A story from my former career: the cigarette scrounger and slick suit guy

I live near a gentrified little city in New England.
I came here 27 years ago, the recipient of a private scholarship to an expensive college.
At the time I liked it very much here, so stuck around. It was less gentrified back then.

But the colorful teens and twenty somethings enlivening the little downtown dispersed as rental rates climbed,
and the variety and distinctness of the shops diminished. There has been a very visible homeless population
as long as I've been here, and it has only increased over the years. Putting on my sardonic humor hat,
at least there are more alcoves for them to shelter in as more shops close.

How I came to this point would be a big digression, but
about 15 years ago I embarked on a career as a street musician.
It was often difficult and grueling, and I burned out on it,
but for a little while it barely covered my necessities,
and it gave me a lot of experiences.

During my time working the street downtown I became familiar with this man who I'd see
scrounging the sidewalk for any cigarette butt with a bit of "meat" left on it. He hardly spoke,
but we got familiar enough to greet each other with a glance or a nod now and then.
I probably gave him several cigarettes over the years. His clothes were filthy and shabby.
I remember how happy I got that day I saw him showered and clean in some new clothes
and how his spirits seemed so lifted by it.

One slow day I was starting to feel like I was wasting my time and energy out there,
when an immaculately well dressed young man walking down the sidewalk stops by me,
pulls out a packed money clip with a $100 on top, looks at it, digs in his pocket again to find
two quarters to tip me with. A maddeningly exasperating experience.
Almost frustrating enough to pack it in for the day,
but I stuck it out for a few more minutes because I can get stupidly stubborn sometimes.

A couple minutes after slick suit guy is gone, the cigarette scrounger comes along.
He stops and digs in his pocket. This is unusual, he's never done this before.
He pulls out the most dilapidated dollar bill I've ever seen.
It had just enough structural integrity to be usable.
He puts it in my all but empty tip jar.
I'm in shock.
I want to tell him to keep his dollar.
But this feels like a gift of the highest order
and I don't want to offend him.
He mumbled something unintelligible and shambled off.

"I'm fucking done."
And I packed up and went home feeling very discombobulated