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One man said he was awakened to the sound of helicopters outside his South Shore apartment building before four masked federal agents allegedly burst through the door and beat him with a rifle in front of his wife and three young daughters.

Another man claimed he was still in bed when a large black police dog clamped down on his leg and he was allegedly zip-tied by agents. Others said agents threatened to kill them, and allegedly forced them outside into vans in their pajamas and underwear, and took them to detention facilities without due process.

No one ever saw a warrant, they said.

The harrowing stories were included in a series of federal tort claims filed Wednesday by immigration advocacy groups on behalf of 17 residents who were arrested illegally and allegedly brutalized in a controversial overnight raid in a South Shore apartment building during Operation Midway Blitz last fall. Another person who submitted a claim had also lived in the building and had been arrested there in the days leading up to the raid.

The tort claims, a prerequisite to a lawsuit against the federal government, foreshadow what would be the first litigation filed in connection with the military-style immigration enforcement raid at 7500 S. South Shore Drive that unfolded in the middle of the night with helicopters, snipers and bright spotlights.

The filings allege federal agents stormed the U-shaped building in the dead of night on Sept. 30, broke down doors without warrants and rounded up adults and children alike at gunpoint. As it unfolded, a Department of Homeland Security camera crew filmed footage that was later posted to government social media accounts as promotional content.

The claims were filed by the Mexican American Legal Defense and Educational Fund, the MacArthur Justice Center, the Immigration Clinic of the University of Chicago and the National Immigrant Justice Center.

“This raid is among the most abhorrent actions of Operation Midway Blitz, part of the current administration’s militarized campaign targeting communities of color in cities across the country,” said Susana Sandoval Vargas, MALDEF Midwest regional counsel. “We are pleased to represent courageous clients who have decided to stand up against this abuse of power and hold the federal government accountable for its actions.”

Each of the 18 claimants is seeking about $5 million in damages for alleged emotional distress, lost wages and items lost due to the unlawful raid, including immigration documents, money and personal effects. Two are U.S. citizens, while the rest are immigrants.

A DHS spokesperson provided a statement contending legitimate arrests were made and that two confirmed gang members were found there.

“No children were handcuffed or restrained during this operation. For their own safety and to ensure were not being trafficked, abused, or otherwise exploited — children found with those arrested, including a (gang) member, were taken into custody until they could be put in the care of a safe guardian or the state,” the statement read.

“This operation was performed in full compliance of the law. 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 filings document the first-hand experiences of many who were arrested that day.

One of them, Johandry José Andrades Jiménez, said he was asleep with his wife and three daughters aged 3, 1 and 6 months, when they were awakened by the sound of helicopters and he saw armed men dressed in military uniforms gathered outside.

“Within a few minutes, agents approached Mr. Andrades Jiménez’s door,” the declaration submitted on his behalf stated. “Agents were yelling aggressively, ‘Open the door! Get out! Get Out!’ Agents hit the door forcefully twice and breached the door. Four large men armed with guns then entered the apartment.”

Andrades Jiménez said one agent allegedly ordered him to get on the floor “or I’ll kill you.” He was then struck in the head with a rifle and thrown to the floor “in front of his wife and children, who were crying,” the declaration stated.

The agents allegedly zip-tied Andrades Jiménez and asked him if he was a member of the Venezuelan gang Tren de Aragua, which he denied, according to the declaration.

Battered and shirtless, Andrades Jiménez was marched out of the building and separated from his family. He was taken to the ICE detention facility in Broadview and eventually transferred to other jails in several states, where he was denied access to heart medication over more than two months while in custody, according to his declaration.

Other declarations included in the filings indicate federal authorities had geared up for the raid weeks in advance.

One affiant, identified as J.M. Jiménez, said about a month before the raid, federal agents allegedly disguised as utility workers were going door to door marking the doors of Hispanic-occupied apartments with a big “X.”

The raid, which was led by then-Border Patrol Cmdr. Greg Bovino, was one of the most shocking episodes during the Trump administration’s Operation Midway Blitz, which resulted in the arrests of thousands of immigrants and numerous clashes with citizens on city and suburban streets throughout the fall and early winter.

The assault on the building in a majority Black neighborhood on the city’s South Side was widely condemned, and the Illinois Department of Human Rights earlier this year launched an investigation into the owner’s role. The state has alleged that the owner prompted the September raid by telling the federal government there were Venezuelan immigrants living in the complex who were “unauthorized occupants and had threatened other tenants.”

