#32: The Cleverest Hobo

July 11th, 2012

This is the tale of the smartest bum I ever met.

Since I don’t give Stanford-Binets to every panhandler who’s crossed my path in the City That Mostly Works, I just think he was the smartest bum I ever met, just like I think it was in Old Town, I think it was 2009 and I think it was one of those clear, hot summer days with that tang of humidity that just makes everything irresistible.

And by “bum,” I don’t mean “homeless person.” This guy was a bum. You’ll soon see.

I was on a sweat-laden bike ride when I saw a store and decided I needed peanuts.

Outside the store was the world’s cleverest hobo. I didn’t know it at the time, but there he was: not smiling, not talking, just looking forward and holding up a StreetWise. I was in a good mood, so I said I would get him on the way out. He didn’t say a word, just sort of grumbleshrug looked away. That’s the important bit.

The store was an organic, healthy, artsy-fartsy sort of place, so I ended up spending too much time looking at cruelty-free wines and cheeses I probably shouldn’t be buying. So I bought my peanuts and clutched two one-dollar bills from the change to purchase the rarest commodity of all — liberal righteousness.

I did not plan to buy the StreetWise (which, for the uninitiated, is a Chicago magazine/social service group notable for giving homeless people gainful work as magazine street vendors). I, like most people who “buy” StreetWise, planned to give the vendor my money and then say in a loud voice, “No, keep the magazine.” Then I get thanks from the vendor for allowing him to sell the magazine at least twice (probably more — lots of liberals on the North Side).

I handed the man the $2 and waited to decline his offer.

Then, nothing. He just took my money, put it in his pocket and looked away.

I looked at him. I looked at the pocket holding my $2. I looked at the StreetWise he was holding out. And then I looked at his neck, which was notably absent of the ID lanyard all official StreetWise vendors wear. The dude was just a bum with a StreetWise.

I was peeved. I was pissed. The two bucks was nothing — I should report this jackass for taking advantage of a good organization helping people in his situation.

Then it hit me.

Remember how I said him not saying a word was the important bit? He had never claimed to be a licensed StreetWise vendor. He never claimed to be anything other than a guy who holds magazines weird. I couldn’t do a damn thing.

“No, officer. I was just sitting here sunning my magazine when this guy hands me two dollars and just stares at me. He said he wants my magazine? Wait, he wants me to offer him my magazine so he can tell me to keep my magazine? And then he called the cops to report me for holding my magazine misleadingly? Yes, officer, I will press charges. Can’t be too safe — lots of weirdos in this town.”

I moved on, leaving my money with the cleverest hobo. He sort of earned it.

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You are currently reading #32: The Cleverest Hobo by Paul Dailing at 1,001 Chicago Afternoons.

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