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Anne Boleyn was executed on May 19, 1536.

Displaying an act of "mercy", King Henry VIII dispatched a skilled executioner to perform the execution by sword rather than by axe or being burned at the stake.

The swordsman was dispatched from Calais, English occupied France at the time. Obviously, the swordsman would have to have been skilled with a flawless reputation to have been summoned by the King of England.

According to author and historian Dr. Eric Ives, the swordsman was very skilled.

her beheading by a first-class executioner — “an expert in the use of the heavy continental executioner’s sword which could cut the head off a prisoner who was kneeling upright, in place of the clumsier English axe needing the prisoner’s chin on the block.”

Anne Boleyn herself even mentioned the skill of the swordsman.

An excerpt from a letter to Thomas Cromwell from William Kingston on informing Anne Boleyn on the postponement of her execution:

And then she said "I heard say the executioner was very good, and I have a little neck," and put her hand about it laughing heartily.

Why was this particular executioner chosen?

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    @TylerDurden I am not requesting sources. I am politely asking that when answering the question and citing the source, that I would prefer it not be from Wikipedia. Are users not asked to cite sources for their answers? – steelersquirrel Sep 29 '15 at 0:10
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    The point is that questions are supposed to ask historical questions, not be requests for research assistance. In other words, a question that asks, "Who was the general with the most victories in the Revolutionary War" is a legitimate question. Asking "What evidence is there that General Cornwallis had the most victories in the Revolutionary War." is off topic. – Tyler Durden Sep 29 '15 at 0:27
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    @TylerDurden Research assistance? Really? I have just always wanted to know what was so special about this particular executioner. Where does it state in the help center that these questions cannot be asked and are deemed off topic? – steelersquirrel Sep 29 '15 at 0:42
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    I'm sorry, but I find it not really clear what you're looking for. What's special about the Calais swordsman is that (or so the conventional account goes) he was skilled and would, presumably, be able to minimise suffering with a clean execution. That' the qualification he (supposedly) possesses. But you already know this, and you've cited the historical evidence for it (the letter). What else are you looking for? Please clarify that, especially the title, which seems to be asking something else. – Semaphore Sep 29 '15 at 8:01
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    @setobot5000 Well, since this is a site dedicated to history, I was posting this question to inquire if anyone else happened to be more knowledgeable on the subject. Isn't that why users post on SE sites? – steelersquirrel Sep 30 '15 at 0:40
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The question breaks down into two parts: Why a swordsman instead of an axeman, and why the swordsman of Calais.

I now believe that the answer I posted earlier was only partially correct. This source offers a more likely answer, that "Henry did not care about Anne's feelings," and that he chose the sword as "the symbol of Camelot, of a rightful king."

On the other hand, Anne didn't seem to mind the substitution. According to the article"

"‘I heard say the executioner was very good and I have but a little neck,’ Anne said the day before her execution, and laughing, she put her hands round her throat. It was, at least, to be a quick death: her head fell with one blow, her eyes and lips still moving as it landed on the straw."

Original answer:

Anne Boleyn's PREFERENCE was for a "swordsman" rather than an "axeman." (This is different from my earlier, and now "retracted" statement that it was her request.) In the letter referenced in the question, the warden of the Tower of London reported that: "I have seen many men and also women executed, and that they have been in great sorrow, and to my knowledge this lady has much joy in death."

The initiative appears to have come from Henry VIII, who seemed to anticipated that the swordsman would provide a less painful, and hence "preferred" death (unless they had discussed this beforehand, perhaps in another context). If so, he is a better man than I have given him credit for.

That may be because she could then die kneeling upright, instead of with her head on the block.

The Calais swordsman was chosen as the "best in class."

Anne Boleyn was treated with more consideration than Mary Queen of Scots, who died with her head on the block, requiring TWO strokes of an axe, and also Catherine Howard, whom Henry also executed.

