Homeless despite Yale degree; mental illness? drug addiction? choice?

I used to buy breakfast for a homeless guy semi-regularly when I worked in New York. Sometimes he would offer to buy me breakfast. He was a very personable sort and easy to talk to. He had been on the streets 15 years. During that time he had spent 2 nights in homeless shelters. He said that as dangerous as sleeping on the subway or in parks and doorways was he felt much safer doing so than sleeping in the shelters. In those two nights in a shelter he witnessed a stabbing and multiple fist fights that broke out over theft and accusations of theft.

I try not to judge and think there but for the grace of God go I. My own opinion is that we are failing as a society. For whatever reason or reasons there will always be some who do chose to live a homeless existence but when we have homelessness in the numbers we do right now something is fundamentally wrong, something that goes far beyond personal choice.