Richard his son had a promising genius, and received a liberal education at St. Paul’s school. But a naturally vicious disposition baffled all restraints. When only nine years old he showed his covetous disposition, by robbing his sister of thirty shillings, and absconding with it. In a few days, however, he was found, brought home, and sent to school, where his vicious propensities were only strengthened by indulgence. Impatient of the confinement of a school, he next robbed his father of a considerable sum of money, and absconded. His father, however, discovered his retreat, and found him a little way from town in the company of two loose women.

Despairing of his settling at home, his father sent him on board a man-of-war, in which he sailed up the straits, and behaved gallantly in several actions. Upon his arrival in England, he left the ship, under the pretence that a younger officer had been preferred before him, upon the death of one of the lieutenants. In a short time he joined a band of thieves, assisted them in robbing the country-house of admiral Carter, and escaped detection. Having at length commenced robber, the first remarkable robbery in which he was engaged, was that of breaking into the house of a lady of Blackheath, and carrying off a large quantity of plate.

He and his associates were successful in selling the plate to a refiner; but in a short time he was apprehended for the robbery, and committed to Newgate. While there, he sent for the refiner, and severely reproached him in the following manner: “It is,” said he, “a hard matter to find an honest man and a fair dealer: for, you cursed rogue, among the plate you bought there was a cup with a cover, which you told us was but silver gilt, buying it at the same price with the rest; but it plainly appeared, by the advertisement in the gazette, that it was a gold cup and cover; I see you are a rogue, and that there is no trusting any body.” Dudley was tried, convicted for this robbery, and sentenced to death: but his youth, and the interest of his friends, procured him a royal pardon.

For two years he conducted himself to the satisfaction of his father, so that he purchased for him a commission in the army. In that situation he also acquitted himself honorably, and married a young lady of a respectable family, with whom he received an estate of a hundred and forty pounds a year. This, with his commission, enabled them to live in a genteel manner. Delighting, however, in company, and having become security for one of his companions for a debt, and that person being arrested for it, one of the bailiffs was killed in the scuffle, and Dudley was suspected of being the murderer.

What strengthened this suspicion was, that Dudley was the avowed enemy of all that class of society. He deemed a bailiff in England, or what is known in Scotland by the name of messenger, as one who is determined to strip every person who comes under his power of all he possibly can.

But, leaving the statements of Dudley concerning these men, let us return to the relation of his actions. Having banished every virtuous feeling, being more inclined to live upon the ruins of his country than the fruits of his industry, and more disposed to fight than to work, he abandoned his own house, and joined a band of robbers. Dudley soon became so expert a robber, that there was scarcely any robbery committed but he acted a principal part in it. Pleased with this easy way of obtaining money, and of supporting an extravagant expense, he also prevailed upon Will, his brother, to join him in this employment. It happened, however, that Will had not been long in his new occupation, when the captain was apprehended for robbing a gentleman of a watch, a sword, a whip, and nine shillings. But, fortunately for him, the evidence was defective, and he escaped death a second time.

Now hardened in vice, he immediately recurred to his old trade. He robbed on the highway, broke into houses, picked pockets, or performed any act of violence or cunning by which he could procure money. Fortune favored him long, and he went on with impunity, but was at last apprehended for robbing Sir John Friend’s house. Upon trial the evidence was decisive, and he received sentence of death. His friends again interposed, and through their influence his sentence was changed for that of banishment. Accordingly, he and several other convicts were put on board a ship bound for Barbadoes. But they had scarcely reached the Isle of Wight, when he excited his companions to a conspiracy, and, having concerted their measures while the ship’s company were under hatches, they went off with the longboat.

No sooner had he reached the shore than he abandoned his companions, and travelled through woods and by-paths. Being in a very mean dress, he begged when he had no opportunity to steal. Arriving, however, at Hounslow heath, he met with a farmer, robbed him, seized his horse, and, having mounted, set forward in quest of new spoils. This was a fortunate day, for Dudley had not proceeded far on the heath when a gentleman, well dressed, and better mounted than the farmer, made his appearance. He was commanded to halt and to surrender. Dudley led him aside into a retired thicket, exchanged clothes and horse, rifled his pockets, and then addressed him, saying, that “he ought never to accuse him of robbing him, for according to the old proverb, exchange was no robbery;” so bidding him good day, he marched off for London. Arrived there, he went in search of his old associates, who were glad to see their friend; and who, in consequence of his fortunate adventures and high reputation among them, conferred upon him the title of captain, all agreeing to be subject to his commands. Thus, at the head of such an experienced and desperate band, no part of the country was secure from his rapine, nor any house sufficiently strong to keep him out. The natural consequences were, that he soon became known and dreaded all over the country.

To avoid capture, and to prevent all inquiries, he paid a visit to the north of England, and, being one day in search of plunder, he robbed a Dutch colonel of his horse, arms, and fine laced coat. Thus equipped, he committed several other robberies. At length, however, he laid aside the colonel’s habit, only using his horse, which soon became dexterous at his new employment. But one day meeting a gentleman near Epsom, the latter resisted the captain’s demands, and discharged his pistol at Dudley. In the combat, however, he was victorious, wounded the gentleman in the leg, and, having stripped him of his money, conveyed him to the next village, that he might receive medical assistance, and then rode off in search of new adventures. The captain and his men were very successful in this quarter. No stage, nor coach, nor passenger, of which they had intelligence, could escape their depredations, and scarcely a day passed without the commission of some notorious robbery.

Captain Dudley and his men went on in a continued course of good fortune, acquiring much wealth, but amassing little, as their extravagance was equal to their gains. On one ill-fated day, however, having attacked and robbed the Southampton coach, they were keenly pursued, and several of them taken, but Dudley escaped. Deprived of the chief part of his own forces, he now attached himself to some housebreakers, and with them continued to commit many robberies; in particular, with three others, he entered the house of an old woman in Spitalfields, gagged her, bound her to a chair, and rifled the house of a considerable sum of money, which the good woman had been long scraping together. Hearing the money clink that was going to be taken from her, she struggled in her chair, fell down upon her face, and was stifled to death, while the captain and his companions went off with impunity. But when the old woman came to be interred, a grandson of hers, who had been one of the robbers, when about to be fitted with a pair of mourning gloves, changed countenance, was strongly agitated, and began to tremble. He was suspected, charged with the murder, confessed the crime, and informing upon the rest, two of them were taken, tried, and condemned, and the three hanged in chains.