Have a president and a city ever hated each other as much as Donald J. Trump and Chicago?

The relationship between the two can best be described as:

A. A stalemate of mutual loathing.
B. An unbridgeable chasm of disgust.
C. A hatred deeper than that between the Bears and the Packers.
D. A rocky place in which mutual affection can find no purchase.

To try to understand why there’s so much enmity between our former president and our fair city, I wrote him a letter, and mailed it to Mar-a-Lago. I’m reprinting it here.

Donald J. Trump
Mar-a-Lago
Palm Beach, Florida 

Dear Mr. President,

You’ve been talking trash about our city for over a decade now, and I’m trying to figure out why. I mean, what have we ever done to you? We let you build a skyscraper along the river and affix your name to it in 10-foot-tall letters, so everyone who goes downtown knows it’s owned by TRUMP. Sure, we like to take pictures of ourselves giving it the finger, but that’s just a little fun we have on Instagram. It’s nothing personal against you. I’m sure you’ve made a lot of money off your condo and hotel here. One of our aldermen, Ed Burke, even won you a big tax break. Ed was recently convicted of several felonies and is going to federal prison, but we don’t hold it against you that you associated with a crooked Chicago politician. We know that’s how business is done in this town.

Our last mayor, Lori Lightfoot, said you used Chicago as a “punching bag.” Hey, we understand. That’s how you do politics. Ever since you rode down that escalator and blamed immigrants for crime and murder, you’ve been looking for enemies to rile up your supporters and bind them to your cause by raising the threat they pose to the American Way of Life. At Tuesday’s debate, it was immigrants eating dogs and cats in Springfield, Ohio. Many of your supporters live in owns so small that not even John Mellencamp would write a song about them. (Which is a bit odd, because you’re a New York real estate magnate and a Hollywood TV star.) You need to frighten them with scary stories about life in the big city, so they’re glad they don’t live here. You’re obviously not going to choose New York, because it’s your hometown, or L.A., because you love the celebrity lifestyle there, so you pick on Chicago. We’ve made ourselves an easy target, because we have more murders than either of those bigger cities. Still, some of your rhetoric is just…ungentlemanly. When you came here in 2019, for an international police chiefs convention, you called our city “embarrassing to us as a nation” and said that “Afghanistan is a safe place by comparison.” As a guest, that was rude. Fact check, Mr. President: more people die by violent means in a month in Afghanistan than die in a year in Chicago. We haven’t actually had a war here since 1812, when the Potawatomi massacred a bunch of settlers at the Battle of Fort Dearborn. But your running mate, JD Vance, didn’t mention that when he called Chicago “a war zone.” 

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Maybe you’re still sore because we shut down your rally at the UIC Pavilion in 2016. No other city ever shut down a Trump rally, but Chicago knows how to organize. This is the birthplace of community organizing, as you may have heard from your predecessor. One of the protestors brought a sign that said, “Trump Puts Ketchup on His Hot Dog.” Don’t take that personally, either. We say that to all out of towners. And when the Wiener’s Circle sold a three-inch hotdog called the “Trump Footlong,” that had nothing to do with your wiener. We know there’s “no problem there.” You told us during a debate.

Do you have it in for us because only 15 percent of the city’s voters cast their ballots for you? Don’t take that personally, either. We always vote for Democrats. Voting Democratic is a local tradition, like rooting for the Cubs or the White Sox. Chicago never voted for Ronald Reagan. Or Richard Nixon. We did vote for Abraham Lincoln, but that was a long time ago. The cops in Mount Greenwood and Edison Park voted for you, though. They like your stand on law and order. So did the Orthodox Jews in West Rogers Park. They like your support of Israel. So you can leave those neighborhoods out the next time you attack Chicago. We haven’t even elected a Republican mayor since 1927. I’m sure that’s another reason you run your mouth about us. You want to tell your supporters that “Democrat-run cities” are crime-ridden ratholes that can only be cured by Republican policies. That’s why you sent the FBI, the DEA and the U.S. Marshals here and took credit for a drop in the murder rate, even though it was already dropping before they got here.

Your list of put-downs goes on and on. We’re a “shooting disaster.” “Crime is out of control.” “Carnage.” We hope you don’t have a platform to insult us for four more years, but if you do, find another city to pick on. Like Cleveland. Their murder rate is much higher than ours. And they’re used to being the butt of jokes.