The deal with the Devil is a common trope. Also common is the notion that you had better check the terms extremely carefully, because the Devil is prone to slipping in tricks of wording to his advantage, or conversely that the human can trick the Devil through some clever wording. This can be called a "quibble". When applied to deals with the Devil, is this a medieval concept or something more 20th century?

What is the earliest example of a deal with the Devil in which the human, or the Devil, uses a trick of wording to their advantage?

What counts as a trick of wording: it would be some careful wording in the contract that one party initially thinks means X, but another party knows really means Y. And later the party who knew it means Y uses that fact to gain an advantage over the other party.

Deals with the Christian Devil or demons count. Deals with any other supernatural entity do not count.

For some background information, it is stated in the Wikipedia article about quibbles, that:

A pact with the Devil commonly contains clauses that allow the devil to quibble over what he grants, and equally commonly, the maker of the pact finds a quibble to escape the bargain.

This line references the sci-fi encyclopedia page about quibbles. However, on that page I do not actually find any examples of either the Devil or the human using a trick of wording to gain an advantage. On the sci-fi encyclopedia page titled "read the small print" one example is given, a story from 1951 called The Devil in Velvet. So it is at least as old as 1951; is it any older than 1951?

  • Are you asking about works based on the Christian concept of the devil or demons, or would something based on something like the Rakshasas (demons from Indian religions) count?
    – Laurel
    Commented Jan 18 at 2:27
  • @Laurel Christian Devil/demons. Although if there was something with Rakshasas or demons from other religions that would be very interesting.
    – causative
    Commented Jan 18 at 2:30
  • 1
    Very likely to be a trope older than dirt
    – Radhil
    Commented Jan 18 at 2:39
  • @Radhil I'll believe that when I see it.
    – causative
    Commented Jan 18 at 2:40
  • 1
    Is this a superset of scifi.stackexchange.com/questions/283070/…
    – Sam Azon
    Commented Jan 18 at 2:45

1 Answer 1


Jonathan Moulton

The American Revolutionary War Brigadier General, so this is late 18th century.

So the legend goes, Moulton agreed to sell his soul to the Devil in exchange for two boots full of gold. Ahh, but Jonathan was crafty. He cut holes in the floor as well as the bottom of his boots. No matter how much gold the Devil poured in, the boots would never fill up.

Moulton (allegedly) now had a basement full of gold and got to keep that precious soul all to himself.

In retaliation for the trick, the Devil burned down Jonathan’s house. He and his family barely escaped alive.

The oldest non-tricky deal was with God

Job 1:12

And the LORD said unto Satan, Behold, all that he hath is in thy power; only upon himself put not forth thine hand.

Both God and Satan stick to the deal, but God does allow a renegotiation, removing the restriction.

  • Jonathan Moulton definitely counts, but let me point out that the date that matters is when this legend about him began circulating or was published. Was that actually during his life or was it significantly afterwards? The story was published in John Greenleaf Whittier's "Home Ballads" in 1865. Possibly this particular story about the boots had circulated earlier, but also possible is that it's due to Whittier.
    – causative
    Commented Jan 18 at 15:04
  • Well, I found a claim it was in "Home Ballads," but here's the OCR text of Home Ballads and I don't see any mention of Moulton in it: quod.lib.umich.edu/m/moa/…
    – causative
    Commented Jan 18 at 15:23
  • On the topic of New England deals with the devil, here is a story from 1896 where a farmer tricks the devil into building a barn for free: newenglandfolklore.blogspot.com/2014/11/…
    – causative
    Commented Jan 18 at 15:28
  • The boots story at least appears in the Moulton Annals (1906). Most web pages that mention this story are frustratingly light on references.
    – causative
    Commented Jan 18 at 15:41
  • If anyone has access to Icelandic folklore, Sæmundr Sigfússon (1056-1133) is renowned for tricking the Devil or his minions this way on several occasions. Commented Jan 18 at 17:10

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