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‘Pretend It’s a City’: A Response to a Non-Chicagoan Politely Wondering What’s Wrong With Chicago

09.12.2025 by David Murray // Leave a Comment

So apparently Trump has decided not to take on Chicago, and now has the Memphis mayor begging the Tennessee governor to say no to Trump, because “to have individuals with military fatigues, semi-automatic weapons and armored vehicles patrolling our streets is way too far, anti-democratic and anti-American. I think we’re on the brink of something that is going to change all our appreciation for freedoms. The way you can take away democratic liberties is to make sure people don’t have a way to protest, and the way to do that is to patrol the streets with military vehicles.”

Making temporarily moot, I guess, the post I had planned for today. Well, maybe the folks in Memphis can take courage from it. —DM

***

An acquaintance from Not Chicago got an earful last week when he innocently asked, “What’s going on in Chicago?”

“Nothing is going on in Chicago!” I shouted, telling him the weather’s been beautiful, the birds have been chirping, and all I see when I ride my motorcycle around all day is young people sitting in the grass in Humboldt Park at night and I’ve been sleeping outside on these cool nights, on my back porch—none of which was happening when I moved to this town in the early 1990s.

Well, I told him some of that, anyway.

I didn’t tell him that when my sister moved here a couple years later, my Ohioan dad bought her a pistol to carry around in her purse. When she objected that it was ridiculous, he protested, “But it’s nickel-plated!”

I did not tell him that said sister—and my then-girlfriend and best pal—got threatened on a midnight el train through the West Side in 1993 by some guys who were talking loudly about killing the lads and raping the women. The guys got off at the Homan stop, and we continued to Oak Park Avenue, shaken, sadder and wiser.

I did not tell him about the day 20 years ago that I decided to combine a run with a visit to site of the terrible 1958 Our Lady of the Angels school fire in what’s now an all-Black neighborhood. A nine-year-old boy rode up beside me as I ran and asked me what the fuck I was doing there. (It was a good question.)

I also did not tell him that I once broke down in my 1964 International Harvester Scout next to the worst housing project in Chicago and two guys ran into the building and got buckets of water and filled my radiator, not knowing I was going to give them a $20 in astonished gratitude. Driving away, I realized if the breakdown had happened in the Gold Coast, I’d-a been screwed.

Nor did I tell him about the hot summer night when my brother-in-law and I pulled up—also in the old Scout, which didn’t feature a roof—to a stoplight on a corner where the fire hydrant had been opened. And the two little boys on the opposite corner looked at us, and we looked at them, and all four of us knew what had to happen next. And we all belly-laughed as they channeled a geyser across the intersection, over my windshield and onto our heads.

To the Acquaintance from Not Chicago, I am sorry I overreacted and that I added, “All that’s going on in Chicago is Chicagoans trying to keep that motherfucker and his troops the fuck out of Chicago.” But I’m also sorry that I didn’t add:

No one sent the National Guard to Chicago when it burned to the ground in 1871 and Chicagoans had to rebuild it themselves. No one sent the National Guard to clean up Chicago’s Levee District in 1880, when women were being forced into sex slavery by the hundreds. No one sent the National Guard to quell the Haymarket Riot of 1886. No one sent the National Guard during the Pullman Strike the very next year, when 30 died in riots. No one sent the National Guard to protect people during the race riot of 1919, where 38 people died, mostly at the hands of roaming white gangs. The National Guard didn’t stop Al Capone (the IRS did). And when the National Guard did come in response to protests at the 1968 Democratic National Convention, their actions alongside the Chicago police were later broadly described by a new term, then: “police riot.”

The Onion cracked everybody up with the headline, “Chicago Air Now 75% Bullets.” (“According to our measurements, the proportion of bullets in Chicago’s overall air composition is significantly higher than that of other cities with comparable sizes and population densities. Frankly, if this trend continues—and there is unfortunately little evidence suggesting otherwise—living safely within the confines of Chicago will be almost impossible.”)

That was eleven years ago, in 2014!

And now they’re sending in the National Guard? Forgive us for questioning the timing, the wisdom and the likely long-term effectiveness.

Thank you, Not Chicago Acquaintance, for mumbling our mutual way out of that conversation by attributing the Chicago controversy to media exaggerating things “on both sides.” I don’t believe that, but it got us on to a happier subject.

In the great documentary Pretend It’s a City, the humorist Fran Lebowitz says, “When people say, ‘Why do you live in New York?’ you really can’t answer them, except you know that you have contempt for people who don’t have the guts to do it.”

I promise you, I do not feel that way.

Because that would be just as ignorant as feeling the other way around.

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