One of the Freakonomics books had an interesting chapter about how rich people seem to care less about being honest with small amounts of money. They interviewed a guy who delivered bagels to an office building and had an honour system where he'd just put up a sign saying "bagels $1" and then come collect the money later in the day, and he said that invariably it was the floors with the executive offices that took the most bagels without paying for them.

The authors posited that while it's possible that the reason the execs got where they are is because they're dishonest, it's also possible that as you get richer you start to lose sight of how important a dollar could be to some people, and you also get used to going to events where lots of things are provided free of charge anyway.

So to a poor person, taking a bagel without paying for it is a big deal, but to a rich person it might seem perfectly normal.

Not that that makes it OK for Eric Trump to take free lemonade, but it might help explain why someone like him wouldn't even think twice about doing it.