The real story behind the midnight immigration raid on a Chicago apartment building

Federal agents raided this apartment building in Chicago’s South Shore neighborhood, claiming it was occupied by the Venezuelan gang Tren de Aragua. (Jim Vondruska for ProPublica)

by Melissa Sanchez and Jodi S. Cohen for ProPublica

For months, the Trump administration has justified its dramatic midnight raid on a Chicago apartment complex by saying that it had intelligence that the violent Venezuelan gang Tren de Aragua had taken over the building. But officials have provided no evidence to back up the claim.

Now, new documents confirm in the government’s own words that what prompted the raid was more pedestrian: allegations that immigrants were squatting in the complex. And the landlord had given federal officials, who were already targeting immigrants in Chicago, the blessing to search the building.

Arrest records for two of the 37 immigrants detained that September night, included in a motion filed Tuesday that’s tied to an ongoing federal consent decree, provide the clearest picture yet of what led to the controversial and aggressive operation, in which agents descended from a Blackhawk helicopter, broke down doors and zip-tied U.S. citizens and immigrants.

The records reveal that agents entered and searched the complex with the “owner/manager’s verbal and written consent.” Agents wrote that they launched the operation “based on intelligence that there were illegal aliens unlawfully occupying apartments.” They said they focused their search on units “that were not legally rented or leased at the time.” That narrative appears word for word in both arrest reports — for a Venezuelan man and a Mexican man.

“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 that led to the consent decree. “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 makes no mention in the records of Tren de Aragua, even though officials repeatedly cited the gang’s presence in the building as the motivation for the raid. Agents paraded immigrants in front of cameras and called their arrests a victory against terrorism. The government also claimed two of those arrested were gang members but never provided any proof.

ProPublica previously reported, based on interviews and records, that there was little evidence to back up the government’s claims. Even today, four months after the raid, federal prosecutors have not filed criminal charges against anyone who was arrested.

Over the past few months, ProPublica has interviewed 15 of the immigrants detained that night; all denied gang membership. They and others who lived in the building acknowledged there was criminal activity there, including the murder of a Venezuelan man last summer, but nobody knew of gang members there.

The two arrest records were filed in federal court as part of ongoing litigation over whether the government, during its monthslong deportation campaign in Chicago, violated a 2022 consent decree that limits warrantless arrests. The consent decree is still in place, and the government continues to challenge it.

Government attorneys had previously acknowledged in court that hundreds of immigrants detained last year may have been improperly arrested.

Following a court order, DHS has been providing administrative arrest records to attorneys who now are demanding the release of some of those immigrants from custody or the removal of restrictions for those who are already out. That includes the Venezuelan man and Mexican man taken during the raid.

In the motion filed Tuesday night, immigrant rights attorneys said that to justify warrantless arrests across Chicago, the government described immigrants as flight risks though they were not. Some of the factors that DHS used to make that determination for the South Shore men — including their “willful disregard for other’s personal property” and their “attempt to flee from law enforcement” — were baseless and contradicted by the arrest narratives, the attorneys wrote.

Even more of the 37 arrests that night may have violated the consent decree, attorneys said, but the cases under review are for those who remain in the U.S. As the weeks and months passed, most of the immigrants detained in the South Shore raid were deported or gave up on their efforts to stay in the country.

The property owner, Trinity Flood, a Wisconsin-based real estate investor, and the management company at the time of the raid, Strength in Management, did not immediately respond to requests for comment on Wednesday morning. Flood and Corey Oliver, the management company’s owner, have repeatedly declined interview requests and have not acknowledged any involvement in the operation.

A DHS spokesperson did not respond to questions Wednesday morning but repeated earlier statements that the raid was performed legally. “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,” the spokesperson said.

From the beginning there had been questions about whether Flood and her property manager tipped off the government to get rid of squatters in her building, which had repeatedly failed city inspections in the two years before the raid.

Last month, state officials launched a housing discrimination investigation into allegations that Flood and Strength in Management used federal agents to illegally force the Black and Hispanic tenants from the 130-unit building in Chicago’s South Shore neighborhood.

In their complaint, state officials wrote that “building management blamed Venezuelan tenants for their own (management’s) failure to provide needed locks and security service, as well as other needed maintenance and repairs, and perpetuated stereotypes about Venezuelan gang members to send a message that tenants born outside of the United States were considered gang associates, even if they were law abiding.”

Within hours of the raid, workers from the management company were tossing tenants’ belongings in the trash and clearing out apartments, the complaint states.

State officials said that they could not provide any additional information on an ongoing investigation, but that they look forward to a response from Flood and Strength in Management.

Several Venezuelan immigrants detained that night said they were angry to learn that the building’s owner and property manager had facilitated federal agents’ entry. “We were paying our rent, doing things the right way,” said Jean Carlos Antonio Colmenares Pérez, 39. “Then suddenly, boom, the government comes in and takes us out. I don’t understand.”

Colmenares spent more than two months in federal custody before he was deported in December.

“They took us out as if we were dogs. As if we were criminals,” said his cousin, Daniel José Henríquez Rojas, 43.

Henríquez was detained for about two months before he was deported. Federal agents also took his wife and then-6-year-son that night and later transported them to a facility in Texas where they were detained for about a month. The family is now back together in Venezuela.

Johandry José Andrade Jiménez, 23, had moved into the South Shore complex with his wife and three young daughters just two days before the raid. Andrade was deported in December. His wife was released with an ankle monitor in Chicago, where she now struggles to support their daughters alone.

“They separated me from my family,” Andrade said. “I feel awful.”

The complex was home to dozens of mostly African American and Venezuelan tenants. While some said they had stopped paying rent because of the dangerous and dilapidated conditions, close to a dozen Venezuelans, including Colmenares, Henríquez and Andrade, told us they were paying rent to people they believed worked for the management company.

But in some cases, that money was going to other tenants who claimed to be the managers. ProPublica interviewed a U.S. citizen who said that he and others moved Venezuelan families into empty units, charged whatever amount they believed was fair and pocketed the money. “We started making them pay rent to us,” the man said.

Flood, who is facing a foreclosure lawsuit, said in court records last fall that her company had invested millions of dollars to repair and maintain the building and on legal fees for evictions. Weeks before the raid, the company obtained court orders to evict squatters.

The building continued to deteriorate after the raid. Oliver testified in court that he briefly hired security people but then fired them after they didn’t do their jobs. In November, a county judge ordered that another company take over management of the building and required that the remaining residents move out.