  • That Anne Boleyn made the request is a very surprising claim. Can you quote the passage in question? – Semaphore Oct 1 '15 at 14:23
  • @TomAu Wow. Interesting. I have studied the Tudor period for 15 years and have never heard this claim. Could you provide a direct link to this source? – steelersquirrel Oct 1 '15 at 14:33
  • @steelerfan: Here's a link to my source: amazon.com/Churchills-History-English-Speaking-Peoples-Arranged/… – Tom Au Oct 1 '15 at 14:40
  • @steelerfan There is no contemporary evidence that Anne Boleyn made any such request. In fact sources such as the Spanish Chronicle states that Henry VIII sent for the Calais swordsmen before Anne was even put on trial ("He had sent a week before to St. Omer for a headsman who could cut oft the head with a sword instead of an axe, and nine days after they sent he arrived. The Queen was then told to confess, as she must die the next day" - Anne was tried on the 15th of May and executed on the 19th). – Semaphore Oct 1 '15 at 14:48
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    @steelerfan: What little I've read on this subject I read in the 1970s (in Pittsburgh), and more recently, indicates that Anne had a preference for the sword. Not "joy" in the usual sense. But imagine the reaction of some who is told that s/he will be shot in the head (instant death) rather than in the stomach (a painful lingering death). – Tom Au Oct 2 '15 at 17:38
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I live in Belgium, the former Low countries! In my regions it was normal if you were from high birth that the decapitation was done by the sword without discussion, and if you were of lower birth than they performed it with an axe! I am surprised to read that this rule didn't stand in England and that for high birth it was normal to use an axe?

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    This doesn't really answer the question, but I think you're right that the difference is interesting. Could I persuade you to ask this as a question? – Mark C. Wallace Sep 23 '18 at 15:38
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    In England it was normal for the lower classes to be hung, or drawn and quartered, or on occasion even gibbeted. Only the upper classes were ever beheaded. Perhaps it's part of the distinction between a republic and a monarchy. – Pieter Geerkens Sep 23 '18 at 15:39
  • @Mark C. Wallace In The Low Countries we had a great variety of death sentences! Women were never send to the gallows or hanged because this was not descend! Their skirts could blow up and that was amoral! They had to deal with the very cruel sentence to by buried alive! Or to be burned at the stake, or to be drowned! The drowning could be performed in a barrel or in a river! – Martine Audenaert Sep 23 '18 at 20:16
  • @Mark C. Wallace I also know that the witch hunters in the Low Countries didn't use the false methods the used in England! I refer to the examination with the needle to find the devilsmark! In England they had a mechanism that could retract the needle so that the witch didn't feel anything and that the didn't bleed! – Martine Audenaert Sep 23 '18 at 20:22
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Cutting off a head in one blow is somewhat harder than it may sound; the main issues are that the vertebrae are hard bones and unless the executioner is skilled he could miss, hitting the head or back instead. If the executioner misses by even an inch things can get very messy.

In those days a class of professional executioners existed who used specialized swords designed for decapitation. An example is shown below:

enter image description here

This sword, from the Higgins Armory, is inscribed with a short encomium on justice on the obverse (the reverse is shown in the photo). When sharpened, such a sword will make a clean cut and due to its weight will go right through bone no problem.

The skill is in swinging it so that it hits exactly the right place.

If you have any doubts as to the difficulty of this, simply get a 3-foot long 2x4 and plant it end-wise into the ground. Then take a 1/2" steel rod and try to hit it solidly lengh-wise. You will soon see it takes quite a lot of practice to do such a thing consistently.

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    This is a fine description of what an executioner does and uses, but it does not answer the question asked. – CGCampbell Sep 29 '15 at 17:34
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    This only needs to be edited slightly to include these words: "to make the death swift and clean, and not prolonged and painful." – Thomas Myron Sep 29 '15 at 21:20
  • But why go all the way to Calais? That's the core of this question. – SRM Apr 5 '17 at 0:07
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    I don't know, but maybe the closest executioner with a lot of skill using a sword was in Calais. And if it was normal to use an ax in England the only English possession where swords were used for beheading would be Calais. – MAGolding Feb 27 '18 at 23:02
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Having visited the Tower of London last week where Anne was beheaded, the Yeoman giving our tour told how Anne's doctor wrote to Henry to say that Anne had a crippling and debilitating fear of beheading by axe (he joked it was the olden day equivalent of a "sick note") and that was why Henry sent for the swordsman.

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    I'm glad you visited the Tower but you can't take everything the Beefeaters say as historical fact. Quite why the swordsman needed to be summoned from Calais remains a mystery. I'm sure London had plenty of skilled swordsmen who could have performed the task. – TheMathemagician Apr 6 '17 at 12:25
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    @TheMathemagician, London had plenty of swordsmen who could have run her through, or disemboweled her, or otherwise killed her with a sword. It had far fewer who could have cut off her head with a single stroke. – Mark Oct 27 '17 at 19:43

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