Though the Trump administration often justified their deportation operation by claiming to pursue people who posed a safety risk to the public, no criminal charges were filed against anyone in connection with the raid, either in U.S. District Court or in Cook County.

DHS had previously said the raid was the result of federal criminal warrants, though none were made publicly available. Two immigrants who were detained in the raid had no felony criminal record or presented any flight risk, yet were improperly subjected to “warrantless arrest,” according to a federal judge who reviewed allegations of warrantless arrests by agents.

Building residents continued to face problems in the weeks and months following the raid. They formed a tenant union after a Cook County judge appointed a third-party receiver to manage the property and ordered the building to be vacated.

Among the claims in the tort filings Wednesday were Norelly Eugenia Mejías Caceres and her partner, Daniel José Henríquez Rojas, who lived with her 6-year-old son on the second floor of the building.

Twice before the raid, “unfamiliar men in green vests knocked on” Caceres’ door. The first time they came, the men looked into her apartment, asked about the lights and left, their declaration alleged. She did not open the door the second time, but suspects they were investigating who lived in the building.

On the night of the raid, Caceres and Rojas were awakened by the sounds of a helicopter and saw agents rappelling down onto the building. She tried not to awaken her child because she did not believe the agents would enter her apartment, the declaration said.

Suddenly, 20 agents allegedly smashed the front door, entered the bedroom, pointed military-style guns and shouted “Get out!” and “Go downstairs” at the family. Agents told her not to record with her cellphone and did not produce a warrant, she said.

Caceres attempted to explain that they had pending asylum cases but were told to get out and they were prevented from showing their documents. The adults left barefoot and the child was shirtless in his underwear because they did not have time to get changed, the declaration said.

The declaration alleged Rojas was zip-tied in the hallway and Caceres fainted. Caceres said the agents placed a hot metal object on her chest that left a bruise and the agents carried her by her wrists and ankles down the hallway, the declaration said. They used a large towel to carry her down the stairs, according to the allegations.

As she sobbed, she asked the agents where her child was but was told to look into a camera, which agents used to identify her, the declaration said.

Caceres “complied with the agents’ commands, but she had been sobbing so intensely that the agents told her she needed to open her eyes wider for the smartphone camera,” the declaration said. “Once she complied, the agents took a photo of her face with the smartphone. The agents then called (Caceres) by her full name and identified her birthplace as Venezuela.”

After she confirmed this, the agents told her that her child was with Rojas, she said. The child was wrapped in an aluminum blanket but not wearing a shirt or shoes, the declaration said.

Caceres, her son and Rojas were taken to a detention center where the adults were separated from each other. Caceres was taken to a detention facility in Texas where “the bathrooms were overcrowded and unsanitary, and (the child) once cut himself on a rusty bathroom door,” the declaration said.

Caceres and her child signed a form agreeing to be returned to Venezuela and was deported in late October. They did not reunite with Rojas until he was deported in late November, the declaration said.

Another woman, whose name was redacted, was living in the building and also described men coming by her apartment posing as repairmen, according to the declaration. On the night of the raid, she was also startled awake by the helicopter and drones, then watched as agents rappelled onto the roof and landed directly outside the open window of her living room.

She could hear agents breaking their way into other apartments and became “very afraid,” the declaration said.

She asked agents not to break down their door, but they did it anyway, the declaration said. Her son had what she believes to have been an anxiety attack during the raid, she said, as agents searched through their apartment and allegedly pointed guns at them. The agents forced her and her son out of the apartment into another on the second floor, where she witnessed agents “beat several detainees in the living room,” the declaration said.

One agent allegedly hit a man with what appeared to be the butt of a rifle and another man was kicked by agents in a circle, the declaration said. The child hyperventilated and was put into a separate bedroom where he could still hear. Federal agents zip-tied the woman and her son, according to the declaration.

A declaration from another resident alleged agents entered an apartment where four children lived, pointed guns and zip-tied a man, even as he cried that the restraints were too tight. The family was allegedly led out of the building at gunpoint, still wearing their pajamas and the man was taken to the ICE processing center in Broadview. There, he asked agents why he’d been arrested.

He was told “he and his neighbors were part of Tren de Aragua,” the declaration said.

This story has been updated to reflect the correct name of the Mexican American Legal Defense and Educational Fund.