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In consequence of Jack Sheppard’s desperate character, it was judged expedient by the keeper of the New Prison to load him with fetters of unusual weight, and to place him in a cell which, from its strength and security, was called the Newgate Ward. The ward in which he was confined, was about six yards in length, and three in width, and in height, might be about twelve feet. The windows which were about nine feet from the floor, had no glass; but were secured by thick iron bars, and an oaken beam. Along the floor ran an iron bar to which Jack’s chain was attached, so that he could move along it from one end of the chamber to the other. No prisoner except Edgeworth Bess was placed in the same cell with him. Jack was in excellent spirits; and by his wit, drollery and agreeable demeanour, speedily became a great favourite with the turnkey, who allowed him every indulgence consistent with his situation. The report of his detention caused an immense sensation. Numberless charges were preferred against him, amongst others, information was lodged of the robbery at Dollis Hill, and murder of Mrs. Wood, and a large reward offered for the apprehension of Blueskin; and as, in addition to this, Jack had threatened to impeach Wild, his next examination was looked forward to with the greatest interest.

The day before this examination was appointed to take place — the third of the prisoner’s detention — an old man, respectably dressed, requested permission to see him. Jack’s friends were allowed to visit him,; but as he had openly avowed his intention of attempting an escape, their proceedings were narrowly watched. The old man was conducted to Jack’s cell by the turnkey, who remained near him during their interview. He appeared to be a stranger to the prisoner, and the sole motive of his visit, curiosity. After a brief conversation, which Sheppard sustained with his accustomed liveliness, the old man turned to Bess and addressed a few words of common-place gallantry to her. While this was going on, Jack suddenly made a movement which attracted the turnkey’s attention; and during that interval the old man slipped some articles wrapped in a handkerchief into Bess’s hands, who instantly secreted them in her bosom. The turnkey looked round the next moment, but the manoeuvre escaped his observation. After a little further discourse the old man took his departure.

Left alone with Edgeworth Bess, Jack burst into a loud laugh of exultation.

“Blueskin’s a friend in need,” he said. “His disguise was capital; but I detected it in a moment. Has he given you the tools?”

“He has,” replied Bess, producing the handkerchief.

“Bravo,” cried Sheppard, examining its contents, which proved to be a file, a chisel, two or three gimblets, and a piercer. “Jonathan Wild shall find it’s not easy to detain me. As sure as he is now living, I’ll pay him a visit in the Old Bailey before morning. And then I’ll pay off old scores. It’s almost worth while being sent to prison to have the pleasure of escaping. I shall now be able to test my skill.” And running on in this way, he carefully concealed the tools.

Whether the turnkey entertained any suspicion of the old man, Jack could not tell, but that night he was more than usually rigorous in his search; and having carefully examined the prisoners and finding nothing to excite his suspicions, he departed tolerably satisfied.

As soon as he was certain he should be disturbed no more, Jack set to work, and with the aid of the file in less than an hour had freed himself from his fetters. With Bess’s assistance he then climbed up to the window, which, as has just been stated, was secured by iron bars of great thickness crossed by a stout beam of oak. The very sight of these impediments, would have appalled a less courageous spirit than Sheppard’s — but nothing could daunt him. To work then he went, and with wonderful industry filed off two of the iron bars. Just as he completed this operation, the file broke. The oaken beam, nine inches in thickness, was now the sole but most formidable obstacle to his flight. With his gimblet he contrived to bore a number of holes so close together that at last one end of the bar, being completely pierced through, yielded; and pursuing the same with the other extremity, it fell out altogether.

This last operation was so fatiguing, that for a short time he was obliged to pause to recover the use of his fingers. He then descended; and having induced Bess to take off some part of her clothing, he tore the gown and petticoat into shreds and twisted them into a sort of rope which he fastened to the lower bars of the window. With some difficulty he contrived to raise her to the window, and with still greater difficulty to squeeze her through it — her bulk being much greater than his own. He then made a sort of running noose, passed it over her body, and taking firmly hold of the bars, prepared to guide her descent. But Bess could scarcely summon resolution enough to hazard the experiment; and it was only on Jack’s urgent intreaties, and even threats, that she could be prevailed on to trust herself to the frail tenure of the rope he had prepared. At length, however, she threw herself off; and Jack carefully guiding the rope she landed in safety.

Jack Sheppard in company with Edgeworth Bess escaping from Clerkenwell Prison

The next moment he was by her side.

But the great point was still unaccomplished. They had escaped from the New Prison, it is true; but the wall of Clerkenwell Bridewell, by which that jail was formerly surrounded, and which was more than twenty feet high, and protected by formidable and bristling chevaux de frise, remained to be scaled. Jack, however, had an expedient for mastering this difficulty. He ventured to the great gates, and by inserting his gimblets into the wood at intervals, so as to form points upon which he could rest his foot, he contrived, to ascend them; and when at the top, having fastened a portion of his dress to the spikes, he managed, not without considerable risk, to draw up his female companion. Once over the iron spikes, Bess exhibited no reluctance to be let down on the other side of the wall. Having seen his mistress safe down, Jack instantly descended, leaving the best part of his clothes, as a memorial of his flight, to the jailor.

And thus he effected his escape from the New Prison.