Miguel Salgado, the owner of Angel's Tire Shop on 18th Street, said a customer had just pulled up for what should have been a quick fix Sunday morning when the incident happened.
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Seconds after the driver got out to greet employees, a blue sedan pulls up and out of view from surveillance cameras. Before you can even see a gun, the customer and employees' hands shoot into the air in apparent immediate surrender.
"They came out of the car and told us not to move, hands up, where's the money," Salgado said.
Two masked men with guns rifled through the pockets of the customer and two tire shop employees, one just out of frame of the camera.
"It's not every day you wake up to a gun pointed at you," Salgado said.
One of the men kept waving a handgun, while the other was armed with what appeared to be a long gun. They took hundreds of dollars in cash and the customer's keys before speeding off in the Jeep.
READ MORE: CPD agrees to increase patrols in effort to help protect street vendors, community leaders say
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Around the same time, Salgado said at least two masked men held up a tamale vendor a few blocks away near 21st and Damen.
Chicago police confirmed that several victims and street vendors were robbed.
"This is really tragic. We talk about street vendors who work eight to 10 hours a day in the freezing cold with the little that they gain and now they're being robbed," said 25th Ward Alderman Byron Sigcho-Lopez.
Southwest Side community leaders said vendors, who work to cobble together a humble living with just cash, are being targeted and terrorized.
"The worst part of all, I'll be completely transparent, is that when the street vendors have complained to the city about the issue of public safety, they have not deployed more safety, they have deployed more inspectors. And that is a tragedy," Sigcho-Lopez said.
Police said no one is in custody for these armed robberies.