Where does the expression “the devil to pay” come from and What does it mean?

The expression “the devil to pay” means: Serious difficulty; great trouble or misfortune; perplexity; confusion; mishap. “There’ll be the devil to pay if I don’t get home in time for dinner.”

There are two schools of thought about the original meaning of this. One is that it related to witchcraft, to the selling of one’s soul to the devil and the payment exacted for its release.

This would seem to be the sense in the earliest quotation that we have, occurring under date of approximately 1400 in the poem, “Titivillus,” in the collection of ancient manuscripts, Reliquice Antiquce, “Beit wer be at tome for ay, Than her to serve the devil to pay.”

But “devil” is also a nautical term for the seam nearest the keel of a vessel, and “pay” means to calk.

Hence, among sailors “the devil to pay” could mean to calk the seam nearest the keel. This could be done, in former days, only when the vessel had been careened, tipped on its side.

Such an operation, between tides, would be difficult, especially so if the expanded form of the expression is considered, “the devil to pay and no pitch hot,” as we find it in Sir Walter Scott’s The Pirate (1821): “If they hurt but one hair of Cleveland’s head, there will be the devil to pay, and no pitch hot.”

Proof is lacking that the nautical was the original sense, but this is the logical source of the phrase.