Hi — Mark Jacob here, contributor at COURIER.
Donald Trump is threatening to send the U.S. military into Chicago — treating one of America’s greatest cities as if it were enemy territory. As someone who’s spent decades reporting here, I know Chicago isn’t the “hellhole” Trump smears it to be. It’s a city of resilience, defiance, and progress — qualities Trump can’t control and will never understand.
I wrote about what Trump gets wrong about Chicago, and why his attacks are really about silencing dissent and dividing Americans. You can read my full piece below, but before you do, I hope you’ll consider supporting COURIER.
Thanks for being in this fight,
Mark Jacob
Chicago doesn’t care what Donald Trump thinks.
It doesn't need him and doesn't want him. It wishes he would go away.
That no doubt infuriates Trump and is one reason he’s threatening to impose a military occupation on the city as if it were a foreign capital captured in war.
Trump likes to lie about Chicago, to exaggerate its faults and ignore its virtues. And that spin finds an eager audience in people who don’t get out much and don't realize that even the best cities are beautiful messes, with great strengths and great flaws.
While Trump is a fairly recent virus infecting America, Chicago has long contributed to the cultural and economic health of the nation.
It’s the birthplace of the zipper, the Ferris wheel, softball, house music, the skyscraper, the controlled nuclear chain reaction, and “The Wonderful Wizard of Oz.” On the negative side, it was home to the nation’s most notorious political convention, its most famous gangster, and its deadliest theater fire. Not to mention the love-it-or-hate-it bitter liqueur, Malört.
Chicago is a lot of things, but it’s certainly not a “hellhole,” as claimed by the convicted felon, sexual predator, and pathological liar in the White House.
I’m the former metro editor of the Chicago Tribune and have lived in the Chicago area for four decades. I’ve seen plenty of good and bad, and I know the good wins out.
One of the most admirable qualities of Chicagoans is their defiant attitude, something Trump doesn't understand because he surrounds himself with toadies. The undaunted figures in Chicago history include:
- Ida B. Wells, the courageous anti-lynching crusader
- Studs Terkel, the leftist writer and broadcaster who was disappointed to learn his wife’s FBI file was bigger than his
- Saul Alinsky, the community organizer who inspired Barack Obama
- Jane Addams, the social worker whose pacifism during World War I went against the political tide
- Fred Hampton, the Black Panther leader whose assassination by the police and FBI is still not forgotten in Chicago today
- Henry Gerber, founder of the nation’s first gay rights organization
Chicago’s refusal to submit to authority was personified by a character named George Wellington Streeter. The eccentric captain’s boat ran aground along Chicago’s lakefront in 1886 and he stayed there, inviting local builders to dump their debris around his boat and turn it into landfill. He declared the resulting land to be the District of Lake Michigan, unaccountable to Chicago or Illinois officials. It took decades of court fights to reject his claim, but the captain had the last laugh: the ritzy downtown neighborhood now on the site is known as Streeterville.
As Trump tries to strong-arm Chicago, he should remember the city has always attracted people who challenge the power structure.
There were the “Haymarket martyrs,” four anarchists hanged unjustly after an 1886 police clash with protesters led to deaths on both sides. A fifth anarchist avoided the hangman when a blasting cap was smuggled into his cell and he set it off in his mouth, dying hours later. Chicagoans do not go down quietly. (The anarchists’ demand was radical indeed: an eight-hour workday.)
Chicago’s resistance is not just ancient history. On Labor Day 2025, block after block of protesters paraded through the city, laying out the unwelcome mat for Trump. They started their march at the Haymarket Memorial.
Another old confrontation remains relevant today. During the often violent Pullman strike of 1894 between rail workers and big business, President Grover Cleveland sent the military into Chicago over the objection of Illinois’ governor – just as Trump is threatening to send the military here now over the objections of current Gov. J.B. Pritzker and Mayor Brandon Johnson.
Chicago will sue. The people will protest. The spirit of defiance remains alive and well today.
And Chicago has another fine quality: resilience. It survived Haymarket, the Pullman strike, and the Great Fire of 1871. It survives Malört on a daily basis. It can survive whatever Trump does to us.
Author Finis Farr called Chicago “the most American city,” but I think he was wrong. No single place in this country is more American than another. One of the worst poisons that Trump has dumped into our national mindset is the idea that Americans should hate or dismiss other Americans – that it’s red vs. blue, North vs. South, Christians vs. Muslims, white vs. Black and Latino.
Chicago’s doors are open for everyone. Except, that is, an army of occupation sent in by Donald Trump.
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In solidarity,
The COURIER Team