At length James Sykes, otherwise called Hell-and-Fury, one of Sheppard’s companions, meeting with him in St. Giles’s, enticed him into a public-house, in the hope of receiving a reward for apprehending him; and while they were drinking Sykes sent for a constable, who took Jack into custody, and carried him before a magistrate. After a short examination, he was sent to St. Giles’s round-house; but he broke through the roof of that place and made his escape in the night.

Within a short time after this, as Sheppard and an associate, named Benson, were crossing Leicester Fields, the latter endeavoured to pick a gentleman’s pocket of his watch; but failing in the attempt, the gentleman called out “A pickpocket!” on which Sheppard was taken, and lodged in St. Ann’s round-house, where he was visited by Edgeworth Bess, who was detained on suspicion of being one of his accomplices. On the following day they were carried before a magistrate, and some persons appearing who charged them with felonies, they were committed to the New Prison; but as they passed for husband and wife, they were permitted to lodge together in a room known by the name of the Newgate ward. They were here visited by many of their friends, Blueskin among the number; and being provided by them with the implements necessary to enable them to escape, Jack proceeded to secure the object which he had in view with that alacrity and energy which always characterised his actions. The removal of his fetters by means of a file was a work which occupied him a very few minutes, and he then, with the assistance of his companion, prepared for flight. The first obstacle which presented itself to them was in the shape of the heavy cross-bars which defended the aperture, by which light and air were admitted to their cell; but the application of their file soon removed the difficulty. There was then another point of a more dangerous character to overcome—the descent to the yard. Their window was twenty-five feet in height, and the only means of reaching the earth was by the employment of their blankets as ropes. These, however, would not enable them to touch the ground; but they found that there was a considerable distance for them to drop, even after they should have arrived at the extreme end of their cord. Gallantry induced our hero to give the first place to Bess, and she, having stripped off a portion of her clothes, so as to render herself lighter, descended in perfect safety. Jack followed, and they found some consolation in their being at least without the gaol, although there were yet the walls of the yard to climb. These were topped with a strong chevaux de frise of iron, and were besides twenty-two feet high; but passing round them until they came to the great gates, the adventurous pair found means by the locks and bolts, by which they were held together, to surmount this, apparently the greatest difficulty of all, and they once again stood on the open ground outside the gaol. Bess having now re-assumed the clothes, of which she had denuded herself, in order that she might be the more agile in her escape, and which she had taken the precaution to throw over the wall before her, she and her paramour, once more enjoying the free air of liberty, marched into town.

It may readily be supposed that our hero’s fame was increased by the report of this exploit, and all the thieves of St. Giles’s soon became anxious to become his “palls.” He did not hesitate to accept the companionship of two of them, named Grace, a cooper, and Lamb, an apprentice to a mathematical instrument maker; and at the instigation of the latter they committed a robbery in the house of his master, near St. Clement’s church, to a considerable amount. The apprentice, however, was suspected, and secured, and being convicted, received sentence of transportation. Our hero meanwhile escaped, and joining with Blueskin, they did not fail in obtaining considerable booty. The mode of disposing of the plunder which they adopted was that of employing a fellow named Field to procure them a market; and having committed the robbery at Kneebone’s, already mentioned in Blake’s memoir, they lodged its proceeds in a stable, which they had hired, near the Horse Ferry, Westminster. Field was applied to, to find a customer for the property, and he promised to do so, and was as good as his word; for breaking open the stable, he carried off the goods himself, and then conveyed information of the robbery to Wild, alleging that he had been concerned in it. Blueskin, it will have been seen, was tried and convicted for the robbery, and suffered execution; and Sheppard having also been secured, he too was sentenced to death.

