Some words are easy to guess at as regards origins, others are a bit of a puzzle. This came to mind recently when someone used the word “loophole” in the context of a contract. We all know what a loophole is – a technicality that allows escape from a contract or a commitment – but how did the word originate? I figured that a loophole was obviously some sort of hole that had allowed escape but why "loop"?
One explanation sometimes offered is that it comes from the narrow slits in the walls of medieval castles that were used by archers and later musketeers. These narrow openings were called loopholes, the word “loop” being an obsolete word for “window”. The strategy behind such openings was that it was easy to launch arrows and projectiles from them without having similar objects coming back through the slits. It has been suggested that because the loophole could be used by children and small adults as a means of escape, the term came to be applied to a means of escaping a contract.
The more likely explanation is that the word comes from the Dutch word “loopen”, meaning “to run”, which is still reflected in the English words “lope” and “leap”. Another Dutch word “lupen”, meaning “to watch, peer”, is the likely origin of the castle loophole, the word “lupenhole” meaning window hole.
The word loophole in the sense of contractual loophole, allowing evasion, was firstr used by the poet Andrew Marvell in 1663.
In 1946 when W C Fields, on his deathbed, was observed to be reading the Bible, an observer commented that he that he had not shown any interest in that book previously. “Just looking for loopholes”, he replied.