As part of his State of the Union Address last Tuesday, President Obama pitched middle-class tax breaks offset, in part, by closing certain tax loopholes that can benefit America’s wealthiest. I’m not fit to weigh in on tax policy (though you may want to learn the curious origin of the word tax), but I do want to weigh in on this word loophole.

If you’re like me, this metaphorical loophole brings to mind a literal hole formed out of a loop of string or some such material. You would indeed think the word is exactly that: a simple compound of loop and hole. It might be, but its etymology still proves to be pretty knotted.

"Loophole." Doodle by @andrescalo.
“Loophole.” Doodle by @andrescalo.


It’s the loop in loophole that throws us for a loop. For this loop, we actually need to consider two loops

The first loop is the one we are most familiar with, the one formed in needlework or a noose. Some thread this loop back to a Germanic root that gives English the word leap. Others–famously, Walter Skeat–have proposed a Celtic borrowing, citing the Gaelic lub, a “bend,” “loop,” and “winding,” as well as “to meander.” The Oxford English Dictionary dates this meaning of loop back to at least 1475. Given Celtic languages’ surprisingly limited impact on the English language, this would be an interesting borrowing indeed.

But English has a second and older loop, an “opening in a wall to look through, or to allow the passage of a missile.” This is attested in 1393, and by 1591, the OED cites loophole as such and naming the kind of narrow arrow slits we see in castles. Some suggest that this loop is from same word as we see in a loop of string. Others, however, go Dutch, aiming at the Middle Dutch lupen, variously glossed as “to lurk,” “to lie in wait,” “peer,” “watch,” or “look slyly.” Oxonian scholars also mention an Anglo-Latin loupa in the late 14th century, referring to a medieval loophole and of unknown origin.

By 1664, according to the OEDloophole takes on the figurative sense that ultimately yields today’s tax loophole:

An outlet or means of escape. Often applied to an ambiguity or omission in a statue, etc., which affords opportunity for evading its intention.

The OED adds that the usage may be influenced by the Dutch loopgat, joining loopen (“to run”) and gat (“way”). This loopen, however much it resembles the Middle Dutch lupen, doubles us back to that Germanic base giving us leap–and, possibly, loop. Now that’s an etymological loop-the-loop.


The origin of loophole may well live up to its name. Loop figures into a number of useful expressions. Loopy, as in crazy or drunk, is probably from loopy’s original sense of “full of loops.” Thrown for a loop, and its earlier variant, knock for a loop, may originate in the boxing ring near the turn of the 20th century, thanks to some sleuthing from Ben Zimmer and Jonathon Green. In the loop and out of the loop appears some 70 years later in aviation circles.  Aviators maneuver loop-the-loopsConey Island thrilled with its famous Loop-the-Loop. In late 1950s and early 60s, Hanna-Barbera produced the onetime, pun-loving “do-good wolf”:

Maybe we should put the well-meaning but much maligned canine in charge of the US tax policy–and, hell, gun control.

m ∫ r ∫


2 thoughts on “loophole

  1. The Welsh chronicler Elis Gruffydd (1490–1552) provides evidence of the word “lŵp” which the dictionary glosses as being borrowed from 16th century English for a ‘loophole’ and must’ve been from the early “opening in a wall” sense of the word ‘loop’.

    “[t]rwy lwwp ne ffenesdyr ar y porth ner paal.” (through a loop or window on the door or fence.) My very rough translation of 16th century Welsh.

    Liked by 1 person

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