Henry Simms (aka Gentleman Harry) 1717-1747
(Monarch: George I to George II)
Henry was born in St Martin-in-the-Fields in 1716. Sadly, his parents died before he was five years old, and his grandmother brought him up (apparently a dissenter, meaning someone who didn't conform to the practices of the Church of England but was still a protestant).
Grandma Simms tried to do everything right for Henry. She lived in St James's Parish in Westminster and was the widow of a commissioned officer, so she had a decent pension (which Henry eventually robbed). With such a concerned grandmother, Henry was given a good education, learning French, Latin, maths, and how to read and write.
But despite this, it seems Henry was destined to become a thug because by the age of ten, he had given 'a specimen of his dishonest disposition' when his grandmother took him to visit Mr Palmer, a soap boiler (i.e. a soap maker, which was a very skilled profession – but you've got to wonder about his name and whether he is, in any way, connected to Palmer's soap who now make the much-loved body lotion).
He stole twenty shillings from the till in the shop and apparently got a good hiding for his cheek – not that this put him off!
This early start to his criminal career was his point of no return. Henry went straight into stealing money from his grandmother on several occasions.
And in Henry's own words, he 'began to show an early inclination to vice, without an opportunity of committing it.' Henry's pilfering saw him taken out of school and sent as an apprentice to a breeches maker. He didn't like this very much, especially as he claims he was beaten quite a lot for being lazy, wicked, and unruly.
After running away from his breeches-making apprenticeship, which Henry probably found a bit pants, he generally had a wild time with the wrong crowd. Although he may have thought he'd made some friends, every time he stole something from Grandma Simms (poor old lady, truly), the gang he drank and debauched with stole everything from him. There was certainly no honour amongst thieves – and so Grandma's money and belongings didn't even manage to supply her grandson with anything but a dishonourable bunch of bandits for company.
Eventually, after trying a few different jobs, Henry escalated his career to the noble art of highway robbery. With his education and accent, he became known as Gentleman Harry in the underworld.
I bought a silver-hilted sword for myself, had several new suits of clothes made, particularly one suit of black velvet, and appeared at my usual haunts with my surprising éclat. It was at this time I gained the name of gentleman Harry, for though I was before only called plain Harry, yet, on this my sudden grand appearance, I was styled gentleman Harry, which name I retained for ever.
With his new reputation, Gentleman Harry went on to rob quite a few people in Blackheath. One report of his activities reads:
Simms robbed a gentleman of his watch and seventeen pounds on Blackheath, and likewise robbed a lady of a considerable sum near the same spot. Being followed to Lewisham, he was obliged to quit his horse, when he presented two pistols to his pursuers, by which he so intimidated them as to effect his escape, though with the loss of his horse.
And Simms provides us with an account in his own words:
Another version of these events, in Simm's own words (and easier to read):
I robbed a lady in her coach, on Blackheath. After this robbery, riding down the hill that leads to Lewisham wash, I was overtaken by six or seven butchers, one of whom, seizing the cape of my coat, pulled me off my horse, and the cape giving way, he tore it quite off. I then pulled out my pistols, swearing I would shoot the first man that dared to advance; which none of them cared to do. I retreated into the fields, and got off with the loss of my horse, which cost me seventeen pounds. But I was not long without a horse, for, going towards Bromley, I met a gentleman on horseback, to whom I presented my pistols, ordering him to dismount or I would shoot him through the head, which he did, and I took from him eight guineas and seventeen shillings in silver, and, mounting the horse left him to pursue his journey on foot.
Henry Simms was tried several times for various thefts between 1745 and 1747. He was even transported to Maryland in America (where a vast majority of convicts were sent before Australia was the favourite option) after assaulting a prostitute and robbing a baker's shop, but he escaped back to England through some cunning trickery, theft, bribery, and a two-month journey back to our shores.
Quite the opportunist, not just with crime but with his ability to wriggle out of precarious situations, Gentleman Harry was finally caught after he dozed off at an inn. Of course, given his love of women and ale, it's not surprising he finally got caught while being under the influence. Who knows, maybe one of his previously beaten ladies grassed him up – he surely deserved their wrath.
Thrown into Bedford Town gaol, Henry awaited trial and yet again tried to escape. He even managed to smuggle in a pistol. But finally, despite all his best efforts and sweet-talking at the Old Bailey trial in 1746, Henry was sentenced to death and transferred to Newgate prison.
But that wasn't quite the end of Henry's story.
The Ordinary at Newgate Prison (aka the chaplain) was required to speak to condemned prisoners every day for the weeks between the conviction and execution. They chronicled the confessions and behaviours of both men and women who were doomed to die. Their main focus was generally on the personal history of each criminal, their crimes, and questions of faith.
In 1747, the Newgate Ordinary recorded the story of a love affair between Mary Allen, a shoplifter sentenced to death, and Henry Simms. Mary was a shoplifter to the extreme, and according to records, she had gathered together a large quantity of goods sufficient to furnish a shop; maybe that was her intention.
