Q: I saw this headline in the Orlando Sentinel the other day: “Time for Florida to close the Internet sales-tax loophole.” That got me to thinking. Why is a way to evade taxes called a “loophole”?
A: In the 1300s a “loupe,” later called a “loop hole,” was a small vertical slit in a castle wall for spotting enemies and shooting arrows at them.
The earliest published reference in the Oxford English Dictionary is from William Langland’s narrative poem Piers Plowman, written in the second half of the 14th century.
Here’s the citation in Middle English: “Eche chyne stoppe, þat no light leope yn at louer ne at loupe.” (Translation: “Let chain close every chink, so no light leaps in at louver or loophole.”
The word “loupe” probably came from a Middle Dutch word, lupen, meaning to lie in wait, watch, or peer, according to the OED.
The OED’s first citation for “loop hole” (later, “loop-hole” or “loophole”) is from William Garrard’s Art of Warre (1591): “That not one of the towne do so much as appeare at their defences or loop holes.”
In those days, an archer in a besieged town would shoot through a loophole in the defensive walls at the surrounding forces.
Today, of course, a loophole is usually an omission or ambiguity that gives you an opening to evade a legal provision.
This figurative sense of the word showed up in the 1600s, but we’ll cite an 1807 example from the writings of Thomas Jefferson:
“What loop-hole they will find in the case, when it comes to trial, we cannot foresee.”
And people have been taking aim at figurative loopholes ever since.
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