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South Shore resident Dewayne Jackson couldn’t believe what he saw. As he left his friend’s apartment complex at 7500 S. South Shore Dr. around one or two in the morning on Sept. 30, Jackson saw militarized federal agents moving in on the building.
Masked agents in military fatigues rappelled from Black Hawk military helicopters and jumped out of cargo vans. They flashed lights onto the building that were so bright, Jackson said, it looked like “it was daytime.” Jackson said the scene looked like something he’s only seen in movies and TV shows like “The A-Team.”
“That’s how they came, like [Osama] bin Laden was in there hiding or something,” Jackson said.
Excel Academy sits next door to the apartment complex, separated by a gate. Jackson said agents cut open the gate between the school and the apartment building to “haul” people over.
Homeland Security filmed the raid and turned it into a high-definition sizzle-reel comparable to a trailer for an action movie. The total number of people detained remains unknown; agents with Border Patrol, the FBI and the Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF) reportedly arrested 37 people during the raid. They claim some of the targeted people are Latin gang members; they also say those targeted are accused of drug trafficking and distribution, weapons crimes and immigration violations.
Border Patrol told NewsNation when feds clear buildings during operations, “we’re going to clear the entire building, bring everyone out of that building, whether they’re United States citizen or an illegal alien.”
“They were kicking in doors, flash bombing people, telling everybody to get on the ground, even the Black people,” Jackson recalled. “A lot of people got locked up who had warrants… They had nothing to do with no Venezuelans.”
Rod Johnson will never forget federal agents zip-tying his hands behind his back. The 67-year-old military veteran already suffers from post-traumatic stress disorder. The night of the raid, Johnson said he was detained for two hours outside his apartment at 7500 S. South Shore Dr., where he’s lived for several years.
“I’m an American citizen with no warrants,” Johnson said. He never thought the presence of federal agents in Chicago would impact him. When asked why, he said, “Because I’m a Black man.”
Both sentiments from Jackson and Johnson aren’t too different from those expressed by a Black bystander in the viral video of the feds placing a Black man in a chokehold in Chicago’s East Garfield Park neighborhood: “Y’all supposed to be out here choking Mexicans,” he said.
Jackson described the happiness he felt when he first heard U.S. Immigration and Customs Enforcement (ICE) was coming to Chicago. He said he felt that the migrants were “slowly taking over” South Shore and said the building eventually had majority immigrant occupants.
After the South Shore raid, Jackson said his feelings have changed because ICE “had mercy for nobody.”
“They’re trying to start some type of war, Jackson said. “It wasn’t right, though. People still live in that building. They still got they door kicked in.”
A federal judge in Chicago stated that the South Shore raid violated regulations when it detained American citizens far longer than the “brief” period that is authorized, the Chicago Sun-Times reported. “ICE rousted American citizens from their apartments during the middle of the night and detained them — in zip ties no less — for far longer than the ‘brief’ period authorized by the operative regulation,” the judge wrote.
Last week marked a pivotal moment in the surge of federal agents occupying Chicago as part of President Donald Trump’s “Operation Midway Blitz” to deport “criminal illegal” immigrants. The South Shore raid, along with the raid at a Bronzeville homeless shelter and the chokehold in East Garfield Park, directly touched Black Chicago communities.
“They think that this is not our fight, it’s not our struggle, but they’re wrong. It is our fight; it is our struggle,” said Kenneth Phelps, pastor of Concord Missionary Baptist Church in Woodlawn. “I think this is just all a part of the President Trump playbook to agitate and aggravate Black and brown communities.”
Phelps’ church hosts bilingual service to accommodate the influx of Venezuelans and other Latin American migrants who were largely bused to the city by Texas Gov. Greg Abbott. While Chicago was seeing an influx of migrant activity, Phelps also worked with the Woodlawn-based initiative, Chicago4All, to help connect migrants to vital services.
Phelps said he believes that the incidents seen in South Shore, Bronzeville and East Garfield Park show that the goal of the tactics employed by federal agents is to provoke violence. That allows Trump to justify sending in the National Guard.
Despite local and state leaders suing Trump for sending militarized troops against their wishes, Texas National Guard troops arrived Tuesday to the Joliet Local Training Area in the suburb of Elwood.
“It’s not only just a brown struggle, it’s a Black struggle,” Phelps said. “And if we think that it’s not going to impact us, where do you think they’re going to send the National Guard? They’re going to send it to the African American community.”
RE-OPENING OLD WOUNDS
Trump’s immigration operation, coupled with the presence of federal agents in Chicago, is reopening wounds felt after migrants were bussed to the city in droves. Some Black people felt that migrants were getting services, such as housing and food assistance, ahead of a population that has historically and systematically struggled in this city.
In total, Chicago spent $640 million on the migrant crisis between 2022 and 2025, according to publicly available city data, with roughly $270 million coming from the city’s corporate budget and the rest from federal, state and county grants.
In April, The TRiiBE reported that the majority-Black neighborhood of South Shore was the top area where migrants were placed with the help of state-run programs due to the amount of affordable options and housing stock in the community.
South Shore has had the highest eviction rates in the city of Chicago and already suffers from decades of disinvestment. Such realities have led Black residents to be resentful of migrants, but neighborhood activists say such finger-pointing should go toward bad policies and opportunistic landlords that have taken advantage of migrants and longtime Black community members.
The South Shore building at the center of last week’s raid was already in bad condition. The TRiiBE reviewed inspection records filed with Chicago’s Building Permit and Inspection Records. The property at 7500 S. South Shore Dr. has had various building code violations. The building has not passed a Conservation Complaint Inspection since 2020, records show. It also has not passed an annual elevator inspection since 2022, according to those records.
Johnson, the 67-year-old military vet who lives in the building, said he saw what looked like federal agents at the apartment complex nearly two weeks ahead of the raid.