On Monday, 30th August, 1724, a warrant was sent for his execution, together with that of some other convicts, but neither his ingenuity nor his courage forsook him upon this, any more than upon any previous occasion. In the gaol of Newgate there was a hatch within the lodge in which the gaolers sat, which opened into a dark passage, from which there were a few steps leading to the hold containing the condemned cells. It was customary for the prisoners, on their friends coming to see them, to be conducted to this hatch; but any very close communication was prevented by the surveillance of the gaolers, and by large iron spikes which surmounted the gate. The visits of Edgeworth Bess to her paramour were not unattended with advantage to the latter, for while in conversation, she took the opportunity of diverting the attention of the gaoler from her, while she delivered the necessary instruments to Sheppard to assist him in his contemplated escape. Subsequent visits enabled Jack to approach the wicket; and by constant filing he succeeded in placing one of the spikes in such a position as that it could be easily wrenched off. On the evening on which the warrant for his execution arrived, Mrs. Maggott, who was an immensely powerful woman, and Bess, going to visit him, he broke off the spike while the keepers were employed in drinking in the lodge, and thrusting his head and shoulders through the aperture, the women pulled him down, and smuggled him through the outer room, in which the gaolers were indulging themselves, into the street. This second escape not a little increased his notoriety; but an instant pursuit being made, he was compelled to lie close. Consulting with one Page, a butcher, it was determined that they should go to Warnden, in Northamptonshire, together where the relations of the latter lived; but on arriving there, being treated with indifference, they immediately retraced their steps to London.

On the night after their return, they were walking through Fleet-street, when they saw a watchmaker’s shop attended only by a boy, and having passed it, they turned back, and Sheppard, driving his hand through the window, stole three watches, with which they made their escape. They subsequently retired to Finchley for security; but the gaolers of Newgate gaining information of their retreat, took Sheppard into custody, and once more conveyed him to “The Stone Jug.”

Such steps were now taken as it was thought would be effectual to prevent his future escape. He was put into a strong room, called the Castle, handcuffed, loaded with a heavy pair of irons, and chained to a staple fixed in the floor. The curiosity of the public being greatly excited by his former escape, he was visited by great numbers of people of all ranks, and scarce any one left him without making him a present in money. Although he did not disdain these substantial proofs of public generosity, which enabled him to obtain those luxuries, which were not provided by the city authorities for his prison fare, his thoughts were constantly fixed on the means of again eluding his keepers; and the opportunity was not long wanting when he might carry his design into execution.

On the fourteenth of October, the sessions began at the Old Bailey, and the keepers being much engaged in attending the Court, he thought rightly, that they would have little time to visit him, and, therefore, that, the present juncture would be the most favourable to carry his plan into execution. About two o’clock in the afternoon of the following day, one of the keepers carried him his dinner; and having carefully examined his irons, and found them fast, he left him. Sheppard now immediately proceeded to the completion of the great work of his life, his second escape from Newgate; in describing which we shall extract from Mr. Ainsworth’s work of “Jack Sheppard,” in which that gentleman has given a lasting fame to our hero, and has founded a most interesting romance on the real circumstances of the life of this daring and extraordinary offender. He says, “Jack Sheppard’s first object was to free himself from his handcuffs. This he accomplished by holding the chain that connected them firmly between his teeth, and, squeezing his fingers as closely together as possible, he succeeded in drawing his wrists through the manacles. He next twisted the heavy gyves round and round, and partly by main strength, partly by a dexterous and well-applied jerk, snapped asunder the central link, by which they were attached to the padlock. Taking off his stockings, he then drew up the basils as far as he was able, and tied the fragments of the broken chains to his legs, to prevent them from clanking, and impeding his future exertions.” Upon a former attempt to make his way up the chimney, he had been impeded by an iron bar which was fixed across it, at a height of a few feet. To remove this obstacle, it was necessary to make an extensive breach in the wall. With the broken links of the chain, which served him in lieu of more efficient implements, he commenced operations just above the chimney-piece, and soon contrived to pick a hole in the plaster. He found the wall, as he suspected, solidly constructed of brick and stone; and, with the slight and inadequate tools which he possessed, it was a work of infinite skill and labour to get out a single brick. That done, however, he was well aware the rest would be comparatively easy; and as he threw the brick to the ground, he exclaimed triumphantly, “The first step is taken—the main difficulty is overcome.”

