It took me a second.
We had already passed each other going down the little side street in Lakeview, so, flanked by his two friends, he had turned around to ask me his question.
He was tall and built, white with a blonde ponytail. I doubt he would have tried that if he weren’t white — privilege even among the homeless.
He looked about 40, but living on the street seemed a hard life. I’ll guess early 30s. He wore a dusty flannel that hung loosely about him, dusty black jeans and dusty white tennis shoes.
He looked like an aging gutterpunk who had taken to the streets to live off the grid, man, and be, like, free but who was starting to realize he was just homeless.
He looked at me somewhat amusedly, waiting for the response.
I smiled back.
“Sir?” he had asked me in a genuine, sincere, genuflecting tone. “Can you spare $20 for a bag of marijuana?”
In a way, I found it clever. In a way, I found it funny.
In another way, I realized he wasn’t taking the whole being homeless thing very seriously, that there were people in greater need, people who couldn’t muster a clever opening because they were too hungry and cold and who knew they wouldn’t get a positive response because they weren’t affable white men in the 18-35 demographic.
$20 for a bag of marijuana. It was worth a chuckle, but I didn’t give him one, just a slideways smirk matching his.
“No,” I said. “But thanks for the honesty.”
He smiled and moved on. I didn’t mean what I said.
Even if he wasn’t being honest, if he would have secretly gone behind my back and used that $20 for food instead of kind bud, I didn’t appreciate it.
It was another hustle in a town of hustle, another bit of entitled “make” in the “city on the.” It was his way of asserting superiority, of showing the two friends flanking him that even as a beggar he was the coolest, funniest, cleverest beggar in town.
It bothered me the way any panhandler with a well-rehearsed, polished hustle bothers me. It bothers me that he had been able to perfect his pitch over weeks, months, years. A human being had been living on the street so long, he had gotten good at it.
I’m writing this in my nice warm bed, huddled in a quilt with a glass of iced tea at hand.
I wonder where he ended up sleeping tonight.
Talking to Michigan Avenue panhandlers about rain
The most effective hustle I’ve received
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