"The possibility of this kind of reaction to a police-involved shooting, that's what kept me up at night," said Sharon Fairley, former chief of the Civilian of Police Accountability (COPA).
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Fairley was chief of COPA when the agency transformed the way it investigates police-involved shootings.
"What we're seeing right now is the result of the lack of trust and the lack of legitimacy, the lack of perceived legitimacy in the community because of the decades-long frustration with policing," she said.
"It's a national disgrace. It's a global mockery," said Rev. Gregory Livingston, community organizer.
Livingston has organized several protests against police brutality and wants to see system reforms accomplished peacefully.
"You see that crowd gathering, get away," he advised those tempted to lash out. "Move away from it. You know what they're gonna do, get away from it. And those that decide to stay have to deal with the consequences of staying."
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"The youth is fed up and terrified," said David "Iggyflow" Rucker, community organizer.
Rucker, known as Iggyflow in the music world, said he understands the frustration and desperation so many in Chicago's Black community feel, especially during the pandemic. But, he said, he wants to see lasting changes between the police and the community.
"Looting is the wrong approach," he said. "But we need leaders out there to still allow people to protest, still to allow the message to be heard."
A Black Lives Matter Chicago car caravan and protest had been scheduled for Tuesday evening in support of Englewood residents after the police-involved shooting, but it was called off after neighborhood residents asked protesters to leave.
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The group was gathering outside the local police precinct when community members intervened. They said Englewood residents have been working to build a relationship with the police and they did not want protesters coming from outside the neighborhood.
"No matter what they were gonna do, they weren't gonna come to Englewood and antagonize our police," said Darryl Smith, president of the Englewood Political Task Force. "We have a relationship with the commander and if anyone wants to come in here and talk to the police about the shooting or anything, they have to go through us."
Protesters that had already gathered outside the Englewood precinct left after residents asked them to do so.