Exclusive | Chicago raids expose how leftist groups help criminals evade ICE: ‘Coached to fight back’

CHICAGO — It was still dark and cold at 5:30 am Thursday when teams of US Immigration and Customs Enforcement (ICE) officers hit the streets on “targeted enforcement” missions to arrest criminal illegal migrants.

They call them “the worst of the worst.”

The Post embedded with one team of federal ICE agents who admitted the task of identifying criminal migrants in the sanctuary city – which orders its local law enforcement not to help them – and actually making arrests can be like finding needles in haystacks.

Further complicating matters, local activists, legislators and school administrators in Illinois have been coaching migrants, including criminals charged with sex assaults, weapons violations and worse, on their rights and how to evade ICE agents. Even those detained were fairly brazen.

On Thursday, between 10 teams of about 10 agents each, ICE made only two arrests in Chicago after five hours on the ground.

The Post witnessed Diego Antonio Montero, 24, a Venezuelan national who crossed illegally into the US in May 2023 as he was arrested and put into a caged van by ICE agents.

He was calm and composed and told ICE in Spanish he was not a criminal and was confident he’d go before a judge and be set free.

His record shows otherwise. Chicago police had previously arrested him for criminal trespass, battery, and aggravated assault with the use of a deadly weapon. All charges are pending before the Circuit Court of Cook County, Illinois. An arrest warrant was issued on April 22, 2024, but not honored.

“Sometimes it’s a very uphill battle,” officer Sam Olson, a nearly 25-year veteran of ICE, told The Post as he drove to the first target.

“We have their information because they were previously arrested and booked in and fingerprinted somewhere, therefore we know they are here. But it’s not as if we are getting notification if these criminal aliens are arrested. Nobody local will tell us that.”

Montero was also on the run from Homeland Security. After he skipped out on a 2024 immigration hearing, a judge ordered him removed from the US.  

Last August, ICE officers encountered Montero and arrested him. He was detained until November 7, 2024, then released into the Alternative to Detention Program with a GPS tracking device. ICE picked him up Thursday after locating him via his ankle bracelet.

ICE agents, who have been joined by agents from the DOJ, FBI and ATF as a result of Trump and new Border Czar Tom Homan’s demand for more arrests, call what they do in their early morning trips “knock and talks.”

They arrive at a target’s home or apartment at 6 a.m. or after as they are not allowed to knock before that time.

But at two stops in the Humboldt neighborhood, the targeted residents in the homes where ICE knocked, knew not to open the door.

Instead, at one house three people gazed down from an upper floor window – seemingly unfazed by the presence of armed agents in bulletproof vests and loud walkie-talkies knocking repeatedly at the front and side doors.

After about 10 minutes of stalemate, ICE gave up and returned to their vehicles to go to their next scheduled stop.

ICE officers rarely obtain warrants from federal judges for their “knock and talks” and can only arrest their targets if they open the door.

Olson made clear his team is not picking up the wives or girlfriends of the criminals they are targeting. The Post saw ICE agents talking gently to one girlfriend of a man they attempted to detain to explain why they were there.

Organizations in Illinois like Catholic Charities, La Voz Latina and school administrators are holding workshops and making flyers and videos explaining to illegal migrants what their rights are, and how to evade ICE.

“I do not wish to speak with you, answer your questions or sign or hand you any documents based on my 5th Amendment rights under the United States Constitution,” reads text on cards being distributed in Chicago and elsewhere in the state.

According to the city’s “Welcoming Letter,” “We have a responsibility to provide access to shelter, food, and medical care to everyone, regardless of immigration status.

“Many of our new arrivals have walked hundreds of miles, navigating great danger through multiple countries, in pursuit of safety and opportunity in the United States. We are committed to assisting each family and individual, providing human services with respect and dignity.”

Chicago police are prohibited from questioning, arresting or prosecuting “individuals solely on suspicion of being undocumented,” according to the city office of Immigrant, Migrant or Refugee Rights.

“Sanctuary cities like Chicago are making it very difficult,” Homan, former head of US Immigration and Customs Enforcement, told the Post Friday. “I call everything they’re doing ‘How to Escape ICE.’ But we’re fighting back.

“We have some plans in the pipeline that are going to increase our chances of making it easier for ICE to make more arrests. As it is, having all these teams out and with help from the ATF and other agencies is like a force multiplier. Our guys are doing a great job and we aren’t going away.”

There are at least 11 million people living in the US without legal status, with 77 percent having lived here for five years of more, according to the most recent census figures.

“I sympathize with the ICE agents stuck working in Illinois because their backs are really up against the wall,” Terry Newsome, a local longtime activist and host of the “Behind Enemy Lines” podcast, told The Post.

“They have to aggressively find these individuals who are being coached to fight back and what to do to keep from being arrested. Even [Venezuelan criminal gang] Tren de Aragua are being coached by the radical Illinois Democrats on how to avoid ICE.

“The citizens of Illinois have to fight against the sanctuary city and state and demand they put the citizens of Illinois before the criminal illegal aliens that have flooded our communities.”

President Trump has promised mass deportations of “millions” in the country illegally.

But celebrities such as Selena Gomez and Democratic pundits have unfairly characterized ICE as the bad guys, out to raid and arrest terrified families — the reality on the ground in Chicago was very different.

“Our mission is targeting the worst of the worst,” said the soft-spoken Olson, who said one of the toughest parts of his job is seeing ICE officers portrayed as heartless Nazis.

“We’re people from the community ourselves,” Olson said. “We want the community to be safer for everyone, including our families — and we are only upholding the Constitution and enforcing the laws Congress has mandated while putting our lives on the line daily.”

Olson said the money and manpower needed to track down each criminal migrant is huge — even though they are in the country illegally.

“We have very smart officers doing constant and incredible research before we can even get to the point of going out to find people,” he said. “The amount of hours that go into just one case are unbelievable.”

Though ICE was able to arrest Montero at their last stop, they had to let two other migrants go after first cuffing them.

Olson said while they had criminal backgrounds, they had also applied for asylum and were out on bond and therefore immune from arrest.

But Olson was cheerful enough as his van pulled back into the parking lot near the ICE offices in a gritty, industrial area of downtown Chicago five hours after the teams set out. He is careful to avoid any discussion of politics and declined to speak about the change in administration from Biden to Trump.

“We’re doing what we are mandated to do and we are confident we’re going to make more and more progress,” Olson said. “I hope people realize someday that this is all about upholding the law and making the country safer — but our job will continue no matter what misconceptions people have about us.”