onto the roof of an adjoining house. He stayed there for a while then entered the house through a garret window. At some stage here he managed to remove his leg irons still wrapped around his legs.
Within a very short time he was back to his old ways and robbed a pawn brokers, he proceeds of which he spent in the Black Horse. He was recognised by a young boy who informed the authorities. Shepherd was so drunk that he was barely aware of his arrest.
He was sent back to Newgate, this time the guards took no chances, he was watched night and day, and they charged his visitors sizable fees to visit him. While awaiting execution he even sat for the royal portrait painter Sir James Thornhill.
He did try again, he had obtained a pen knife with which he planned to cut his bonds while in the execution cart and disappear in to the crowd, but the knife was discovered.
His execution drew a crowd of an estimated 200,000 when he was hanged at Tyburn on the 16th November 1724 not yet 22 years old. He was buried at St Martins in the Field church yard.