19. 1956 Rolls-Royce Silver Cloud
Said to be one of the first cars he ever owned, Donald had Rolls-Royce build him a replica of his original 1956 model. While Trump was willing to shell out big bucks to have the company rebuild him one of these classics, reports claim the Silver Cloud does not bid high at auctions. It seems Trump was going with a more nostalgic feel when he made this purchase.