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Jack Sheppard, Thief, Highwayman & Escapologist

April 9, 2011
by the gentle author

On the morning of 4th September 1724, an inconsequential thief named Jack Sheppard was to be hung at Tyburn for stealing three rolls of cloth, two silver spoons and a silk handkerchief. But instead of the routine execution of another worthless felon, London awoke to the astonishing news that he had escaped from the death cell at Newgate.

With the revelation that this was the third prison break in months by the handsome boyish twenty-two year old Jack Sheppard, he flamed like a comet into the stratosphere of criminality – embodying the role of the charismatic desperado to such superlative effect that his colourful reputation for youthful defiance gleams in the popular imagination two centuries later.

In the Spring, he broke out through the roof of St Giles Roundhouse, tossing tiles at his guards. In the Summer, with his attractive companion Elizabeth Lyon, he climbed through a barred window twenty-five feet above the ground to escape from New Bridewell Prison, Clerkenwell. And now he had absconded from Newgate too, using a metal file smuggled in by Elizabeth and fleeing in one of her dresses as disguise. Sheppard was a popular sensation, and everyone was fascinated by the inexplicable mystery of his unique talent for escapology.

Spitalfields’ most notorious son, Jack Sheppard, was born in Whites Row on 4th March 1702 and christened the very next day at St Dunstan’s in Stepney, just in case his infant soul fled this earth as quickly as it arrived. Unexceptionally for his circumstances and his time, death surrounded him – named for an elder brother that died before his birth, he lost his father and his sister in infancy. When his mother could not feed him, she gave him to the workhouse in Bishopsgate at the age of six, from where he was indentured to a cane chair maker, until he died too. Eventually at fifteen years old, he was apprenticed to a carpenter in Covent Garden, following his father’s trade, but at age twenty he met Elizabeth Lyon, his partner in crime, at the Black Lion in Drury Lane, a public house frequented by criminals and the infamous Jonathan Wild, known as the “Thief-taker General.”

On 10th September 1724, Sheppard was rearrested after his break-out from Newgate and returned there to a high security cell in the Stone Castle, where he was handcuffed and fettered, then padlocked in shackles and chained down in a chamber that was barred and locked. Yet with apparent superhuman ability – inspiring the notion that the devil himself came to Sheppard’s assistance – he escaped again a month later and enjoyed a very public fortnight of liberty In London, eluding the authorities in disguise as a dandy and carousing flamboyantly with Elizabeth Lyon, until arrested by Jonathan Wild,  buying everyone drinks at midnight at a tavern in Clare Market, Lincoln’s Inn Fields. Back in Newgate – now the most celebrated criminal in history – hundreds daily paid four shillings to visit Sheppard in his cell, where he enjoyed a drinking match with Figg the prizefighter and Sir Henry Thornhill painted his execution portrait.

Two hundred thousand people turned out for Jack Sheppard’s hanging on 16th November, just two months since he came to prominence, and copies of his autobiography ghostwritten by Daniel Defoe were sold. Four years later, John Gay’s “The Beggar’s Opera,” with the character of Macheath modelled upon Sheppard and Peachum based upon his nemesis Jonathan Wild, premiered with spectacular success. Biographical pamphlets and dramas proliferated, with Henry Ainsworth’s bestseller of 1839 “Jack Sheppard” – for which George Cruikshank drew these pictures – outselling “Oliver Twist.” Taking my cue from William Makepeace Thackeray, who wrote that, “George Cruikshank really created the tale and Mr Ainsworth, as it were, merely put words to it,” I have published these masterly  illustrations here as the quintessential visual account of the life of Spitalfields’ greatest rogue.

And what was the secret of his multiple prison breaks?

There was no supernatural intervention. Sheppard had outstanding talent as a carpenter and builder, inherited from his father and grandfather who were both carpenters before him and developed during the six years of his apprenticeship. With great physical strength and a natural mastery of building materials, he possessed an intimate understanding of the means of construction of every type of lock, bar, window, floor, ceiling and wall – and, in addition to this, twenty-two year old Jack Sheppard had a burning appetite to wrestle whatever joy he could from his time of splendour in the Summer of 1724.