“They had been in the building like 10 days prior to that [raid],” Johnson said. “The doors was marked. They did a mass eviction and every apartment that was on the mass eviction, those basically were the apartments the immigrants were [staying in].”
Johnson’s account coincides with reporting by South Side Weekly, in which a source said they saw what looked like federal agents in cars and trucks parked near the school.
Real estate publication The Real Deal also reported that city inspectors visited the property two weeks ahead of the raid. According to The Real Deal, Trinity Flood — the owner of the building — is facing a $27 million foreclosure lawsuit.
Adam Skarie, who is listed as the registered agent of 7500 Shore LLC, was not available for comment. Skarie is also listed as the taxpayer of the property.
In a statement emailed to The TRiiBE about the property shortly after this story was published, the Department of Buildings (DOB) said:
“On January 16, 2025, the Department of Buildings conducted an inspection, citing various dangerous and hazardous violations that warranted an escalation of our enforcement process to the Department of Law, which is engaged in an active case in Circuit Court. As part of the court proceedings, the court ordered an inspection with the property owner to ensure our team had the necessary access to complete a comprehensive inspection of the property, which includes inspecting inside tenants’ units.”
According to the DOB, the inspection scheduled for June 23 was not completed due to police activity in the area. There were inspections scheduled for later dates on Aug. 6 and Sept. 19; those court-ordered inspections did not take place, according to DOB, because the owner was not present and did not provide access to the property.
“To date, this owner remains noncompliant with the Chicago Construction Code,” read the statement from the DOB.
A statement from the Mayor’s Office emailed shortly after this story was published stated, “conditions in the building were deplorable, which is why DOB cited it for violations on multiple occasions in an effort to ensure accountability for the residents.” The Mayor’s Office added that the raid by federal agents had nothing to do with the building’s conditions.
The raid highlighted subpar living conditions that have long plagued the South Shore community and what organizers in South Shore have been recently working to address by holding property owners accountable for abandoning residents. Activists continue to fight for housing protections as private investors have sought out properties in the area due to the forthcoming Obama Presidential Center.
This City Council recently passed the Jackson Park Housing Pilot to further provide housing protections to those in the area. The 7th Ward, where the 7500 S. South Shore Dr. property is located, is not included in the pilot. The 7th Ward is overseen by Ald. Greg Mitchell who has notably been opposed to the community benefits agreements surrounding the Obama Presidential Library that organizers have been pushing for.
"WE WERE ALWAYS GOING TO EXPERIENCE THE ATTACKS"
Chris Harris is the founder of social service agency Bright Star Community Development Corporation, which oversees the homeless shelter that was the site of federal agent activity in Bronzeville on Oct.1. Harris joined Mayor Brandon Johnson and other local officials during a press conference about ICE accountability on Oct. 6 to speak about his encounter with federal agents.
“Just a few days ago in our Bright Star homeless shelter in Bronzeville, the Black metropolis, ICE agents raided our facility without warning,” Harris said. “They came in, they handcuffed, detained, and took four residents. Let me be clear, they were not criminals. They were human beings, trying to survive…Our shelter is not harboring criminals.”
The Bronzeville shelter houses 260 residents who are majority U.S. citizens, according to Caryl West, the executive director of Bright Star Community Development Corporation.
Along with the federal activity in front of the homeless shelter in Bronzeville where four people were detained, agents also detained two people outside a homeless shelter in the Northwest Side neighborhood of Budlong Woods.
Notably, a ruling by the U.S. Supreme Court last year made it legal for local governments to criminalize homelessness. The move puts a target on an already vulnerable population, which, in Chicago, is disproportionately Black. This is something that Kobi Guillory said activists have been warning about.
“We’ve been saying for the longest time that it was bound to happen in every community, in every oppressed community,” said Guillory, chair of the neighbor committee with the Chicago Alliance Against Racist and Political Repression.
“We were always going to experience the attacks; they don’t care if you were born in this country, if your ancestors were brought here in shackles in the 1700s, it doesn’t really matter to them,” Guillory explained, “because to them, the only people that they actually care about are rich, white people – rich, white men specifically.”
South Chicago resident Denver Blaine and Woodlawn resident Alexis Barker work in Bronzeville near where the raid took place. Blaine, 23, said she thinks incidents like what happened in South Shore and East Garfield Park will help to make people more empathetic.
“I think a lot of people at first thought that it wouldn’t come to this, but I think now everybody’s seeing that they’re not targeting just illegal immigrants. They’re targeting people that they don’t want to be here, period,” Blaine said.
Barker said that the incidents have opened her eyes to the corruption in the country.
“It really makes you feel like, wow, this place is really corrupt, it’s very alarming. It makes you more aware. It makes you want to know what’s going on, because things can switch up so quick,” Barker said.
History shows that Black Americans have long been targeted by the federal government. The FBI counter-intelligence program, COINTELPRO, was created to quell Black activism movements such as the Black Panther Party and civil rights leaders like Dr. Martin Luther King, Jr. The Chicago Police Department worked alongside the FBI to murder Illinois Black Panther Party Chairman Fred Hampton while he was sleeping in his Chicago home in 1969.
Though history shows that Black people have always been the target of police and federal activity, Guillory said, Black people believing they would be safe from Trump’s immigration enforcement is a result of propaganda promoting divisiveness between oppressed communities.
“I think this escalation on the federal level is also an escalation of the police brutality that has been happening to Black communities for centuries,” Guillory said. “That escalation is also a teacher. That escalation is also showing people what the reality of the police action is: They’re not here to serve and protect, they’re here to repress Black and brown communities.”
Clarification: This story has been updated on Oct. 9 to clarify the types of inspections that did and did not take place at 7500 S. South Shore Dr.
