Sheppard was a petty burglar in London in the 18th Century, and fenced goods via Jonathan Wild. Wild deserves a post of his own, but he essentially was an incredibly corrupt lawman who bought stolen items from theives, and then sold them back to
their owners for a profit. Wild and Sheppard had had a financial disagreement, and so it was conspired to get Sheppard arrested. By providing information as to a known felon's arrest, Wild was also able to make money. So, Sheppard was captured and imprisoned on the top floor of St. Giles's Roundhouse for questioning. Sheppard probably rightly figured that as he'd fallen afoul of Wild he wouldn't stand much of a chance of any leniency. So he resolved to break out.
He fashioned a rope from his bedclothes, broke through the wooden ceiling and lowered himself to the ground still wearing leg irons. By this time a crowd had gathered outside the Roundhouse having noted that someone was escaping. He slipped into the crowd, then pointed at the roof and shouted that he could see someone lurking in the shadows. In the confusion created by his cunning act of misdirection, he made good his escape.
Sheppard seems unable to keep a low profile for long, and soon after he was arrested for pickpocketing and kept overnight in St. Ann's Roudhouse where he was visited by his wife, a woman named Bessie who history primarily records as being large and incredibly busty. Suspecting conspiracy she was detained too and locked in a cell with him. They were then sent to the New Prison in Clerkenwell, where they were locked up together. It seems strange to us to imprison a married couple together, but prison in those days was far less ordered. Prisoners, especially in Newgate were allowed to freely intermingle in enclosures, rape, murder and violence were common. Regardless, the Sheppards soon devised an escape plan. They filed through their manacles, dislodged a bar from the window and again used their knotted bedsheets to make good their descent to ground level. They then stood in front of the imposing prison wall, the only thing standing between them and freedom. What Jack did next laid the foundations of his future fame. He lifted his wife onto his shoulder and using a nearby gate scrabbled and climbed up the ironwork managed somehow managed to reach the summit. He then, acrobatically (or as acrobatically as one can be with your wife over your shoulder) rapidly descended to the street; and freedom.
Of course, these escapes only served to inflame Wild, and being on the wrong side of this man was not a recipe for an easy life in London at this time. A man of immense resources and grasp, Wild soon ensured that Sheppard was captured and quickly tried. Wild sat in the witness box across from Sheppard directly giving evidence against him, and the verdict was a predictable one: death. The date for execution was set for 4th September. Imprisoned in Newgate, on 31st August, Sheppard resolved to escape once more. They key was a window in the cell which allowed the prisoner to talk to visitors or legal representatives. He set to work in dislodging one of the bars of the door and with the collusion of some friends and Besse (who hadn't be rearrested) he squeezed through the tiny gap in the bars. His wife provided him with a convincing disguise; dressing him up in her clothes as a woman and he waltzed daintily past the unsuspecting guards.
Having made three daring escapes (and non-violent ones at that) he had become somewhat of a celebrity. His profile made it hard for him to keep a low profile, and it wasn't long before he was re-arrested by a posse from Newgate after briefly leaving London. Sheppard was returned to the condemned cell at Newgate once more. His fame had increased to such a level that nobles and other movers and shakers visited him in Newgate to marvel at him. Respect for him had increased to such a level that these esteemed visitors tried slipping him files and escape tools, but they were discovered by the guards. As a result, he was transferred to a strong room in Newgate prison known as the "Castle", clapped in sturdy leg irons and chained down to two metal staples set into the floor.
Showing off, he demonstrated how easily it was for him to escape by picking the lock of his padlocks in front of the guards. As a result, he was bound even more tightly. He seems to have been relishing his celebrity by this point, and is recorded as saying:
"I am the Sheppard, and all the Gaolers in the Town are my Flock, and I cannot stir into the Country, but they are all at my Heels Baughing after me."