Mrs Sheppard refuses the adoption of her little son Jack

Jack Sheppard exhibits a vindinctive character.

Jack Sheppard committing the robbery in Willesden church.

Jack Sheppard gets drunk and orders his mother off.

Jack Sheppard’s escape from the cage at Willesden.

Mrs Sheppard expostulates with her son.

Jack Sheppard and Blueskin in Mr Wood’s bedroom.

Jack Sheppard in company with Elizabeth Lyon escapes from Clerkenwell Prison.

The audacity of Jack Sheppard.

Jack Sheppard visits his mother in Bedlam.

Jack Sheppard escaping from the condemned cell in Newgate.

The first escape.

Jack Sheppard tricking Shortbolt, the gaoler.

The second escape.

Jonathan Wild seizing Jack Sheppard at his mother’s grave in Willesden.

Jack Sheppard sits for his execution portrait in oils by Sir James Thornhill  – accompanied by  Figg the prizefighter (to Jack’s right), John Gay, the playwright (to Jacks’s left), while William Hogarth sketches him on the right.

Jack Sheppard’s irons knocked off in the stone hall in Newgate.

Jack Sheppard  of Spitalfields (Mezzotint after the Newgate portrait by Sir James Thornhill, 1724) – “Yes sir, I am The Sheppard, and all the gaolers in the town are my flocks, and I cannot stir into the country but they are at my heels baaing after me…”

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26 Responses leave one →
  1. April 9, 2011


    I particularly liked ‘The Baroque Cycle’ books by Neal Stephenson where the character Jack Shaftoe is loosely based on Jack Sheppard. They manage to vividly conjure up a sense of adventure in London and the wider world during this period, through the story of this scoundrel in particular…

    Great blog BTW

  2. April 9, 2011

    I love the Jack Sheppard and Jonathan Wild stories. I did a lot of research on them once for a children’s book I was writing. I always thought they’d make a brilliant subject for a film/TV series. When I googled to see whether anyone else had ever come up with the same idea (other than John Gay, of course), I was surprised to see that there was once a musical film called Where’s Jack? featuring Tommy Steele, based on the adventures of Jack Sheppard. I must admit, I have never seen it.

    Your blog is wonderful, by the way.

  3. Alan Gilbey permalink
    April 9, 2011

    ‘Where’s Jack?’ is a tonally quite an odd fim that feels a bit like an ‘Oliver!’ style musical but with all the songs taken out. Other times it’s quite gritty and true to the story, though I doubt Jack was as twinky as Tommy Steele.

  4. April 10, 2011

    I had not heard of Jack and his ‘exploits’ ’til now. Many thanks for a colorful narrative about this fascinating and rather nasty scoundrel.

  5. April 12, 2011

    Great introduction to Jack Sheppard, though there’s just so much more to tell! I was first introduced to his story on the “Georgian Underworld” series on Ch4 (I think?) a few years back, but really enjoyed reading “The Thieves Opera” by Lucy Moore, which is highly entertaining and also gives a great background on Jonathan Wild, too.

  6. len sheppard permalink
    April 15, 2011

    jack sheppard is an ancestor of mine i am having research done now to find out more

  7. Heather Potter permalink
    May 18, 2011

    Very interesting blog, one I shall be following from now on.

    I was first introduced to Jack Sheppard by old tales told by my late father. Some of them seemed too absurd to be true but were subsequently proven to be so. Have also done a lot of research into his character which included the fact that he was interred in St Martins in the Fields churchyard. His remains were exhumed and reburied somewhere in Camden but I have yet to find out where.

  8. Sara Waterson permalink
    August 5, 2011

    I wrote an article on Jack Sheppard for the sadly defunct Rare Book Review, from the point of view of Jack being the first media-created ‘mega-celebrity’. It’s a fascinating tale both in its own right and as a sociological phenomenon: all those eminent people fawning over a petty criminal just because he was fashionable and famous for a brief moment.

