What The Hell Happened to Chicago : THERE IT IS
By Michael Ledwith
April 17th, 2026
I met with two guys from Paris last week.
They suggested in the Loop across the street from the James R. Thompson Center.
I hadn’t been in the Loop for a couple of years but followed @CWBChicago on X for the latest on shootings, street takeovers, and general mayhem.
I emailed back that no one meets in the Loop anymore by choice. Let’s meet at the Firehouse Grill in Evanston.
Due to previous commitments they couldn’t switch.
Not wanting to screw around with parking I took an Uber.
Twenty minutes early, with time to kill, oops, an unfortunate choice of words in 2026 Chicago, I wandered around.
Empty streets. The massive, uglier behind construction screens, former State of Illinois building, looking squat and bunkerish. The godawful Howard Johnson blue and orange paneling gone.
I thought of the hundreds of state workers streaming in and out. Crowds of lawyers and lobbyists. Black Cadillacs idling on the LaSalle Street side. Various Governors surrounding by State Patrolmen scurrying in if facing indictment, or glad-handing glad handers and tousseling the hair of kids for the cameras, if not.
No cars idling on any side of the building. No cars double parked. No cabs circling the block in the age of Uber.
It was a cold, dreary, cruel Midwest April day.
Spitting rain. Windy enough to make using an umbrella a workout. Little traffic. No bikes in the bike lanes.
No young executives on the make in suits. No women VPs in high heels and business suits strutting to the next important meeting.
I was in a suit and tie, and felt like a Martian.
People stared.
Panhandlers straightened up at the sight of a suit, discarded their polished pitches about needing to take the EL to the shelter, and handed out a prospectus for helping them fund a new AI start-up…minimum investment five bucks.
The meeting lasted an hour. We talked about Paris. One of them surfed.
Walked out with a commitment to meet at the Firehouse Grill in Evanston next time.
They love pizza.
Turned left out the door heading north so I could walk along the river.
The rain was barely spitting and I thought: perhaps a stately saraband up the Magnificent Mile?
A late lunch at Gibson’s?
Would the movers and shakers and politicians and rich guys and young women seeking sugar daddies still be there?
I crossed the bridge to start the Mile.
First impression: Unter den Linden. Circa 1955. Grey and abandoned.
As with the once buzzing and crowded LaSalle and Madison, there were no crowds in the early afternoon of a weekday on Michigan Avenue.
No office workers. No one professionally dressed.
Knots of families huddled close. Mothers’ eyes darting this way and that, alert for danger.
Fathers puffing their chests and trying to like they could handle themselves.
Little girls clutching Molly dolls. Young families on vacation in the intermittent drizzle.
Nice but not magnificent.
The foreshortening of the avenue looking north from the bridge toward Oak making it seem semi alive and semi crowded.
But, it was a mirage.
No elbows needed to make one’s way up the Magnificent Mile.
Just a dispiriting solo trudge.
Not a celebration of what? The City of Big Shoulders? Mayor Daley? Making no small plans?
It was, at best, just another street. In just another big city. A big American city destroyed by politicians for reasons no one can fathom.
The Wrigley Building empty looking. It may have been the drizzle, but no gleam off the white façade.
The Tribune Building abandoned, a single light on in an office, as it is ‘repurposed’.
The beautiful Gothic windows facing the avenue looking as if there had been a fire.
Smoke stained.
As if the Adlon Hotel after the war.
Not the headquarters of the World’s Greatest Newspaper on a Magnificent Mile in one of the world’s greatest cities.
The triumphant artifacts brought back by Colonel McCormick and the Trib’s foreign correspondents to decorate its façade and proclaim THE CHICAGO TRIBUNE proudly, still there.
Brought back from the Parthenon. The Great Pyramid. The Hagia Sophia. Ankor Wat. Fort Sumter.
Omaha Beach.
To a confident Chicago. An American city on the go.
I wondered if wilding mobs had ever tried to pry them out? Or vandals ranging unmolested up and down the avenue attempted to destroy them? You know, just for the heck of it?
The office towers along the avenue seemed empty. Miranda Devine of The New York Post, noted that the commercial office vacancy rate was killing the city. And she posted a tweet from Nightingale Associates about this critical problem strangling the city of Chicago.
The restaurants catering to the crowds of office workers getting lunch or having drinks after work only exist in the mind of someone like me.
That was the cafe where I saw Eric Clapton, by himself, having a sandwich.
I had lunch over there with Frank Casey and Nick Nolte and a hundred pretty girls crowded around us. Chicago’s finest had to get us out. Then it was an Indian place. Now it is gone.
Audrey Hepburn, staying at The Drake where the Queen always stayed when in Chicago, having a milkshake at the Drake Drugstore.
Almost all ground floor display windows are covered with opaque material so mobs won’t be tempted to smash and grab.
Window shopping, gone with the wind.
Looting has been part of the Magnificent Mile experience for years.
Young, tough looking cops, standing in pairs every couple of blocks. Alert. Ready.
I stopped to talk to them. Nice guys. Very guarded in how they answered my questions about what it was like.
Things are better. People are mostly nice. No, you don’t come here after dark. No, don’t go off the avenue. No, don’t wander around Streeterville.
I caught a Vietnam era vibe as if I was talking to soldiers back from a tour or two.
The commonality for explanation of what it was like:
There it is.
Water Tower Place reminding me of the statue of Ozymandias.
Me, the traveler:
‘I met a traveller from an antique land,
Who said—“Two vast and trunkless legs of stone
Stand in the desert. . . .
…Nothing beside remains. Round the decay
Of that colossal Wreck, boundless and bare
The lone and level sands stretch far away.’
Or, streets, avenues, blocks, a city.
RL’s was pumping. A line for a table. The only semi magnificence on the avenue.
Oak Street.
Forever, the cherry atop of the Magnificent Mile.
It looks pretty much the same.
Still has products in the Oak facing windows.
But, standing outside, or just inside the door, tough looking security.
Two or three guards clustered at each entrance. More Spetsnaz than Andy Frain.
Gibson’s. Empty seats at the bar. A couple of tables with customers. Old ladies. No fortune hunters
The restaurant with empty power booths.
I flopped into one, wet and exhausted.
Wearing dress shoes to walk two miles after months of Danner Hiking Boots every
day, had a particular penance.
For old time’s sake, and in honor of the great Harvey Pearlman, I ordered a loud
mouth soup to drink.
The waitress, the floor manager, the maître ‘d, the general manager had no idea of what I was referring to.
No worries.
I got a beer and a cheeseburger.
I should have gone to the Billy Goat, skipped the depressing mile, and Ubered home.
The cheeseburger came with the cheese on the bottom of the meat.
Like the Magnificent Mile after the neglect and depredations of at least two Mayors, several Governors, and those of us who just stopped coming to Chicago as the better part of valor.
No more dancing beneath the diamond sky with one hand waving free on Michigan Avenue. In downtown Chicago. It’s gone.
Cheeseburgers in smart restaurants put the cheese at the bottom of the patty.
There it is.
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Frequent contributor Michael Ledwith is a former bag boy at Winn-Dixie, who worked on the Apollo Program one summer in college. A former U.S. Army officer, he ran with the bulls in Pamplona and saw Baryshnikov dance ‘Giselle’ at the Auditorium Theater. Surfer. Rock and roll radio in Chicago. Shareholder, Christopher’s American Grill, London. Father. Movie lover—favorite dialogue: “I say he never loved the emperor.”