The scene unfolded near the Belmont Red Line stop. Belmont Avenue was shut down for hours as hundreds blocked the street.
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"I came out of my show, and I looked down the street, and there was just a mob," said Dominic Rescigno, whose car was damaged.
Rescigno was performing improv at a nearby theatre, when he saw the large crowds begin to gather around 9:30 p.m., preventing him from reaching his car.
"A bunch of cops standing around watching it, and I went up to one of them and said, 'my car is there,' and they said, 'well you're not getting it tonight,'" Rescigno said. "I looked down, and there was just a mob of people and a bunch of cops standing around, watching, and I went to one of them and said, 'My car was in there,' and he said, 'You're not getting it tonight.'"
On Tuesday morning, he and Cody Ellsworth were horrified by the extent of the damage.
People had rummaged through their car, opening their glove compartment, stealing items inside, they said, and ripping out their catnip from the trunk, spilling it on the street.
"He started crying; we just got it in December, and we pay a hefty car payment, and we love it. It takes care of us in many ways, and it's sad to see it," Ellsworth said.
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One resident was just trying to go out to get something to eat.
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"It was kind of like I was in a club. Everyone was dancing, twerking, drinking. That was kind of the scene," said Nirai Mohankumar.
Yolanda Ace also weighed in.
"Everybody was having a good time, but the party was Sunday, not Monday. But, the party kept going. They continued until who knows how long," Ace said.
44th Ward Ald. Bennett Lawson was out surveying the damage Tuesday morning.
"I live a couple blocks away, so I heard the police helicopter at about 9:30," Lawson said.
Streets and sanitation crews were cleaning the roadways.
He said officers were there trying to break up the crowd, as more and more young people were arriving, with each train on the CTA.
"I have to talk to the CTA. They need to be a partner in our success, and in our safety, and they are. But, understanding people need to move through the city, but when it's appropriate to close the Belmont station, we should be able to do that," Lawson said. "I think every year, we make tweaks in the plan for Pride, and everything that happens around it. We have to start to figure this thing better."
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Lawson said a similar incident happened on this day last year after the Pride Parade.
As it gets further into summer, he said, "I want to talk with obviously the 19th District and the folks at CPD, work with the mayor's office and my colleagues so we have a strategy for these young people."
Larson's chief of staff said there have already been conversations on Tuesday with the agencies involved about Monday night, and more are planned to keep everyone safe.
Chicago police said two people were arrested in Monday night's incident, including a 15-year-old girl. She was charged with aggravated assault of a first responder, resisting and obstructing traffic.
CPD also issued a statement, saying, "The Chicago Police Department works closely with our City partners, including the Chicago Transit Authority (CTA) and the Department of Streets and Sanitation. We frequently collaborate and coordinate in public safety efforts and greatly appreciate their continued partnership and support in these efforts."
The CTA issued a statement as well, saying, "The CTA has a very close working relationship with the Chicago Police Department and other city agencies, and coordinates very closely with those entities on every event and activity, including adjusting service as necessary. CPD and CTA have protocols in place to address possible station closures, which are designed to ensure a balance between public safety and providing service to CTA customers."
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