Later, having fallen in with bad company in the slum area of St Giles, he robbed his grandmother of 17 pounds, and spent the evening getting drunk.
Through the efforts of a kindly landlord who took pity on the boy, who he found wandering in the streets dressed in rags, his grandmother was persuaded to take Simms back into her house, but for a month he was kept shackled to the kitchen grate during the day and guarded at night.
More of his acquaintances were transported and, again worried that he might meet the same fate, Simms managed to secure himself a position as a coach driver for an inn-keeper and soon moved on to driving the carriage of a nobleman.
Arriving in Maryland, he was sold as an indentured servant for 12 guineas, but almost immediately escaped, stealing his master's horse and riding for the coast.
The ship was captured by the French, but the crew were ransomed and Simms got work on a man o' war rising to the rank of midshipman.
Simms carried out a series of robberies in London and Epping Forest, but wasted his money on prostitutes and worried for his safety decided to leave for Ireland.
He was transferred to London by a writ of habeas corpus, and having been sentenced to death for highway robbery was committed to Newgate to await execution.
He wrote a thirty-page autobiography entitled The Life of Henry Simms, from his Birth to his Exit and had many women visitors.
On the day of his execution, 17 June 1747, he dressed smartly in clean clothes and, as he mounted the cart which took the prisoners to the gallows at Tyburn, he tossed his shoes into the crowd.