Who is the most interesting homeless person you met over the years? (Other than yourself 
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Being homeless for 20 years I have met a wide range of interesting people, most of whom were not contemplatives, so not much community, and mostly people I wouldn't want to encounter in a dark corner late at night. Serving breakfast to the homeless population in Prescott for a number of years I got to know many of them quite closely, and most of them would have been kind to me.
Quite a high percentage of the homeless population suffers from one or more addictions, mostly they self medicate severe PTSD, due to profound hopelessness. The typical situation for a homeless person is they were laborers who partied too hard one night and got a DUI and served 3 months in jail, they get out and everything that they owned was thrown away by the landlord. If they were married, then their wife either left or had a new husband. If they had kids then DPS will garnish 100% of any paycheck they work hard for, so there is no point in working. So, they panhandle enough to get drunk enough to sleep under a bush for the night, and maybe freeze to death before the Salvation Army serves them breakfast. It is the cruelty of the world that they are the victims of and have succumbed to that cruelty.
Among the homeless population is also people who are hiding from some crime. About 10% of the homeless population are pedophiles who served a 5 year sentence and can no longer get gainful employment. I recall one young man had a girlfriend in high school, who was younger than he was, and they were having sex, and the girl's mother had him convicted of pedophilia when he turned 18, and he served 5 years in prison, when I got out, there was no work for him, no family to help him. The odd thing is he had lived in Prescott, and the mother of his high school girlfriend worked at the Salvation Army, so he saw her every morning for breakfast as Sally's. He had nothing to look forward to. It get weirder, The mother had grown up in the Salvation Army, because here parents worked for the Salvation Army serving the poor, and she had been abducted by a homeless man and gotten pregnant by him, and eventually recovered and brought back to her parents, and the girl this guy dated in high school was the product of that abduction. These are the kinds of stories that these homeless people come from.
Among the homeless population are a very small number of serial murderers who are on the lamb. They murder someone vulnerable, and move on to the next town to live in the homeless population. In Prescott I got to know 2 men who I have a lot of reasons to believe are serial murders, but without evidence there is nothing any of us can do. Upon my recent return to Prescott I found a homeless woman missing who had been in my opinion too friendly with one of these possibly sociopathic serial murders. I tried to warn her, but I could never find her alone without him right there. I reported her missing to the police along with my suspicion, and the man in question has not been seen for a few weeks, so I think he is on the lamb, and with no body, but a missing person report, he is free to disappear until her body is found. So, I have a number of suspected serial murders who I am sure would kill me if they ever found me alone in a hidden place.
However, I did meet a few interesting people who didn't seem to be career criminals. One such person was a native American man whom I met in Bolinas, CA. He was interested in hunting and foraging, so we had many conversations with our shared interest. He at one time had lived in San Francisco where he would kill sea gulls and sell them by the garbage bag full to local Asian restaurants where they would serve them as chicken on their daily menu.
More recently I met a guy who was a devotee of some Indian guru. He had worked as a EMT in the San Francisco bay area in the 70s. He was about my age. He traveled around the world living in dharma centers associated with this guru. He was from Phoenix and I met him in Prescott. He had some money that came to him monthly. He had bought a remote parcel of land and had built a refuge for himself. He is convinced that civilization will collapse any day now, and he has built his refuge to hide from the chaos. I would say he is the most interesting, and least criminal of the homeless people I have met.
I recall another interesting person I met in Bolinas, CA, who had built a boat using a framework of conduit with nylon mesh stretched over it, then he painted may layers of latex over the mesh to make it waterproof. His plan was to sail it up and down the California coast. The last time I saw him he had finished the boat and had headed out to sea.
