Heads we win, tails you lose.

Dear Word Detective: I’ve been using the word “loophole” for as long as I can remember, but never thought much about the word. The “hole” part of it makes sense, since a loophole is a way to wriggle through some barrier. But what about the “loop” part of it? That suggests going in a circle, or perhaps ensnaring something, which doesn’t seem to fit with the way we use the word today. — Dave Anderson.

“Yesterday upon the stair, I met a man who wasn’t there, He wasn’t there again today, Oh, how I wish he’d go away.” When I first heard that ditty (written by William Hughes Mearns in 1899) as a child, I took it for just a tiny ghost story. I didn’t realize until I fell into the habit of voting that it was also a piercing insight into the modern legislative process. Bear with me here. You know how, when an important bill is passed in the US Congress, the TV news invariably focuses on the physical size of the result? “Twenty-three thousand pages long!” and so on. And it’s true that the mind-bending level of detail in these things has singlehandedly kept the adjective “byzantine” in our popular vocabulary. But much of the effort put into such bills has actually gone to keep things out: to enumerate, via deliberately convoluted conditional clauses, the times, people and places to which or when or whom those 23,000 pages do not apply. Just as in making Swiss cheese, the holes — the loopholes — are the most important part, and the man who isn’t there is running the show.

That concludes today’s meeting of the Society for Excessive Cynicism. Don’t forget to reclaim your cudgels at the door.

Considering how much time our legislators spend chasing their own tails, it does seem as if the “loop” in “loophole” must have something to do with the sort of “loop” that circles back on itself. But “loophole,” which first appeared in print in English in the late 16th century, involves an entirely different “loop.”

Today we use “loophole” to mean “a means of escape, especially an ambiguity, omission or hidden provision in a contract, law, etc., that permits evasion of its intent.” But the original “loophole” was invented in the age of knights and castles. Back in the 14th century, the “loop” in “loophole” meant “an opening in a wall through which to peer or launch a missile (e.g., arrow or spear),” and was probably derived from the Middle Dutch “lupen,” meaning “to lie in wait, to watch or peer.” A “loophole” was thus a narrow opening in the wall of a castle or other fortified structure which allowed archers, for instance, to fire at attackers while minimizing their own chances of being hit. “Loopholes” also provided light and ventilation in chronically dank castles and other buildings.

Such “loopholes” were, in many cases, just large enough to also provide a means of quick and surreptitious escape should the need arise, and here we see the glimmer of the modern figurative “escape clause” sense of “loophole.” But lest we think that such slippery morality is a recent invention, it’s worth noting that the first printed citation for this use in the Oxford English Dictionary is from way back in 1663 (“It would be much below You and Me, … to have such loop-holes in Our souls, and to … squeeze Our selves through our own words,” Andrew Marvell).

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