Some inmates were far from “thoughtless,”however, and contrived many ingenious plans of escape. The great heroes of London have often been those who freed themselves from the constraints of Newgate. The greatest of them all, Jack Sheppard, escaped from confinement on six separate occasions; for two centuries he remained a type or symbol of those who elude the practices of oppression with effrontery and bravery as well as skill. It is worth noticing, for example, that a report of the Children’s Employment Commission in the 1840s remarked that poor London children who had never heard of Moses or Queen Victoria had “general knowledge of the character and course of life of Dick Turpin, the highwayman, and more particularly of Jack Shepherd [sic], the robber and prison breaker.”

Jack Sheppard was born in White’s Row, Spitalfields, in the spring of 1702, and then placed in the Bishopsgate workhouse-built on the perimeter of the city, like Newgate itself-before being apprenticed to a carpenter in Wych Street. He broke free of his apprenticeship after six years of industry, even though he was within ten months of completing his terms, and turned to theft for his trade. In the spring of 1724 he was first imprisoned in the St. Giles Roundhouse, but was free within three hours after cutting open the roof and lowering himself to the ground with sheet and blanket. There “he joined a gathering throng” and made his escape through the lanes of St. Giles. A few weeks later he was arrested again, for a pickpocketing offence in Leicester Fields, and was incarcerated in the New Prison of Clerkenwell. He was taken to the “Newgate Ward” there and pinioned with links and fetters of great weight; he sawed through the fetters and somehow cut through an iron restraint before boring his way through an oaken bar some nine inches thick. The severed chairs and bars were afterwards kept by the prison authorities “to Testifie, and preserve the Memory of this extraordinary Event and Villain.”

For three months he was at liberty before being found by the notorious criminal and “thief-taker,” Jonathan Wild; Sheppard was now escorted to Newgate and, after being sentenced to death for three robberies, was consigned to the condemned hold. Even within that dreadful place, by some means or other, he managed to smuggle in a “Spike” and with that began to carve an opening in the wall (or perhaps ceiling); with the help of accomplices on the other side he was dragged out. It was the week of Bartholomew Fair, and he made his escape through the crowds of those going up Snow Hill and Giltspur Street into Smithfield. From there he travelled eastwards into Spitalfields, where he stayed at the Paul’s Head; on an eighteenth-century map, like that of John Roque, it is still possible to track his route. It is in any case a potent image-of a prisoner almost miraculously escaping from incarceration to join the crowds celebrating their own temporary liberty among the booths and shows of Bartholomew Fair.

During the next few days, according to Peter Linebaugh’s The London Hanged, he was seen by a “cobbler in Bishopsgate and a milkman in Islington.” In Fleet Street he entered a watch-maker’s shop and addressed the apprentice there, bidding him “stick to his Tools, and not use his Master to such ill Habits of working so late.” He promptly robbed the premises, but was pursued and taken. Then, once again, he was led to Newgate and in a secluded gaol was “fastened to the floor with double fetters.” Everyone came to see him, and everyone talked about him. He had become a true London sensation, the people “Mad about him” at a time of the greatest “idleness among Meckanicks that has been known in London.” They had all gone to the taverns and ale-houses, in other words, to discuss the prodigy. When certain reverend gentlemen visited his cell he declared that they were “Ginger-bread Fellows” and that “One File’s worth all the Bibles in the world.” The pagan temper of the Londoner is here revealed. “Yes, sir, I am the Sheppard,” he said while in confinement, “and all the jailors in the town are my flock.” A file was found upon him and he was removed to the “Stone Castle” on the fifth storey where he was chained to the floor, his legs secured with irons and his hands cuffed. These instruments were inspected daily, and Sheppard himself was under regular supervision.

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