The verb enjoin has 2 meanings, and these 2 meanings are nearly exactly opposite.
Also, the verb sanction. 2 meanings that are not just divergent but their own converse.
And, these two words, enjoin and sanction, are nearly synonymous at all 4 of their meanings.
One of the most anticipated moments of my week is every friday listening to Michael Barbaro pronounce the name of a member of his production team, Sindhu Gnanasambandan.