Oversight

n. supervisory responsibility (from OED)

or

n. the act of passing something over through negligence (also from the OED)

I was ready to close my small run of auto-antonyms when Jonathan Cane suggested this one.  It is a wonderful word with two vastly opposing meanings, but one that can almost always be understood by context.  It comes from result of forming a compound with a preposition.  These often can result in too perfectly reasonable but different meanings.

I’m not sure if this would be a pure contranym because the two phrases don’t necessarily oppose each other.  Someone in charge of oversight could easily make an oversight, but the two ideas clearly don’t suit up for the same team.

Interestingly enough, the two different meanings are relatively equal in age according to the O.E.D.  As early as 1413, people were using the phrase to mean supervision (which is the exact same word if you think of it).  By 1477, it was already used to mean something that was missed.

Oddly enough, oversight can also be used as a verb.  One can oversight something by being negligent.  It was used in the 1600s, but has still been used in the twenty-first century.

As for Jonathan Cane, when he is not reading my blog, he is training people to run.  Check out his website at Citycoach Multisport if you are looking for a coach or if you just want to hear about how he looks good in moose antlers.

Cleave

v. to part or divide by cutting asunder. (OED)

or.

v. to stick fast or to adhere (OED)

My friend, and a very talented musician, Sandra R.B. suggested this word as a possible auto-antonym, and it was one of two that I am readily familiar with.  I was at a wedding of a college roommate of mine in Vermont when I was first stumped by this.  Her wedding vows consisted of something akin to “to cleave on to you for the rest of my life.”  The phrase was quite jarring, considering that my only understanding of the word was the first definition above.  How could a word mean to rip asunder and to adhere together yet still have any meaning?  Never mind the fact that, as a noun, it also means an Irish basket.

This is a rare case of a true auto-antonym, as opposed to one that was formed from misuse.  The word is actually two different words, stemming from two different etymologies, that happen to be spelled and pronounced the same way and have meanings that contradict each other.

The two words are not necessarily identical in their other forms.  In both cases you can say that you cleaved something or cleaved to something, but other forms of the past tense exist that are more specific.  So the retired lumberjack clove wood and cleft wood, while the divorced couple clave each other.  Wood is cloven while a contract is cleaved to.  In the end, these two words at some point just became too close to each other, and could only be cloven when put into different tenses.

For the record, my Vermont roommate still cleaves to her husband.  They are building a beautiful inn, called the Snapdragon in Windsor, VT, and you can read about its progress here.  The also have a delicious looking eatery called the Windsor Station Pub.  If you are ever in Windsor, cleave to those locations.

P.S. Cleave is also a noun form of the word cleft. According to the OED, the first published use of the noun cleavage was in Time magazine’s August 1946 issue.  It was in reference to a trade term about the cut of an actress’s dress.

Auto-antonym

n. a word with multiple definitions, at least two of which directly contradict each other.

Simply put, one of the most fascinating things in the English language.  The same word, same spelling, same pronunciation, can mean the opposite of itself.  Mostly, this happens when a word has developed a new meaning over time.  Additionally, there are many words that seem like auto-antonyms if you use different prepositions with them, but I don’t think that really counts.  I’d love to give an example of one, but I’m going to hold off to give them their own entries.