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Is there any example in history of something coming to mean its opposite?
Quite a few. The most recent well-known one is people often now using 'literally' to mean 'figuratively,' but there are other examples-
A quantum leap is often used to emphasize a large step forward, however in physics it means the smallest possible change of state.
And this isn't quite a contronym, but "silly" originally meant "blessed."
“Silly goes the other direction,” Curzan explains. “Silly goes all the way back to Old English, when silly meant happy or blessed.” This positive term quickly changed. Silly became a synonym for innocent or harmless, and then became an adjective for something or someone worthy of sympathy.
Something we feel sympathy for is something that’s weak. And something that’s weak is unsophisticated. Finally, silly went on to mean ignorant and lacking sense.
https://www.michiganpublic.org/arts-culture/2013-10-27/the-changing-meanings-of-nice-and-silly
And, as that same article said, "nice" used to mean what silly means today.
And thanks to internet culture blessed now can mean something similar to silly.
That's nice, dear.
I'm generally a nice person. Not very silly though.
Yeah I can relate.
Also, the American Fascist Party is still officially called the Republican Party even though it wants to change the government form to theocratic fascism 🤷
Swastika is a good example.
Oh yeah! Its funny, you can go to 19th century monuments in the US with swastikas carved into the stone.