The Duke Who Paid The Headsman In Advance

On the morning of 15 July 1685, James Scott, Duke of Monmouth — illegitimate son of King Charles II — was led to the scaffold on Tower Hill for high treason after his failed rebellion against his uncle, King James II. He was thirty‑six.

Monmouth knew the reputation of the man who would kill him. Two years earlier, in 1683, Jack Ketch, the public executioner of London, had botched the beheading of Lord William Russell, needing several blows of the axe to sever the head and horrifying spectators.

Before kneeling, Monmouth approached Ketch and handed him money — reports say six or more guineas — saying: “Here are six guineas for you. Do not hack me as you did my Lord Russell, for I have heard you struck him three or four times.” He then ran his thumb along the axe blade and remarked that it was not sharp enough. Ketch assured him it would serve.

Monmouth knelt by the block but did not settle in the usual way; he placed his neck on it and then lifted his head slightly to adjust. Ketch took this movement as his signal and swung before Monmouth had fully braced himself.

The Horror

The first blow cut into Monmouth’s neck but did not sever it. According to eyewitnesses, the duke lifted his head and looked back at Ketch. The second blow bit deeper but still failed to detach the head. Monmouth was still alive.

Ketch struck a third time. The neck remained attached. A fourth blow followed, still not completing the job. Only on the fifth stroke did the head finally come most of the way off — and even then, some flesh and sinew connected it to the body. Ketch had to put down the axe, take up a knife and saw through the remaining tissue to finish the decapitation.

The crowd, thousands strong, had come expecting a swift, solemn beheading. Faced instead with a prolonged, bloody spectacle, they erupted in fury. Contemporary reports describe people surging toward the scaffold, shouting for Ketch’s blood. The sheriffs and guards had to form a protective cordon around the executioner and hustle him away to prevent the mob from tearing him apart on the spot.

One chronicler called it “the most butcherly execution that ever was seen.”

When the horror had subsided and Monmouth’s body was prepared, officials realised that there was no official painted likeness of him. He was the charismatic focus of a rebellion, a royal bastard who had led men in battle, yet no artist had captured him in life.

To remedy this, they had his head sewn back onto his body, dressed him, and posed him so that a painter could take his likeness. The only known portrait of Monmouth appears to have been painted post‑mortem, with his head reattached; some art historians note the unusually high collar, which may conceal the seam.

The Modern Relic

Jack Ketch’s name outlived him. Within years, “Jack Ketch” was being used in pamphlets and ballads as a generic term for the hangman or headsman; by the 18th century it had become a stock name for any executioner in English popular culture. Traditional Punch and Judy puppet shows include a character called “Jack Ketch,” representing the hangman who tries — and fails — to bring Punch to justice, often brandishing a noose or an axe for comic effect. The real man’s botched beheadings became children’s theatre.

Tower Hill, where Monmouth died under five blows and a knife, is now a public garden and memorial area beside the Tower of London. A plaque lists those executed there over the centuries; the Duke of Monmouth’s name appears among them. Jack Ketch’s does not.

Monmouth’s posthumous portrait hangs in galleries as the face of a doomed rebel. Ketch survives as a byword — a name you can still meet in puppet booths and old texts whenever someone needs to personify the executioner. One man’s neck turned another man’s incompetence into a permanent entry in the language.

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