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Evan Morris (The Word Detective) and Christine Ammer (Cool Cats, Top Dogs, and Other Beastly Expressions) are two wordsmiths who at least tried to formulate an answer. Their speculations:

 

(1) In 19th century America, jay was slang for a hick, a simpleton, a gullible person. In that case, naked as a jay would refer to a completely vulnerable person, not to a bird. And we have another vestige of that meaning: to jaywalk. This referred to country bumpkins wandering around gawking at tall buildings and paying no attention to traffic signals.

 

So it is sort of about Canadians? Is that why they named their baseball team the Bluejays?

Edited by ieatcrayonz
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