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Surely he COULDN'T care less?

This is one of those colloquialisms that has become so commonplace that it actually becomes a part of the language rather than being incorrect.

Those of us who know better bristle and retain pedantry. Consider semi-annual and biannual. Grr.

Yes, when enough people do / say something wrong over and over again, it sometimes becomes normalised.

Wrong would imply a right, but most interpretations of what is "right" are fairly arbitrary and mostly have to do with social and cultural hierarchy.

Logically it's wrong. If you COULD care less then that means you do care to some level whereas most people mean you COULD NOT care less. Simple...