Although I have seen homeless persons being issues in American cities (San Francisco has a huge problem, just for example), I was shocked with my first experience with homelessness in Montreal.
It was back in the 2002-2005 time frame, not exactly sure when. I naively believed Montreal was much safer than any American city. Therefore, I behaved accordingly.
It was a Saturday night during Jazz Festival. I was staying at the since closed Hyatt in the Complex Dejardins, which I think is now a Doubletree. I walked from there to the Club Downtown strip club. I am not sure exactly how long that walk is, but I am guessing it's over a mile. Anyway, I actually started out on Crescent Street, had dinner there and then went to the Club Downtown afterwards. At the time, which was over 20 years ago, it was a premium, high quality strip club. Reportedly some agencies recruited there, very aggressively, at that time.
I met a girl there I really liked and ended up spending hundreds and hundreds of dollars on her. Back then, the U.S. dollar fetched $1.50 Canadian. I would come up to Montreal with $2000 in cash, change it for $3000, and spend all of it on escorts and strippers.
I was admittedly in much better shape back then. It was an absolutely beautiful evening, and I said to myself as I left the strip club at around 2 am, "it's too nice an evening to call a taxi. Montreal is safe, and I am in good shape. I will walk back to the hotel." I should note, back then I always dressed well when I went out. I was wearing a collared shirt, a sports jacket and dress pants, and dress shoes.
This was a mistake. On my way back, I suddenly noticed movements in the shadows. People were lurking in entrances to buildings and behind concrete supports. I suddenly became aware of them, it seemed. I continued on with a little trepidation when all of a sudden a person was in front of me, blocking my path and in an aggressive or seemingly aggressive stance. This person seemed to come out of nowhere, as if they suddenly were beamed down from the USS Enterprise in Star Trek.
The person then lunged at me, but as he did so, I could see that although he was bigger than me, he was unsteady on his feet. I responded with a hard, two handed shove to his chest which sent him flying and losing his balance- which was much easier to do than it should have been, because he was high as a fucking kite. He wanted to, but was physically incapable of robbing me. His legs were jelly and he could barely stay on his feet.
I continued on at a hurried pace, and looking back I could see that my shove had, for the moment, completely discombobulated the intoxicated homeless aggressor.
I beat a hasty retreat to the Hyatt and never again walked around downtown after midnight after that night. Lesson learned.