“One should aim not at being possible to understand, but at being impossible to misunderstand”*…
Here’s an ambiguous sentence for you: “Because of the agency’s oversight, the corporation’s behavior was sanctioned.” Does that mean, “Because the agency oversaw the company’s behavior, they imposed a penalty for some transgression,” or does it mean, “Because the agency was inattentive, they overlooked the misbehavior and gave it their approval by default”? We’ve stumbled into the looking-glass world of contronyms—words that are their own antonyms…
This phenomenon is called enantiosemy, enantionymy (enantio- means “opposite”), antilogy or autantonymy; an enantiosemic term is necessarily polysemic.
Contronyms, also known as auto-antonyms or autantonyms– or just as Janus words: “25 Words That Are Their Own Opposites.”
For a longer list, see “75 Contronyms.”
* Quintilian (Marcus Fabius Quintilianus)
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As we note that context is everything, we might recall that it was on this date (which is, by the way, Fibonacci Day) in 1644 that John Milton published Areopagitica; A speech of Mr. John Milton for the Liberty of Unlicenc’d Printing, to the Parlament of England. A prose polemic opposing licensing and censorship, it is among history’s most influential and impassioned philosophical defenses of the principle of a right to freedom of speech and expression. The full text is here.

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