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There's a lot of speculation about that phrase online, but no definitive etymology I could find. I have heard the vulgar equivalent "jack shit" as well as simply "jack" both with the same meaning.
It seems to have been derived from the phrase "doodly squat" and later "diddly squat", again with the same meaning.
Part of the problem with deducing the etymology is that the word "jack" has so many unrelated meanings. Sorry I couldn't be of more help.
IMO jack squat and diddley squat don't mean nothing but rather nothing of value. When Meathead is expounding on some wacko liberal theory, Archie is likely to declare that his son-in-law doesn't know jack squat about the subject. It's not that Meathead is saying nothing, it's that he's spewing garbage, since he doesn't know sic 'em.
Doing jack squat doesn't necessarily mean you did nothing, either. Maybe you looked through your coin jar in search for wheat cents, or you got a joint out of the freezer to thaw for tomorrow's roast, or you wqashed the supper dishes, but the sink is full of dishes from breakfast and dinner. What you feel is a lack of accomplishment.
What do you squat for? To defecate. And you'll find that shit is a less delicate way to say the same thing. He don't know shit about it, and he didn't do shit once he drug himself out of bed. I used to have a girlfriend who used sugar as a euphemism for shit. I used to think it cute when she'd say, "Oh, sugar! Forgot to fill up the tank" or some such, until I realized that she used sugar as an endearment for me. "What are you up to, sugar?" The relationship went downhill rapidly once I picked up on that.
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