“Animated by this trifling success, he proceeded with fresh ardour, and the rapidity of his progress was proclaimed by the heap of bricks, stones, and mortar, which before long covered the floor. At the expiration of an hour, by dint of unremitting exertion, he made so large a breach in the chimney that he could stand upright in it. He was now within a foot of the bar, and introducing himself into the hole, he speedily worked his way to it. Regardless of the risk he ran by some heavy stones dropping on his head or feet,—regardless also of the noise made by the falling rubbish, and of the imminent risk to which he was consequently exposed of being interrupted by some of the gaolers, should the sound reach their ears, he continued to pull down large masses of the wall, which he flung upon the floor of the cell. Having worked thus for another quarter of an hour, without being sensible of fatigue, though he was half stifled by the clouds of dust which his exertions raised, he had made a hole about three feet wide and six high, and uncovered the iron bar. Grasping it firmly with both hands, he quickly wrenched it from the stones in which it was mortised, and leapt to the ground. On examination it proved to be a flat bar of iron, nearly a yard in length, and more than an inch square. ‘A capital instrument for my purpose,’ thought Jack, shouldering it, ‘and worth all the trouble I have had in procuring it.’ While he was thus musing, he thought he heard the lock tried. A chill ran through his frame, and grasping the heavy weapon, with which chance had provided him, he prepared to strike down the first person who should enter his cell. After listening attentively for a short time without drawing breath, he became convinced that his apprehensions were groundless, and, greatly relieved, sat down upon the chair to rest himself and prepare for future efforts.

“Acquainted with every part of the gaol, Jack well knew that his only chance of effecting an escape must be by the roof. To reach it would be a most difficult undertaking. Still it was possible, and the difficulty was only a fresh incitement. The mere enumeration of the obstacles which existed would have deterred any spirit less daring than Sheppard’s from even hazarding the attempt. Independently of other risks, and the chance of breaking his neck in the descent, he was aware that to reach the leads he should have to break open six of the strongest doors of the prison. Armed, however, with the implement he had so fortunately obtained, he did not despair of success. ‘My name will not only be remembered as that of a robber,’ he mused, ‘but it shall be remembered as that of a bold one; and this night’s achievement, if it does nothing else, shall prevent me from being classed with the common herd of depredators.’ Roused by this reflection, he grasped the iron bar, which, when he sat down, he had laid upon his knees, and stepped quickly across the room. In doing so, he had to clamber up the immense heap of bricks and rubbish which now littered the floor, amounting almost to a cart-load, and reaching up nearly to the chimney-piece; and having once more got into the chimney, he climbed to a level with the ward above, and recommenced operations as vigorously as before. He was now aided with a powerful implement, with which he soon contrived to make a hole in the wall.

“The ward which Jack was endeavouring to break was called the Red-room from the circumstance of its walls having once been painted in that colour: all traces of which, however, had long since disappeared. Like the Castle, which it resembled in all respects, except that it was destitute even of a barrack bedstead, the Red-room was reserved for state prisoners, and had not been occupied since the year 1716, when the gaol was crowded by the Preston rebels. Having made a hole in the wall sufficiently large to pass through, Jack first tossed the bar into the room and then crept after it. As soon as he had gained his feet, he glanced round the bare black walls of the cell, and, oppressed by the misty close atmosphere, exclaimed, ‘I will let a little fresh air into this dungeon: they say it has not been opened for eight years, but I won’t be eight minutes in getting out.’ In stepping across the room, some sharp point in the floor pierced his foot, and stooping to examine it, he found that the wound had been inflicted by a long rusty nail, which projected from the boards. Totally disregarding the pain, he picked up the nail, and reserved it for future use. Nor was he long in making it available. On examining the door, he found it secured by a large rusty lock, which he endeavoured to pick with the nail he had just acquired: but all his efforts proving ineffectual, he removed the plate that covered it with the bar, and with his fingers contrived to draw back the bolt.