    By the way he was given so much liquor on his way down Oxford St in the tumbril that he was dead drunk by the time he reached the scaffold – not unusual in those times if you had enough ‘friends’

  9. Bev Nicholson Was Sheppard permalink
    August 17, 2011

    My uncle traced our family back and stopped at Jack we are a big family may be in some way you are connected to us?

  10. November 16, 2011

    ‘Jack Sheppard’ by W. H. Ainsworth was one of the earliest book I remember reading as a child. It made a great impression and the story has stayed with me.

  11. luke sheppard permalink
    December 17, 2011

    hi just wondering how did u start to trace your family history my grandad said that jack was out relative but i aint sure if he is mucking around any help would b great my sheppard family do come from london tho

  12. Diane Blackwell permalink
    February 14, 2012

    I have a friend called Dave Sheppard, who told me he was related to Jack. There are clearly a lot of his antecedents about!

    And btw, the blog is excellent. I know I’m a little late in catching on to it, but please keep it up! Many thanks.

  13. Daniel Sheppard permalink
    March 20, 2013

    Good website glad I stumbled upon it…

  14. Very Unfortunate permalink
    March 27, 2013

    The death penalty for petty death? How sad.

  15. jackie haines permalink
    April 2, 2013

    My Mothers maiden name was Sheppard, (Mildred)
    My Grandparents were Leonora and Thomas Sheppard, they lived in Hull and Goole (Yorkshire)
    I remember my Mother telling me that Jack Sheppard was a relative of hers.
    I had been told that the Sheppards came from Cork , Ireland.
    Has anyone made an Irish connection?
    I would love to hear from anyone who might shed some light on this ….

  16. Lance Hitler permalink
    September 9, 2013

    I am listening to audio book by Ainsworth titled “Rookwood” it’s terrific. It has a great storey of Dick Turpin, another glamorous Highwayman. Great feature on Mr Sheppard . Thank you.
    P.S. Jack Sheppard was my 3rd cousin trice removed.

  17. mark shepphard permalink
    November 28, 2013

    My grandad told me that we were related to jack sheppard my great grandad changed the spelling of our name so that were not known as part of such a well known highwayman not to sure of the story how do you go about looking the information up

  18. Ronald Chadwick permalink
    March 13, 2014

    My grandfather, Henry James Sheppard always insisted that he was a relative of Jack Sheppard, The Highwayman. We still have a Jack Sheppard in our family to this present day. Also it is believed that my grandfather was related to the Reverend Dick Sheppard who died in the 1930’s.

  19. Lisa Sheppard permalink
    September 1, 2014

    Where can we find his family tree?

  20. September 23, 2014

    We all seem to be related!
    Dick Sheppard was my grandads uncle.
    Jack Sheppard ran with the Culworth Gang, just up the road from me.
    He was always spoken about in a whisper since our family became farmers and lay preachers!
    Very proud to be related and will enjoy visiting his haunts
    Glad to see our family has flourished!

  21. roberta edwards permalink
    October 6, 2014

    My family are descendants of jack sheppard.
    Does anyone know how we can see his family tree?

  22. Stephen Sheppard permalink
    November 1, 2014

    Intriging history. Tracing Sheppard’s in Ireland, only one Jack, however plenty of James and John’s. Would appreciate any links.

  23. isabel sheppard permalink
    December 26, 2014

    jack sheppard is my great great great great great great great great great uncle looking through the comments there seems to be quite a lot of sheppards! and if any sheppards are reading this we are also related to king charles the 2nd!!

  24. Jon Greaves permalink
    April 7, 2015

    I have many Sheppards in my family that lived in and around the the Fleet Street, Clerkenwell area of London at least as far back as the early 1800’s. I have often wondered if I am related to Jack. Can anyone here help me to find out for sure?

  25. wendy howard permalink
    July 28, 2015

    Is he Springheeled Jack?

  26. Gina kerr permalink
    March 20, 2017

    Come on..all these Shepards related to Jack. Let’s get real. He did not have any children. So no o e is directly descended from him!! He had siblings, so may have indirect link only.
    He had quite a wasted life really…but I agree there is excitement in the prison breaks, and heroism.

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