During her confinement she contracted a great fondness for Gentleman Harry, which lasted to the Gallows; Just before they were turn'd off, Simms and Allen saluted each other; and then joyning Hands, went off, taking hold of each other.
Before his execution, Henry Simms wrote 'Hanging no Dishonour' in which he stated:
If I robbed the publick, I did it openly, and risked my life for every trifle I became master of.
Gentleman Harry didn't regret his sins, nor did he ask forgiveness for them. Instead, he saw himself as having the courage to pick a pocket or take a purse on the road and was willing to pay for his follies with his life.
He concluded his long letter with:
I am contented, now that I am going to die, to gain the character of a little sneaking sinner, and confess myself by many degrees honester than most of you.
Henry was hanged at Tyburn Tree in 1747 for stealing an old silver watch from Mr Francis Sleep of Dunstable, which you couldn't make up given the fact that Gentleman Harry was caught while sleeping.
Next week we take a brief break from the darker side of life and look at something a little more warm and fuzzy – The Chocolate House. Don't worry though, normal villainous service resumes the week after with Dick Turpin!
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The website is still a work in progress as everything is checked against the primary sources (as far as possible) rather than relying on Google, so thank you for sticking with me.
Henry Simms Commonly Called 'Gentle-Man Harry,' Highwayman." The New Newgate Calendar, vol. I, no. 12, 1864, p. 
Thompson, G. The Lives of notorious and daring highwaymen, and robbers, London: J. S. Pratt, 1843 p.215
Thompson, G. The Lives of notorious and daring highwaymen, and robbers, London: J. S. Pratt, 1843 p.321
Taylor, John. The ordinary of Newgate's account of the behaviour, confession, & dying words of the five malefactors who were executed at Tyburn on Wednesday the 17th of June, 1747. being the second execution in the mayoralty of the Right Honourable William Benn, Esq; Lord-Mayor of the City of London 
Simms, Henry. Eighteenth Century Collections Online. London: Printed for Henry Roberts; and Sold by the Sellers of London and Westminster, 1747.
Henry Simms Commonly Called 'Gentle-Man Harry,' Highwayman." The New Newgate Calendar, vol. I, no. 12, 1864, p. 
Simms, Henry. Hanging no dishonour. Being a modest attempt to prove that such persons as have the honour to make their exit at the Tripple-Tree are not always the greatest villains in the nation. In a letter from Gentleman Harry, Now under Sentence of Death in Newgate. Address'd to villains of all denominations in Great Britain. Printed for Henry Roberts; and sold by the booksellers of London and Westminster, [1747?]. Eighteenth Century Collections Online
Robert B. Shoemaker (2006) The Street Robber and the Gentleman Highwayman: Changing Representations and Perceptions of Robbery in London, 1690–1800, Cultural and Social History, 3:4, 381-405,
The proceedings on the King's commissions of the peace, and oyer and terminer, held for the city of London, and county of Middlesex, at Justice-Hall in the Old-Baily, on Friday December 5, Saturday 6, Monday 8, and Tuesday 9. In the 20th Year of His Majesty's Reign. Being the First sessions in the Mayoralty of the Right Honourable William Benn, Esq; Lord-Mayor of the City of London. Number I. Great Britain. Sessions (City of London and County of Middlesex) -47 J. Hinton, at the King's-Arms in St Paul's Church-Yard (London)
McKenzie, Andrea. "The Real Macheath: Social Satire, Appropriation, and Eighteenth-Century Criminal Biography." Huntington Library Quarterly, vol. 69, no. 4, 2006, pp. 581–605.
Gosee, P. The International Director of Pirates, Buccaneers, and Other Rogues, Fireship Press, 2008
Whibley, Charles. A Book of Scoundrels. London: W. Heinemann, 1897. This can be downloaded for free here (http://public-library.uk/ebooks/09/44.pdf) and is great fun to read.
Villette, John. The Annals of Newgate [electronic Resource] : Or, Malefactors Register. Containing a Particular and Circumstantial Account of the Lives, Transactions, and Trials of the Most Notorious Malefactors, Who Have Suffered an Ignominious Death for Their Offences, Viz. for Parricide, Murder, Treason, Robbery, Burglary, Piracy, Coining, Forgery, and Rapes: From the Commitment of the Celebrated John Sheppard, to the Acquittal of the Equally Celebrated Margaret Caroline Rudd. Including a Period of Fifty Years and Upwards, Both in Town and Country. Calculated To Expose the Deformity of Vice, the Infamy and Punishments Naturally Attending Those Who Deviate from the Paths of Virtue; and Intended as a Beacon to Warn the Rising Generation against the Temptations, the Allurements, and the Dangers of Bad Company. The Former Part Extracted from Records; and the Histories and Transactions of the Modern Convicts, Communicated by the Unhappy Sufferers Themselves, since the Author Has Been Appointed to His Present Office. By the Rev. Mr. Villette, Ordinary of Newgate, and Others. London: Printed for J. Wenman, No. 144, Fleet-Street, and Sold by All Other sellers, 1776.