THE ADVOCATE 461
VOL. 76 PART 3 MAY 2018
By Connor Bildfell*
THE ZONE OF DEATH†
Have you ever stopped to think about where the word “loophole” comes
from? The term traces back to medieval times, sometime around the 12th
century.1 In Middle English, the word “loupe” was used to describe the
narrow slits in castle walls that permit archers from the inside to rain their
arrows down on fast-approaching intruders from a position of safety. With
the passage of time, these “loupes” eventually became known as “loopholes”.
To this day, as noted in the Random House English Dictionary, the word
continues to denote “a small or narrow opening, as in a wall, for looking
through, for admitting light and air, or, particularly in a fortification, for the
discharge of missiles against an enemy outside”.2
There is also a connection with the Middle Dutch word “lupen” meaning
“to watch or to peer”. (Derived from the same word, the specialized magnifying
glass jewellers use to examine fine jewellery is called a “loupe”.)
“Lupenhole” was thus a window through which to peer.
The word “loophole” would later pick up an additional meaning. Beginning
in the mid-17th century, for reasons that are not immediately apparent
to this author, the word took on the figurative sense of being an “outlet” or
“means of escape”.3 This sense of “loophole” as a means of evasion or escape
is also recognized in the Random House English Dictionary: “a means of
escape or evasion; a means of opportunity of evading a rule, law, etc.”
Black’s Law Dictionary similarly highlights this figurative sense of the term,
as employed in the legal context—it defines “loophole” as “an ambiguity,
* Connor Bildfell is the Advocate’s copy editor and a lawyer at McCarthy Tétrault.
† This anecdote is adapted from a paper on “legal loopholes” that the author helped Madam Justice Saunders prepare for
the Vancouver Twenty Club.