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Okay, I'm not an expert, but you know what kind of sounds like an illegal lottery? (might not be...again, not an expert)

Donald Trump sending an email to his supporters telling them if they "chip in" donations to his campaign, they will be entered for a "chance" to win a ride on "Trump Force Two".

Maybe this is fine with campaign donations?? But entry with a price with no "no purchase necessary" option, a random chance selection, and a valuable (to his fans at least) "prize", is this allowed?