In late 1990 and early 1991, Harry Nilsson sent proposals to TV network executives outlining a movie idea of his called 500 Santas.
According to Alyn Shipton in Nilsson: The Life of a Singer-Songwriter, in Harry's script ...
[..] Two homeless men contrive to receive lavish Christmas gifts by sending what appear to be generous presents in stolen Tiffany’s bags to the presidents of Fortune 500 companies. They figure that such exalted businessmen simply send reciprocal presents to anyone who sends them something and the men could then split the proceeds between themselves and their homeless friends. Only Donald Trump sees through the ruse, but is so impressed by it as a business plan that he does not give their game away.
-- Nilsson: The Life of a Singer-Songwriter 
The film was never produced.
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