Pylimitics

It’s tax-returnseason in the US, which means that people across the country have been eagerly searching for “loopholes.” And the regime, of course, is all about loopholes, like most grifters. A loophole is a detail in a rule or law or regulation that enables you to argue, with varying degrees of success, that the rule shouldn’t apply to you or your specific situation. 

In the US system, loopholes are often created on purpose. They’re why a given bill in Congress that seems like it ought to be relatively simple often turns out to be hundreds, or even thousands of pages long. It doesn’t take much paper to say “if you’re caught littering, the fine is $100.” What takes all the extra pages is listing all the companies and people that are allowed to litter specific sorts of refuse in particular ways. 

But more to the point, the “hole” part of “loophole” is pretty obvious; it’s a hole in a law letting behavior sneak through — but what kind of “loop” is involved? A clue is that “loophole” first appeared in English in the 1500s, based on a word “loop” from the 1300s. If you visited the 1300s you’d see castles, and a common feature of a castle is a narrow window in a wall or tower. Those windows had a couple of purposes. They provided some light and air inside the gloomy place. They were also used to peer out at enemies that might be gathering, and to shoot an arrow or a spear at them. The windows were originally called “loops”, from the Dutch word “lupen”, meaning to wait and watch. 

If you weren’t just visiting the 1300s but actually lived there, it’s a pretty good bet that unless you were part of the nobility (remember those paintings of Henry VIII), you didn’t get all that much to eat. You probably stayed thin enough to fit through those loops yourself, should you need to escape for some reason — maybe stealing a sandwich. Thus the “loops” came to be called “loop-holes”. By the 1600s the term was being used metaphorically as well: “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, 1663). After that the only further change was to go from “loop-hole” to today’s “loophole”. The hyphen probably slipped away through a convenient castle window.