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1724 in London, United Kingdom

Jack the Lad

Legend - told by Victoria Dainton

Born into a poor family, Jack’s father was a carpenter that passed away when he was only a little boy. His mother, unable to support her family without his income, sent Jack off to a workhouse when he was six. He began to learn a trade through carpentry, and by age 20 he was showing great promise. However, this is where Jack’s story really starts to be told.

A small man with a slight stutter, Jack was deceptively strong for his stature and had a quick wit which made him very popular in the taverns. One night, he met a prostitute by the name of Edgworth Bess who would change his life forever.

Quickly it was becoming more enjoyable spending the evenings with Bessy in various taverns than the dull drudgery of the apprenticeship. She taught him to shoplift, which he quickly progressed further by stealing from the houses where he worked. She introduced him to Wild, a London underworld figure notable for operating on both sides of the law. Eventually Jack was accepted as part of Wild’s gang, and turned his attention to burglary.

Leaving the apprenticeship behind, Jack and Bessy got married, and moved to Piccadilly. Bess had been arrested not long after the move, and when Jack had been refused to visit her, he broke in to the Roundhouse and took her away.

His luck turned shortly after that, when Bess, Jack and Jack’s brother Tom committed a burglary together in Clare Market. Tom had a previous conviction, and fearful that he would be hanged this time, he informed on his brother and a warrant was issued for Jack’s arrest.

It was Wild that was instructed to ascertain Jack’s whereabouts, and he managed to get one of his men to betray Jack for £40. They picked him up and dragged him to the same roundhouse Bess had been locked up in pending further questioning. However, Jack was by no means in the mood to be questioned, so he broke through the timber ceiling, fashioned a rope out of bedclothes and lowered himself to the ground. The sounds of him breaking out had attracted a crowd, and as he was still wearing irons, their attention started to turn to him. He subtly joined the crowd, pointed to the roof and shouted he could see the escapee, pointing to the shadows on the roof before swiftly departing.


The second time he was arrested, he was caught in the act of picking a pocket near Leicester Square. Bess tried to visit him in the roundhouse, only to be arrested herself and placed in the cell with him. They were both shipped off to prison in Clerkenwell, sharing a cell as husband and wife. They were only in for a matter of days, after successfully filing through their manacles, removing a bar from the window and used their bed-clothes to lower themselves to the ground.

Jack, a small man with a pale face and large, dark eyes, and Bessy the large buxom prostitute clambered over a 22-foot high prison gate to freedom. Their feat did not go unnoticed by the public, or Wild who admired Jack’s thieving abilities. He proposed they work together, however Jack refused, and began working with Blueskin, a notorious highwayman instead.

They returned to where Jack had worked as an apprentice and robbed his previous master at the dismay of Wild. He would not permit Jack to continue outside his control and sought for his arrest. He suspected Bess if anyone would know of Jack’s whereabouts, so he took her to a brandy shop and plied her with drinks until she betrayed her husband. Jack was arrested for a third time where he was sentenced to death after Wild gave evidence against him.

Four days before his execution, Bess and another woman came to visit Jack. They distracted the guards whilst Jack loosened the iron bars in a window used when talking to visitors. He managed to climb through the gap, and disguise himself in women’s clothing, before making his escape.

At this point in time Jack had become Gentleman Jack, or Jack the Lad, a working class cockney hero to the masses. He managed to evade capture by Wild and his men for some time, but was eventually arrested again. His non-violent and famous escapes had made him very popular, and many visited him in his cell. On two separate occasions were his escape plans thwarted when the guards found files and various tools in his cell. As a result, they transferred him to a strong-room, clapped in leg irons and chained to staples in the floor. After demonstrating how easy it was for him to unlock the horse padlock with a small nail, they bound him more tightly and handcuffed him.

 Blueskin was tried, with the evidence provided by Wild, and although their accounts were not consistent with the evidence given at Jack’s trial, Blueskin was convicted anyway.

As Jack planned his escape from prison and dreamt of freedom, his partner Blueskin was arrested by Wild and his men. They caught Jack’s brother Tom the following day. Blueskin was tried, with the evidence provided by Wild, and although their accounts were not consistent with the evidence given at Jack’s trial, Blueskin was convicted anyway.

Angered and enraged, Blueskin jumped for Wild in the courtroom, slashing his throat with his pocket-knife. There was uproar in the courtroom, but Wild survived the attack. Meanwhile, Jack could hear the commotion which had spread to the prison next door and continued well into the night. He ceased the opportunity, unlocked his handcuffs and removed the chains from his body. Unable to unlock his leg irons, Jack attempted to climb up the chimney only to find his path block by an iron bar. After a few attempts, Jack had managed to break off the iron bar and proceeded to use it to break into the ceiling of the room above.

Still shackled by his leg irons, Jack broke through six barred doors into the prison chapel, then up to the roof 60 feet above the ground. Realising he wouldn’t be able to survive the fall, he went back down to his cell to retrieve his blanket. He then returned to the prison roof and used the blanket to reach the roof of an adjacent house. He broke into the house, snuck down the stairs and out into the street without disturbing the occupants’ sleep.  

He ran through the streets of London until coming across a cowshed in Tottenham where he sought shelter. However, when he was spotted by the barn’s owner he had to be quick on his feet. He managed to convince the owner that he had escaped from prison after being sent there for failing to support a bastard son. He used the same story on a passing shoemaker and persuaded him to help him remove his leg irons, which were later recovered in one of his mistresses’ rooms. Gentlemen Jack had struck again, and everyone was astonished.

Unfortunately, Jack’s period of liberty was to be short-lived. He disguised himself as a beggar, returning to the city and broke into a pawnbroker’s shop, taking a fine suit, sword, jewellery and a wig. Dressed as a fine gentleman, Jack used the proceeds to paint the town with two of his mistresses. He was arrested in the early morning, blind drunk and transported back to prison.

He was detained in the middle of the prison so he could be observed at all times, and loaded with 300 pounds of weights to deter his escapes. Gaolers charged high society visitors to see him with their own eyes and the King’s painter was commissioned to paint his portrait. Many prominent people petitioned to have his sentence of death commuted.

He was offered a reduced sentence if he were to inform on his associates but refused, consequently confirming the death sentence. The following day, Blueskin was hanged.

Jack was taken to the gallows at Tyburn to be hanged. He had one more trick up his sleeve, intending on using his pocket knife to cut the ropes binding him on the way to the gallows, however a guard found it shortly before he left the prison.

The streets of London were crowded as the bell rang. The procession passed through with Jack’s cart drawn along Holborn and Oxford Street. Crowds of up to 200,000 people were there to celebrate Jack’s life and see the man with their own eyes. The procession halted at a tavern and Jack took his last drink. It was like a carnival, the streets filled with merry people many of them purchasing his autobiography that was for sale.


He was left hanging for 15 minutes before his body was cut down. Jack’s friends were ready to take his body to a doctor in an attempt to revive him, but the crowd had pushed forward to stop his body being removed fearing dissection. His remains were badly mauled and left there until later that evening, when what was left of Jack was removed and buried in a churchyard.

Wild lost a lot of control of his gang whilst recovering from Blueskin’s attack in the courtroom. His duplicity became known and many of his men turned on him, providing evidence against him in court. After he had attempted suicide, his story finished in the same way as Jack’s and Blueskin’s, he too was hanged at Tyburn before a massive crowd. What happened to Bess, and if she was there to witness Jack’s, Blueskin’s or Wild’s demise remains a mystery.

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