But maybe he had a right to be cocky, as he was about to boggle and astonish his gaolers and ensure his place in history. Wild had betrayed one of his lieutenants (a fellow called Blueskin), and whilst giving evidence against him Blueskin had leapt across the courtroom and tried to slash Wild's throat. He was lucky to escape with his life. This attempt to murder Wild sent the prison into an uproar - he was loathed as he had betrayed many of the men behind the prison's sturdy walls.
Sheppard saw his chance. He picked the lock of his handcuffs and removed the chains. He quickly realised he wasn't able to free himself of the bulky and awkward leg irons, so they he would have to escape wearing them. His plan was to climb up the sooty and claustrophobic chimney, see how far he could get and then improvise from there. Halfway up he encountered an iron bar set across the chimney blocking his progress. Somehow he removed the bar, and used it to smash through the ceiling into the "Red Room" which was used to house aristocratic political prisoners. He dropped down into the room (still wearing leg irons). But this was still a prison, and with it a selection of locked and bolted doors. Through a combination of delicate lockpicking and brute force using his crowbar he broke through door after door, six in all, all in the pitch dark and with the prospect of being caught at any time by a patrolling guards.
Sheppard eventually found himself standing in the cold night air of London on the roof of the prison. The sweet, fresh air must have seemed like a tonic after the filth of the prison. One problem though, he may be outside, but he was sixty feet above the ground. There was no way down.
Most men would have admitted defeat there, but not Sheppard - he went back through darkened corridors of the prison, back through the locked doors, up through the ceiling of the Red Room, crawled all the way back down the chimney into his cell and took the blanket from his bed. He then (still wearing the leg irons I remind you) went all the way back to the roof, and using his blanket as a makeshift swing made it over the walls landing softly on the roof of an adjacent house. He broke into the house, and stealthily made his way through the building past the sleeping occupants and into the street. He then got his leg irons removed by spinning a sob story to passing shoemaker. Freedom once more!
By this time Sheppard was really starting to revel in his infamy. He broke into a pawnbrokers and robbed it of all its cash and then dressed himself in a a black silk suit, a silver sword, rings, watches and a wig. In his dandified outfit and
accompanied by two comely maidens he proceeded to go on a what can only be described as a bender. He got hammered at every bar he went to, mostly being given free drinks by people awed by his celebrity. He was finally arrested, blind drunk "in a handsome Suit of Black, with a Diamond Ring and a Cornelian ring on his Finger, and a fine Light Tye Peruke".
They weren't taking any chances with him this time. He was kept and observed at all times in Newgate and loaded with 300lb of iron weights (the actual irons are pictured below). His celebrity had grown so much that his gaolers charged visitors 4 shillings to visit him. Petitions were sent to the King urging him to commute the death sentence to transportation.
Contemporary reports state:
"The Concourse of People of tolerable Fashion to see him was exceeding Great, he was always Chearful and Pleasant to a Degree, as turning almost everything as was said onto a Jest and Banter."
He was also noted to have said to a visiting priest: "One file's worth all the Bibles in the World".
But he was not to escape the gallows again. On 16th November he was taken to Tyburn for the grisly sentence to be carried out. True to form, he had a plan to get out of this one, having a pen-knife concealed on him that he would use to cut the ropes binding him, but it was found by his guards.
The procession to the place of execution was one of the biggest events in London up to that time. As much as 200,000 people showed up to send him off, and after the customary pint of ale given to a condemned man at the City of Oxford Tavern he was sent to the gallows. He took 15 minutes to asphyxiate to death, and after his body was cut down the crowd rushed forward to get a piece of the escape artist that charmed London. Eventually his body was recovered, having been mauled by the crowd, and the broken remains buried in St. Martins-in-the-Fields later that day.
Truly an astonishing series of exploits, humiliating the establishment at every turn. His notoriety after his death was such that usage of his name to promote a play or book was banned for years afterwards. His tale is all the more notable due to his non-violent methods. Of course one cannot say what he would have done had he found a guard on his escape route, but among the tarnished reputations of many of London's 'lovable' rogues Sheppard seems to stand as one of the more daring, and a person that can genuinely be admired for his persistence, and for his refusal to be confined by a corrupt system.
