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People keep saying "it couldn't happen to a nicer person" when it literally wouldn't happen to a nicer person

“It couldn’t have happened to a nicer person” and other variations are usually used in a facetious manner. Basically, it’s sarcasm.

The people using this turn of phrase are effectively saying “good, he deserves it for being a bad person”.

Yes, the comment here is noting the irony of how those words apply differently here.

yes, I'm a native english speaker, I was pointing out exactly that