"You could argue that he was smart enough to say things like that."
Agree. There is a pattern with people with money who do this. Oprah on her show would take people to her Chicago house which was nice but not opulent in the same way as her other houses. And she would make random statements about the cost of things to try and sound like an ordinary person. As if we are supposed to believe that someone worth hundreds of millions really needs to care about the price of vegetables in the super market? People try to wear frugality like a badge of courage trying to seem like "real" folk. I know of a particular wealthy VC who talks about flying coach. They are trying to say "I'm just like you.." don't be jealous.
While I've seen many wealthy people give away plenty of money to charities I have yet to see one (while still alive) that gives away all of their money except enough to live like an ordinary person in suburbia would do. Or even a majority of their money.
Trump of course has made a good living out of trying to say what a "shitload" of money he has. That's because that is what he is trying to sell an image of being successful which has of course helped him become successful. That's part of his product.