Who can forget (well, of course you can - there are thousands of these thing) when Trump gave a speech to the Boy Scout Jamboree. Aside from it being highly inappropriate to address them like it was one of his rallies, he told a story that started like this:
"And he went out and bought a big yacht, and he had a very interesting life. I won’t go any more than that, because you’re Boy Scouts so I’m not going to tell you what he did. Should I tell you? Should I tell you? You’re Boy Scouts, but you know life. You know life. So look at you. Who would think this is the Boy Scouts, right?
He so badly wanted it, he got bored with this life of yachts and sailing and all of the things he did in the south of France and other places. And in the end he failed, and he failed badly. Lost all of his money. I saw him at a cocktail party, and it was very sad because the hottest people in New York were at this party. "