buybuydandavis comments on Be a little bit more trusting than most people think sensible - Less Wrong
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Interesting anecdotes in the article, but I think the guy missed a couple of points.
Part of why Mr. Moneybags was relaxed and secure was his money. He had power. He was likely fully insured for property damage, and fully assured of getting his way should it become a legal matter. Property damage is at worst an annoyance, while it is a bigger deal for people of lesser means.
On the other hand, I'd expect that trust elicits trustworthiness in the majority in those not habitually criminal or predatory. Sounds like something Kahneman would look into. Anyone have citations on this?