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Has there ever been a viable challenge to the constitutionality of the Hughes Amendment?
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There has not, as far as I can tell. Farmer v. Higgins is the closest thing, but the 11th Circuit evaded the Constitutional question and focused solely on the legislative intent. The Supreme Court declined to hear the appeal.
While it would be a good case to try, I think, it seems like one of those issues that would be better served once a solid judicial and legal foundation is established. That's what is going on now, I'd say, with the previous Chicago and DC cases, as well as with the current Chicago case and what will no doubt be a future California case.
I, too, believe that the Hughes Amendment was a pretty shady deal.