#697: The Woman in the Dick Tracy Hat

October 10th, 2016

Here’s the story, all its parts:

I was sitting in a leafy spot by the federal prison parking garage, waiting for a tour group for the walking tours I run.

Across the street, a lady walked by with a Dick Tracy-style yellow fedora. She had a milk crate slung in front of her. When she passed a beggar, she pulled a plastic-wrapped sandwich out of the crate. He looked at her, she looked at him, and he took the sandwich.

She kept walking south and I lost her behind an SUV at the stoplight.

That’s it. That’s all. And wow.


I say wow because I don’t know what was going on, why the woman had a Dick Tracy hat and a milk crate full of plastic-wrapped meals.

It could have been a Chicago Marathon thing. The run had just ended an hour or so before, so maybe she was unloading some unwanted racer fare on a hobo.

Or maybe it was a charity thing, like she was playing comics page grandstander for an afternoon, trading sammiches for moral superiority around South Loop.

Or maybe she was just a lady with odd fashion sense who happened to have a sandwich and a beggar at the same time and did the math as I watched from a leafy spot by a prison parking deck.

No matter the reason, here’s the why behind the wow: No one was watching.

Sure, I was, but she didn’t see me. There were no furtive glances across the street or even recognition that I was a thing that was.

There were a few late marathoners hobbling by wrapped in those post-race tin foil blankets, the yearly Limping of the Skinny that plagues this sacred day. But they weren’t watching anything other than their limps and growing corns.

No, this appeared from all indices to be a real and rare genuine example of unwatched generosity. The kind act captured in the wild, a real-life human offering a real-life human a bit of human kindness without any thought of social reward.

Whatever her reasons, the woman in the Dick Tracy fedora did a good thing, not even realizing anyone was there to chart her good deed. She did something nice, then moved on.


That’s my Chicago story for the day. That should be my story for the month, week, year, but I don’t know if it will happen again.

I don’t know how many people are kind when no one’s watching.

Talk politics with me at “How to Steal an Election,” a booze-fueled tutorial I’m running with Atlas Obscura and the Room 13 speakeasy a week before the election. Swill craft cocktails while I take you through decades of COMPLETELY LEGAL voter manipulation in Chicago and elsewhere. Fun, civics and the best damn Old Fashioned I’ve had in years. Tickets are going fast.

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