Inside the topsy-turvy world of contronyms
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.
1. Sanction (via French, from Latin sanctio(n-), from sancire 'ratify,') can mean "give official permission or approval for (an action)" or conversely, "impose a penalty on."
2. Oversight is the noun form of two verbs with contrary meanings, "oversee" and "overlook." "Oversee," from Old English ofersēon "look at from above," means "supervise" (medieval Latin for the same thing: super- "over" + videre "to see.") "Overlook" usually means the opposite: "to fail to see or observe; to pass over without noticing; to disregard, ignore."
3. Left can mean either remaining or departed. If the gentlemen have withdrawn to the drawing room for after-dinner cigars, who's left? (The gentlemen have left and the ladies are left.)