A: We are often told that the expressions “the devil to pay” and “between the devil and the deep (blue) sea” do not refer to Satan but to a perfectly innocent nautical devil. This “devil” is a seam in a ship’s hull, on or below the waterline.

“The devil to pay” is supposed to be a short form of “the devil to pay and no pitch hot.” This interpretation depends on a homonym of the verb “pay,” which means “to apply pitch.”

Unfortunately for the nautical explanation, both expressions are attested much earlier than is the requisite sense of “devil.”

We first find “the devil to pay” in a poem written about 1500. The couplet, rendered in modern English, goes “It would be better to stay at home forever than to serve here to please – or pay – the devil.”

We have no evidence for the longer “the devil to pay and no pitch hot” until 1828.

“Between the devil and the deep sea” goes back at least to 1637. Robert Munro, in “His Expedition with the Worthy Scots Regiment called Mac-Keyes Regiment,” wrote, “I, with my partie, did lie on our poste, as betwixt the devill and the deep sea.”

The “devil” in a ship’s hull, on the other hand, is first reported in William Henry Smyth’s “Sailor’s Word-Book: An Alphabetical Digest of Nautical Terms,” compiled about 1865. It is true that nautical terms are likely to enjoy a long oral use without being written down. But three and a half – or even two – centuries seems rather too long to be an acceptable assumption for the nautical explanation. It is more likely that this proverbial “devil” is the Devil himself.

Q Where do we get the word “crack,” as in “a crack marksman”? Is it related to the word “crackerjack”? – G.M., Fairfield, Conn.

A: The adjective “crack,” defined in Merriam-Webster’s Collegiate Dictionary, Eleventh Edition, as “of superior excellence or ability,” first came into English in the late 1700s, long before “crackerjack” or “crackajack” arrived on the scene. (That word, a noun meaning “a person or thing of marked excellence,” was first seen in print a hundred years later.) The adjective “crack” is actually derived from a sense of the noun “crack.”

If asked to define the noun “crack,” most people would come up with such familiar meanings as “a fissure” or “a weakness or flaw.” The adjective derives instead from an old British slang use in which “crack” means “a thing or person of superior excellence or ability.” This sense is a play on the verb “crack up,” meaning “to praise.” We usually use this sense of “crack up” in negative constructions, as in “Riches aren’t everything they are cracked up to be.” (“Crack up,” in turn, is related to the use of the verb “crack” to mean “to say or utter” in contexts like “crack a joke.”)

This column was prepared by the editors of Merriam-Webster’s Collegiate Dictionary, Tenth Edition.

Readers may send questions to Merriam-Webster’s Wordwatch, P.O. Box 281, 47 Federal St., Springfield, MA 01102.


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