A Downtown Chicago Story

I was downtown after work, for an in-person happy hour with some coworkers along the Riverwalk. We’ve had several new folks join the team, and it was a nice chance folks to gather again.

Our downtown office is open again, and folks are starting to go back in. I’m still not yet comfortable with the idea, and will likely work remote as long as I’m able.

Hard to believe that it’s been over a year since I saw some of my coworkers in person.

The story I wanted to share though – happened before I met up with folks.

This was my first visit downtown again in… a year and a half. I snapped this photo right before walking across the street, and looked up to see this guy standing a few steps into the intersection, yelling “Hey!” loudly and repeatedly.

In crossing the street, I’m getting closer and closer to this guy. And I notice he’s got one of those sailor hats on. I’m not sure what the actual name is for this kind of hat – it’s white all over, with yellow decorations. And a kind of black brim?

At first, seeing it made me think of the guy from Gilligan’s Island. But in hindsight, it really matched the captain from The Love Boat. The hat looked like this.

So the thing of it is – this guy had on pretty normal looking clothes. And this really formal looking cap. Which seemed super out of place, given his outfit.

As he was standing in the street yelling, I slowly realized he was yelling at a cab that was waiting to make a turn. The yelling guy got angrier and angrier, I think because the cabbie was ignoring him (pretty sure the cab’s light was off).

Not two minutes into my return to downtown Chicago, and this is what I see. The thing of it for me though: as this guy got angrier and angrier, it was hard to take him seriously because of the hat.

If he was more formally dressed in naval attire, he would have seemed like an officer who was trying to catch a ride. But he was wearing lounge-y, tourist-y clothes, with this captain hat as a topper.

At the height of his anger, the guy started to yell things to himself and began walking back towards the sidewalk. I kept one eye on him, but also steered a pretty wide berth as I walked by.


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