The Lives of RICHARD OAKEY and MATTHEW FLOOD
Street-Robbers and Footpads
The first of these criminals, Richard Oakey, had been by his friends put apprentice to a tailor. In about two years his master failed, and from thence to the day of his unhappy death, Oakey continually followed thieving in one way or other. At first he wholly practised picking of women's pockets, which he said he did in a manner peculiar to himself; for being dressed pretty genteelly, he passed by the person he intended to rob, took up their upper petticoat and cut off the pocket at once, tripping them down at the same time. Then he stepped softly on the other side of the way, walked on and was never suspected. He said that while a lad, he had committed several hundred robberies in this way. As he grew older he made use of a woman to assist him, by pushing the people against the wall, while he took the opportunity of cutting their pockets; or at other times this woman came behind folks as they were crossing the way, and catching them by the arm, cried out, "There's a coach will run over ye"; while Oakey, in the moment of their surprise, whipped off their pocket.
This woman, who had followed the trade for a considerable time, happened one night at a bawdy-house to incense her bully so far as to make him beat her; she thereupon gave him still more provoking language, till at last he used her so cruelly, that she roared out "Murder"; and not without occasion, for she died of the bruises, though the people of the house concealed it for fear of trouble, and buried her privately. Upon this Oakey was obliged to go on his old way by himself.
The robberies he committed being numerous and successful, he bethought himself of doing something, as he called it, in a higher way; upon which, scraping acquaintance with two as abandoned fellows as himself, they took to housebreaking. In this they were so unlucky as to be detected in their second adventure, which was upon a house in Southwark near the Mint, where they stole calicoes to the value of twenty pounds and upwards. For this his two associates were convicted at Kingston assizes, he himself being the witness against them, by which method he at that time escaped. And being cured of any desire to go a-housebreaking again, he fell upon his old trade of picking pockets, till he got into the acquaintance of another as bad as himself, whom they called Will the Sailor. This fellow's practice was to wear a long sword, and then by jostling the gentleman whom they designed to rob, first created a quarrel, and while the fray lasted, gave his companion the opportunity of rubbing off with the booty. But whether Will grew tired of his companion, or of the dangerous trade which he was engaged in, certain it is that he left it off, and got again out of England on ship-board.
Oakey then got acquainted with Hawes, Milksop, Lincoln, Reading, Wilkinson, and half a dozen others, with whom one way or other he was continually concerned while they reigned in their villainies. And as they were in a short space all executed, he became acquainted with Levee, Flood, Blake and the rest of that gang, in whose association he continued until his crimes and theirs brought them together to the gallows. After condemnation his behaviour was such as became his condition, getting up in the night to pray so often and manifesting all the signs of a sincere repentance.
Matthew Flood was the son of a man who kept the Clink Prison in the parish of St. Mary Overys, who had given him as good an education as was in his power, and bound him apprentice to one Mr. Williams, a lighterman. In this occupation he might certainly have done well, if he had not fallen into the company of those lewd persons who brought him to his fate. He had been about three months concerned with Blake, Levee, etc., and had committed many facts.
His behaviour under sentence was very penitent and modest, nor did he suffer the continual hopes his friends gave him of a reprieve ever to make him neglect his devotions. At the place of execution he said he was more particularly concerned for a robbery he had committed on a woman in Cornhill, not only because he took from her a good many guineas which were in her pocket, but that at the same time also he had taken a will which he burnt, and which he feared would be more to her prejudice than the loss of her money.
Oakey was about twenty-five years old at the time of his death, and Matthew Flood somewhat younger. They suffered on the same day with Weaver and the last-mentioned malefactor Levee, at Tyburn.
 The Clink Prison was, until 1745, at the corner of Maid Lane, Southwark. It was originally used as a house of detention for heretics and offenders against the bishop of Winchester, whose palace stood nearby.
Source: Hayward, Lives of the Most Remarkable Criminals