Saturday’s “Day of Protest” in Chicago seemed to hit differently than others before it. Though the police killings of George Floyd in Minneapolis and Breonna Taylor in Louisville sparked the flame that ignited thousands to protest and march against the murder of unarmed Black folks across the country, in Chicago, a deep wound is reopened. 

We’ve been here too many times. The deaths of Rekia Boyd, Laquan McDonald and many more leave Black Chicago with an unhealed heart. The decades of police brutality and torture, the latter most notoriously spearheaded by former Chicago Police Commander Jon Burge and his notorious Midnight Crew, left a bad taste in the mouths of Black Chicagoans with a strong distrust in the police. These things, combined with the heft of a pandemic that is still disproportionately handicapping Black people, makes these protests feel particularly dire.

It was after 10:00 p.m. on Saturday, when I finally returned home after about eight hours of navigating crowds of protestors, marching and running for miles and capturing footage of various demonstrations. My only thought was, where do I begin to attempt to recap the movement and the motivations of protestors making their voices, pains and struggles heard in downtown Chicago? It seemed impossible, not just because of the sheer scale of the event, but because everyone’s movements and motivations seemed to splinter so frequently that the crowd of thousands became gatherings of hundreds and slowly groups of tens. 

But I had to. Having been covering the protests live from the ground and fielding the response of thousands on social media, it became clear to me in their reactions, that this day warranted more than a Twitter takeover.

Saturday's "Day of Protest" started around noon with car caravans and marches into downtown Chicago from various locations across the city | Photo by Darius Griffin/The TRiiBE
The car caravans and marches met up near the Daley Plaza in downtown Chicago before spilling into the rest of the downtown area | Photo by Darius Griffin/The TRiiBE

Around 2:00 p.m on Saturday., I began my march at the Metropolitan Correctional Center where hundreds — led by organizers from Chicago Alliance Against Racist and Political Repression (CAARPR), Black Lives Matter, and more — gathered to protest in solidarity with inmates who, just the night before, participated with those protesting Floyd’s murder by flickering their lights and making noise. Now, they banged on walls to make their support known. Then I made the journey to Daley Plaza, where we all were joined by thousands more independent protesters. 

At the Daley Center, a cacophony of car horns, instruments and varying chants surrounded the leaders of BYP 100, Black Lives Matter Chicago and other activist organizations who gave speeches to remind people of the mission: to protest the unlawful murders of Black people at the hands of police. Meanwhile, other protestors paraded around the building on bikes, cars, skateboards, electric scooters and their feet. The noise made it clear that the goal was to be heard; a goal that seemed to be shared by all demonstrators. 

The Chicago Police Department (CPD) presence was minimal at first with just a few cars blocking off intersections. At about 3:30 p.m., they began to pour in as protesters began to venture out of the Plaza, and the flames of confrontation were stoked when officers disrupted marching routes.

“They’re not out here to protect us. They never did that,” says Mike, a protester who agreed to be interviewed but refused to have his full name used. “They just want to make us easier to deal with.” 

Mike was one who remained on the front lines for hours. Throughout the early stages of the protests, he helped a team of protesters cut down an American flag from the side of 28 N. Clark. His request for anonymity, he explains, is a survival tactic. 

“I’m not trying to be the next to go M.I.A. all of a sudden,” he says. He references the occurrences of six Ferguson, Mo., protesters who died after images of their insurgency circulated through the media.

Chicago Police officer making a face at a protestor | Photo by Darius Griffin/The TRiiBE
Chicago Police blocking protestors from crossing a bridge at Wacker Drive | Photo by Darius Griffin/The TRiiBE

It would seem based on the movement of officers — cutting off protesters in the middle of marches, and dispersing small squadrons into the crowd to redirect their attention — that Mike was right. It seemed that the goal of the police was to turn the army of protesters into smaller, more manageable factions. 

For example, as protesters crossed the Wabash bridge near Wacker Drive toward Trump Tower, police formed a hard-line on the end of the bridge, separating demonstrators at the entrance of the building from an even larger group that never got the opportunity to cross. 

“They’re out here in all this gear and blocking off people marching and [the protesters] haven’t even done anything yet,” Cujo Dobbs, one of many protesting from their cars, said about the police presence. “Like they want people to act up.” 

Dobbs was on his second day of protest, having participated in demonstrations the night of May 29, where more than 100 people were arrested downtown. Dobbs called the scene at Saturday’s “Day of Protest” tame in comparison, mainly because protesters were not being arrested en masse up to that point.

