There has been some discussion on twitter of words that "reliably mean their opposites." Some suggestions:
"fine" particularly when given as a one word answer
transparent (with reference to government or corporate behavior)
Tyler Cowen asked if there is a word for these. There are some linguistic terms for words with two opposite meanings: antagonym, contranym. But that isn't the same as a word that people generally use ironically.
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I think this all just falls under the category of sarcasm.
None of these words actually mean their own opposites - they just sometimes get used sarcastically to convey the opposite meanings. It's just idiomatic speech whose intention is conveyed more by tone and context than by word choice.
The only English word I know of which is actually, by definition, its own opposite is "cleave". You can cleave things together, and you can also cleave them apart.
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