The Downtown Hustler

I had an encounter with a man in downtown Chicago on Saturday night. Most people from the suburbs or from out of town would probably describe him to their friends or co-workers as a homeless man. I suspect he was something that started with an “h”, but the word that came to me when I first saw him was “hustler.”

He emerged from the shadows on the south side of Jackson Boulevard as I was walking east toward Michigan Avenue. I had made my way over to the Federal Center, looking for a post office box, and was going back to my car, which was parked in the Grant Park South garage. I noticed him about mid-block between Wabash and Michigan. He was wearing dark clothes—dark green pants, a dark blue jacket, a dark gray knit cap.

I first saw him when he stepped off the curb, angling across Jackson toward the sidewalk on the north side of the street. I was the only other person walking on the street, and I knew immediately he was angling to intercept me. Rather than speeding up in an obvious attempt to get past him, I kept my stride. As it was, he hopped up on the curb just ahead of me. Then he turned and faced me as I walked by, but made no attempt to stop me.

“Got bless you,” he said.

“God bless you, too,” I replied.

“Do you have any change, anything at all?”

I knew I had nearly two dollars in change. As so often happens in these situations, my decision about what to do was made in an instant, and I didn’t hesitate. I stopped, dug into my pocket and pulled out what I had. “Here,” I said. “Be safe tonight.”

He examined the change, and closed his fist around it but didn’t immediately put it in his pocket. I turned and started walking again toward Michigan Avenue. Out of the corner of my eye, I saw him start, hesitate, and then begin to follow me. Then, unexpectedly, he called after me with a strange question. “Have you ever done anything bad?”

I slowed and half turned back. Even with his dark skin, I could see in the street light that his brow was furrowed, and his mouth was slightly open. It was an earnest look, and he expected an answer. “Sure,” I said. “Absolutely.”

I kept walking and was nearly to the corner when he called out again, “You’ve done bad things? Things you regret?” He paused. “I have and I don’t know what to do. That’s why I’m out here. I’ve made bad decisions in my life.”

I stopped and turned and looked him in the eyes. He was about 10 feet from me. “Of course I’ve done things I regret, things I wish I hadn’t done. I’ve hurt people. But those things don’t have to define you, man. You can stop doing them, you can try to fix them. Make your reaction to what you’ve done define you.”

With that I turned and started across Michigan Avenue against the light. There was no traffic coming and I thought at least I could get out on the traffic island. He didn’t say anything else. Halfway across the street, I turned and glanced over my shoulder to see where he was. He was walking slowly up Michigan Avenue, looking at the sidewalk.

Sadly, I had reached my limit of casual stranger conversation. On a better night, in a different mood I might have asked him if he wanted a cup of coffee, or something to eat. I sensed there was more he had to say, or maybe other questions, but I also believed that if I indulged him he would eventually ask for more money to catch a train or a bus or rent a room in an SRO because all the shelters were full. I just wanted to go home.

So I ditched this fellow and his strange but earnest questions. The whole encounter was odd. Maybe it was the fact it was just the two of us on that block at that moment, but looking back on it, the episode seemed almost like the end of an evening shared by two acquaintances. As one leaves, the other, emboldened by an understanding of friendship, asks an unexpected question that truly seeks an answer. With a short answer given, there is an inflection point, at which the conversation either continues or ends.

I ended it, but I wonder where it would have gone had we continued. Would it have degenerated into a panhandling hustle or was there some other reason he intercepted me on that sidewalk? Maybe he just wanted to talk and felt asking for money was the introduction he needed—the opposite of what most panhandlers do, which is engage in bullshit conversation first and then get down to the real business, which is asking for money.

This guy blessed me, asked me for change, looked at the change, and then asked me a question that, had it come from someone I knew, might have led to one of those conversations where you find a restaurant to sit at and talk, get kicked out of there when it closes and find a coffee place, get kicked out of there when it closes and then walk the streets until you realize the trains aren’t running any more and you have to find cabs.

Maybe he wasn’t a hustler at all; maybe he was just being human, and looking for someone to share that with. Instead maybe I was the hustler, hustling away.

Happy New Year.