“I’m sure when the sun goes down it’ll be the same story,” Dobbs adds. He opted to remain in his car and use it to provide shelter if anyone needs it. “All this is leading to Michigan Avenue,” he concludes. Some folks protesting from cars are blasting music, some are holding signs, many with quotes of support like “No Justice, No Peace,” painted on. They drive along protesters throughout the marching route.

Both protesters and CPD officers saw the Magnificent Mile as the prize. Police, it seemed, because letting the uprising spill onto one of Chicago’s busiest corridors would prove to be devastating. Protesters, mostly because what better place to get national eyes on the movement than the city’s commercial centerpiece. Cops did everything in their power to halt the movement to Michigan; lifting bridges, and setting up barricades of personnel on access streets, forcing protesters to occupy Lake Shore Drive en route to the shopping mecca. 

“They don’t want us to f*ck those stores up,” says one protester who declined to be named for her own safety. 

“They were cool with us staying over here spray painting A-C-A-B on concrete,” she says. “This honestly proves everything we’re out here for. [Police] care about property more than people. And when we get there, that’s when they’ll pull out the big guns.”

A vehicle set ablaze | Photo by Darius Griffin/The TRiiBE
A CTA bus with a coat of spray paint | Photo by Darius Griffin/The TRiiBE

Police tactics were definitely working to some degree to split up protesters, but there was an even greater division that began to take shape. One that the protesters created themselves, one that didn’t rest along racial, gender, or other barriers. Instead, the greater division was in the methods of protest. By 5:00 p.m., the migration toward Michigan Avenue continued.

Some remained at Wabash and Wacker, confronting cops head on, even nearly toppling a police wagon at the intersection. Here, the air smelled of a mix of spray paint and various bottled liquids that have been busted against police vehicles. It seemed with this group, the focus of the demonstrations were most clearly on the fight against police brutality.

Meanwhile, some protesters who successfully infiltrated the Magnificent Mile began looting stores. The signature sound of the protest had shifted from “Say His Name” chants to store security sirens. Cops were stationed at the, now raised, Michigan street bridge and made no effort at preventing the ransacking of the Magnificent Mile establishments. (Only once the curfew went into effect did I notice police pulling looters out of stores).

Another group entirely, having no interest in looting, began setting cop cars ablaze and throwing firecrackers toward crowds of cops. The unexpected booming of M80 fireworks drew the attention of SWAT carrying weapons that resembled tear gas guns. One cop tells me she can’t say what the weapons are. Another calls them “firework diffusers.”

Some demonstrators continued to float between locations, spectating almost, or simply adding their voices and bodies to the larger gatherings they found nearest by.

A Chicago Police squad car on fire | Photo by Darius Griffin/The TRiiBE
A camera shop covered in graffiti | Photo by Darius Griffin/The TRiiBE

As night fell, around 8:30, the police presence became more aggressive. As news of the mayor’s new 9 p.m. curfew spread, the crowds began to shrink. Now, the separated factions became small groups of less than 10, scattered across downtown Chicago. Some were making their way home as the curfew enforcement began, others remained holding the line against law enforcement as the Illinois State Police joined CPD, others still, looting what inventory remained of Macy’s on State Street.

As I made my way out of downtown, past burning trash cans and a 7-Eleven store with smoke billowing out of its demolished windows, police officers suited up like military personnel, and motorcyclists burning rubber in solidarity with protesters, I faced three separate encounters. First, a young black man who I allowed to use my phone to find his iPhone. Next, a group of riot-armed cops who forced me to drop the plastic CVS bag I was carrying — which contained two bottles of water, a half-used gallon of milk I brought from home and my own CamelBak bottle — at the threat of being arrested for looting.  After my attempts at explaining my CVS bag fell on deaf ears, I complied, and kept it moving. I was at risk of being added to the total of about 240 who were arrested that night, according to CPD Superintendent David Brown.

Finally, I ran into a familiar face, an old high school teacher known simply as “Abrams.” I explained that I was here covering the protests for work. “It’s good to see you out there doing this,” he says. “We’re trying to hold the line out here. So it’s good to see you doing what you can.” 

Abrams explains that it isn’t his first time out like this and it likely won’t be his last. “You be safe out there.”

is a staff writer with The TRiiBE. Email him with news tips.
is the editor-in-chief of The TRiiBE.