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Wild afternoon shootout leaves ‘gunpowder in the air’ on crowded street in the shadow of downtown high-rises

It was the evening rush hour Wednesday, and Milwaukee Avenue was crowded with people running errands, leaving work, walking their dogs.

Chicago police work the scene where multiple people were shot near the Grand Avenue, Halsted Street, and Milwaukee Avenue intersection, in the West Town neighborhood, Wednesday, Sept. 29, 2021.
Chicago police work the scene where multiple people were shot near the Grand Avenue, Halsted Street, and Milwaukee Avenue intersection, in the West Town neighborhood, Wednesday, Sept. 29, 2021.
Tyler LaRiviere/Sun-Times

In the shadow of half a dozen gleaming downtown high rises lies a stretch of Milwaukee Avenue that needs but shuns attention.

A square of plywood covers a window in the door at Richard’s Bar. Inside, a middle-aged man with a lighted cigarette in his hand asks to be left alone.

To get service at the messenger business two doors down requires a stroll down a reeking alley to a scuffed metal door with no sign on it.

The two blocks of Milwaukee between Grand and Hubbard may appear neglected, but for many it’s their way into and out of downtown. A short stroll away, at Grand and Halsted, new condo buildings and hipster bars crowd the intersection.

Wednesday evening, the street was jammed with people running errands, leaving work or walking their dogs when gunmen hanging out of car windows wildly fired at another car.

“There were people diving, and there was gunpowder in the air,” said Steven Caruso, the man behind the door at Advanced Messenger Service.

Crime scene tape wrapped on some fence near N Milwaukee and W Hubbard in the Fulton River District Thursday, Sept. 30, 2021.
Crime scene tape wrapped on some fence near Milwaukee and Hubbard, Thursday, Sept. 30, 2021.
Anthony Vazquez/Sun-Times

Five people were hit. One was riding a bicycle, another was in the backseat of a ride-share. One man was shot in the back and taken to the hospital in critical condition.

One West Town resident said he was driving with his wife down Milwaukee Avenue — just minutes from their home — when the gunfire started.

“There’s a park right there. It was such a beautiful day. I can’t tell you how many people were in the street,” he said. “The Starbucks patio was packed, there were literally 20 people crossing the street there at Jewel.”

He was near the Metra tracks when he heard a popping noise and turned to see a person with a gun hanging out the window of a car speeding toward him.

“I said to my wife, ‘Get down, get down,’” said the resident, who didn’t want to be named. “I needed my wife to survive to raise our daughter. That was the only thing that popped in my head.”

He heard the car pass then saw someone open fire on a car stopped in the intersection. “He was just firing into the car endlessly — 20, 30 bullets — I could see the metal flying off. The only place I’d ever seen that — in a movie.”

The two cars sped off. The resident saw a biker who had been shot and called 911. Another pedestrian ran over and took off his shirt to apply as a tourniquet.

“I realized we were in a war zone for that two and a half blocks and very lucky to be alive,” he said.

Chicago police work the scene where multiple people were shot near the Grand Avenue, Halsted Street, and Milwaukee Avenue intersection, in the West Town neighborhood, Wednesday, Sept. 29, 2021.
Chicago police work the scene where multiple people were shot near the Grand Avenue, Halsted Street and Milwaukee Avenue intersection, in the West Town neighborhood, Wednesday, Sept. 29, 2021.
Tyler LaRiviere/Sun-Times

The resident and other people who frequent this stretch of Milwaukee said they rarely hear gunfire, and the shooting was a shock.

People get a little rambunctious outside Emmit’s Bar on St. Patrick’s Day. And a few years ago, a man danced naked outside a nearby Italian restaurant.

But police data shows shootings have been spiking around there this year.

There have been at least nine people shot this year in the police beat that covers where the shooting happened. There was just one shooting victim there all of last year, a fatality; one shooting victim in 2019; none in 2018; one in 2017; and two in 2016.

There were two shootings reported in the beat last week: A woman shot while sitting in a car, and a man who showed up at his girlfriend’s home with gunshot wounds to the chest and back.

On Thursday, scraps of knotted police tape still fluttered on rusting lampposts along Milwaukee. On the sidewalk under Metra tracks, a discarded latex glove lay a few feet from what appeared to be a pool of dried blood.

At Richard’s, the handful of patrons in the bar either didn’t see the shootout or preferred not to discuss it.

Then one customer, playing a video game, turned and barked: “Call the mayor! Ask her what happened. She’s got all the answers.”