Chicago ICE Raid Rooted in Squatter Allegations, Not Terrorism Fears
A dramatic midnight raid on a Chicago apartment building in September 2025, initially touted by the Trump administration as a victory against terrorism and the Venezuelan gang Tren de Aragua, was in fact prompted by allegations that immigrants were unlawfully occupying apartments in the complex, according to newly released government documents. The revelation, reported by ProPublica, casts serious doubt on the administration’s public justification for the aggressive operation, which involved agents descending from a Blackhawk helicopter and forcibly detaining 37 individuals.
The documents reveal that federal agents entered and searched the building with the “owner/manager’s verbal and written consent,” focusing on units “that were not legally rented or leased at the time.” Arrest reports for a Venezuelan man and a Mexican man, included in a motion filed Tuesday tied to an ongoing federal consent decree, contain identical narratives stating the operation was “based on intelligence that there were illegal aliens unlawfully occupying apartments.”
“It was a brutal lie against the American public,” said Mark Fleming, an attorney with the National Immigrant Justice Center and co-counsel in a lawsuit against the government. “This was really about immigrants purportedly occupying apartments unlawfully, which is radically different than the story they told.”
The U.S. Department of Homeland Security has not mentioned Tren de Aragua in connection with the raid, despite repeatedly citing the gang’s presence as the primary motivation. Agents reportedly paraded those arrested in front of cameras, claiming the arrests were a win against terrorism and initially asserted that two of those detained were gang members – claims for which no proof was ever provided.
The raid occurred at a building located at 7500 S. South Shore Drive in Chicago, Illinois. ProPublica’s earlier reporting, based on interviews and records, found little evidence to support the government’s claims regarding the gang’s involvement. As of today, , four months after the raid, federal prosecutors have not filed criminal charges against anyone arrested during the operation.
Interviews conducted by ProPublica with 15 of the immigrants detained during the raid revealed that all denied any affiliation with Tren de Aragua. While acknowledging some criminal activity in the building, including a murder last summer, none reported knowledge of gang members residing there.
The documents surfaced as part of ongoing litigation concerning whether the government violated a 2022 consent decree that limits warrantless arrests during its deportation campaign in Chicago. Government attorneys have previously acknowledged in court that hundreds of immigrants detained last year may have been improperly arrested. DHS is currently providing administrative arrest records to attorneys, who are now seeking the release of those still in custody or the removal of restrictions for those already released, including the Venezuelan and Mexican men arrested during the South Shore raid.
Attorneys argue that the government improperly described immigrants as flight risks to justify warrantless arrests, citing factors like a “willful disregard for other’s personal property” and an “attempt to flee from law enforcement” that were contradicted by the arrest narratives. They suggest that more of the 37 arrests may have violated the consent decree, focusing on cases where individuals remain in the U.S.
The property owner, Trinity Flood, and the management company at the time of the raid, Strength in Management, have not responded to requests for comment. Flood and Corey Oliver, the management company’s owner, have repeatedly declined interview requests.
A DHS spokesperson reiterated previous statements that the raid was performed legally, stating, “Given that two individuals of a Foreign Terrorist Organization were arrested, at a building they are known to frequent, we are limited on further information we can provide.”
Questions arose from the beginning regarding whether Flood and her property manager alerted federal authorities to address squatters in the building, which had repeatedly failed city inspections in the two years prior to the raid. A state housing discrimination investigation was launched last month into allegations that Flood and Strength in Management used federal agents to illegally force Black and Hispanic tenants from the 130-unit building.
State officials allege that building management blamed Venezuelan tenants for their own failures to provide adequate security and maintenance, and perpetuated stereotypes about Venezuelan gang members. Workers from the management company were reportedly seen discarding tenants’ belongings and clearing out apartments immediately following the raid.
Several Venezuelan immigrants detained during the raid expressed anger upon learning that the building’s owner and property manager had facilitated the federal agents’ entry. Jean Carlos Antonio Colmenares Pérez, 39, stated, “We were paying our rent, doing things the right way. Then suddenly, boom, the government comes in and takes us out. I don’t understand.” Colmenares was deported in December after spending over two months in federal custody.
His cousin, Daniel José Henríquez Rojas, 43, echoed this sentiment, stating, “They took us out as if we were dogs. As if we were criminals.” Henríquez was also deported after approximately two months in detention. Federal agents also detained his wife and then-6-year-old son, who were held in Texas for about a month before being reunited with the family in Venezuela.
Johandry José Andrade Jiménez, 23, had moved into the complex with his wife and three young daughters just two days before the raid. He was deported in December, leaving his wife and daughters in Chicago. “They separated me from my family,” Andrade said. “I feel awful.”
The building housed a mix of African American and Venezuelan tenants. While some had stopped paying rent due to the building’s condition, nearly a dozen Venezuelans confirmed they were current on their rent payments to individuals they believed were associated with the management company. In some instances, these payments were reportedly being collected by other tenants who falsely presented themselves as managers.
Flood, currently facing a foreclosure lawsuit, stated in court records that her company had invested millions in repairs and legal fees for evictions. Weeks before the raid, the company had obtained court orders to evict squatters. Following the raid, the building continued to deteriorate, and a county judge ultimately ordered another company to take over management and require all remaining residents to move out.
