"Don't picka da punk" is supposed to mimic the way an immigrant Italian would say, "Don't pick the pumpkins" (thus the connection to squash). "Squash" is a generic term for vine-grown vegetables (gourds, actually), including the zucchini (also known as courgette or marrow), and one of the most popular varieties of squash is the pumpkin. Thus, a county named "squash county", is probably famed for its squash crops. The "don't picka da punk" phrase, would suggest that this county is inhabited by immigrants who, in a stereotypical bigotted fashion, are supposed to be unable to speak (or write!) proper English. Thus, instead of "do not pick the pumpkins", they would write "don't picka da punk".
On the Disney comics Mailing List, Dan Shane wrote: "Living in Kentucky (not far from Don Rosa, as it happens), I've grown up used to hearing "pumpkin" incorrectly pronounced (and sometimes spelled!) as "punkin". So the joke as I read it means don't pick a pumpkin in a county that's bound to be full of them. I think it's a clever play on words, but only for those used to local dialectically-induced misspellings."
Christopher E. Barat wrote: "Supposedly, in the early days of heavy Italian immigration to the United States (around the turn of the 20th century, I believe), a number of Italians who settled in the large cities worked as fruit and vegetable salesmen, flower salesmen, popcorn and peanut vendors, and other kinds of "street vendors." The ethnic jokes and cartoons of the time habitually gave such people "Italian" clothes, fancy mustaches, and/or stereotyped "Italian" accents. Barks, Floyd Gottfredson, and Al Taliaferro all made use of such characters: for example, Gottfredson did so in the daily strip story "Oscar the Ostrich," while Barks did so in "Too Many Pets" (OS 29-03). Like black shoeshiners and Chinese laundrymen, Italian fruit and vegetable salesmen were one of the standard ethnic stereotypes of American popular culture for a good many years."
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