Dimmock related that at the moment of boarding, Upton had hailed the pirates as though he had long expected them. Upton, for his part, averred that a man had set upon him with a cutlass and felled him to the deck. These irreconcilable testimonies were to run through the entire Admiralty trial: the one depicted him as an accomplice, the other as a seaman compelled under duress.
Prior to these events, he had spent eight-and-twenty years at sea in the service of the Royal Navy, discharging the duties of boatswain or quartermaster. Born in Deptford, he had been bound apprentice to a waterman and, according to the chronicle, had served faithfully, earning an unblemished reputation. The chronicler describes his parents as honest folk who provided him an education suited to their station. He married near his birthplace and lived in respectability with his wife until her demise, which occurred whilst he was at sea. Upon his return, he discovered she had left him encumbered with heavy debts; creditors pressed him hard, and several warrants were issued against him. He thereupon quit the man-of-war and shipped aboard a merchantman bound for Newfoundland. There, a planter hired him for eighteen pounds a year to labor in the fishery and the gathering of furs. He fulfilled a year’s service before obtaining his discharge.
Upton then took himself to New England. In July 1725, he entered on board the merchantman Perry, bound for Barbados. The vessel touched port, was unladen, and received fresh cargo; Captain King intended thereafter to return to England. Upton petitioned to be turned over to the King’s ship Lynn, commanded by Captain Cooper, but King refused to release him. The Perry cleared the Caribbean for England on the 9th of November.
The chronicle fixes the assault by the Night Rambler off Dominica on November 12, 1725. Captain Cooper, master of the pirate sloop, summoned King and four of his hands aboard his own vessel, whilst a party of his crew boarded the Perry. The merchant master thus found himself parted from his company at the very instant his craft was carried. It is in this tumult that both narratives introduce Upton: the one shows him menaced by a pirate, whilst the other has him welcoming the assailants as though he had awaited their coming. The version Upton delivered later, which the record draws from his journal, ran that a pirate ran up to him, knew him again, and threatened him with a cutlass to compel him to cast his lot with them. The rogue, he swore, cried out that he would cut out his liver should he refuse, and struck him down upon the deck. Three other pirates then allegedly forced him to sign their articles: one held a pistol to his forehead, another held one to his ear, whilst a third brandished forks at his breast. He protested, so he claimed, that he had young children in England and wished to see them once more. He added that he had called upon his captain to bear witness that he was no voluntary hand. Whereupon, his name was subscribed to the articles in his stead.
Upton maintained that he had received no share of the plunder, subsisting solely upon ship’s rations and treated in every respect as a pressed man. The account next traces the Perry, now in the hands of the freebooters, to Aruba. The captives were cast upon the island for seventeen days without sustenance, save for such victuals as a surgeon occasionally conveyed to them in secret. On the 10th of December, the pirates sighted a Dutch sloop and made prize of her. Upton and two other men, whom he likewise declared to have been forced, succeeded in making their escape from this vessel.
After sundry misadventures, Upton entered on board the Nottingham, Captain Charles Cotterel, serving two years as quartermaster. He was subsequently apprehended upon an accusation of piracy. His defense rested entirely upon the initial compulsion and his asserted lack of willing participation; yet the three witnesses from the Perry offered a directly contrary portrait.
The first, Dimmock, had been second mate of the Perry. According to his deposition, when the pirates clambered aboard, Upton hailed them, crying: “Here they are, boys! I am glad to see you; I have looked for you a great while.” He swore that the pirates greeted him by his name, that Upton joined in the plundering of the vessel, and that he was made boatswain on the very next morning. Dimmock also related that he was himself scourged with two hundred lashes, and afterwards wounded near the ear by Upton, whom he accused of having twisted the whip and taken a direct part in the violence. These matters rest solely upon the testimony of the second mate, and are nowhere acknowledged in Upton’s own relation.
Dimmock further affirmed that at Aruba, Upton stripped the Perry of her most serviceable rigging, carried these stores aboard the sloop, and kept sundry effects belonging to Furnell, a passenger. He testified moreover that during the council held over the vessel’s fate, Upton opposed returning her to her company, proposing instead to burn her with the captain and the second mate lashed to the mast. This very proposal was put to Upton shortly before his execution; he denied it to the end.
Eaton, chief mate of the merchantman, confirmed the substance of Dimmock’s accusations. He recounted that the pirates demanded whether he would sign their articles; he twice refused. Thereupon, they cast a rope about his neck and hoisted him up until he lost his senses, before lowering him and repeating their threats. When the articles were exhibited, Eaton claimed to have seen Upton’s name, whose hand he knew well. Furnell, a passenger aboard the Perry, corroborated in his turn the preceding depositions. He swore that Upton proved more cruel than the rest of the pirates and carried off everything he could lay hands on in the ship.
Upton pleaded that these three men had borne witness out of malice and resentment. He declared he had proposed to Dimmock to retake the Perry: thirteen pirates were then aboard, said he, and all in their cups, whereas nine captive seamen remained sober. According to him, the second mate declined, deeming the enterprise far too hazardous. Dimmock denied any such colloquy. The contradiction thus remained absolute: the one painted Upton as a mariner dragged along by force, the other as a traitor who awaited the rovers and aided them in gutting his own ship.
The trial came on at the Admiralty Sessions in May 1729. Having heard the three witnesses, the jury returned a verdict of guilty. When the finding was pronounced, Upton turned toward them, demanding what it was they had just done. Under sentence of death, he bore himself with fortitude and penitence, according to the chronicler. He admitted several facts with little evasion, yet persisted in denying that he had ever entered voluntarily with the pirate crew. The chronicler adds that he lamented a dissolute life and exhibited to the last the outward marks of true repentance.
A discrepancy in dates persists within the record itself. Its principal narrative places the taking of the Perry on November 12; Dimmock’s deposition asserts the vessel cleared Barbados on the 12th and was captured on the 14th at noon. The chronicle leaves this divergence unresolved. It records without hesitation, however, the execution of Upton on May 16, 1729, he being then about fifty years of age. Interrogated once more as to the design of burning the Perry with the master and mate aboard, he denied it a final time, and submitted to his fate.