'A lot of targets to go after': Chicago ICE field director talks immigration efforts, response to recent raids
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CHICAGO (WGN) – Waves of protests and public outcry have surged nationwide in response to actions taken by U.S. Immigration and Customs Enforcement (ICE) involving operations and raids.

On Monday, WGN TV News reporter Courtney Spinelli interviewed Sam Olson, the field director of ICE’s Chicago office, about the recent local immigration enforcement efforts. The discussion covered topics such as the individuals being reportedly targeted in these operations and how the agency is addressing the protests against its activities and those endorsed by President Donald Trump’s administration.

It’s likely that the Chicagoland area could experience increased immigration crackdowns, influenced by ongoing discussions between local, state leaders, and the President.

Trump has promised ICE will expand immigration crackdowns and the number of deportations following nationwide ‘No Kings’ protests Saturday. He specifically took aim at Chicago and other Democrat-led sanctuary cities.

When asked what Chicago ICE officials have been directed to do and what people can expect to see, Olson said officers will be in the streets, seven days a week, working to enforce immigration law.

“We have, unfortunately, a lot of targets to go after. There’s a lot of people who are here, that are here illegally with criminal convictions, here with final orders of removal and our officers are out there daily,” Olson said.

Announced by the White House last week, ICE arrests have topped 100,000 under Trump, and border czar Tom Homan claimed things would not be slowing down, with workplace immigration enforcement set to “massively expand.”

Recent ICE arrests at locations in Chicago and Broadview, among other places, have led to protests and outrage.

In early June, at least 10 people were detained after they received texts telling them to come to a check-in appointment at a South Loop building of a government contractor that operates the Intensive Supervision Appearance Program (ISAP) for inmates, using ankle bracelets and other monitoring devices as an alternative to detention. On Father’s Day, a similar scene unfolded in Broadview, also at an ISAP office, as at least three people were detained after receiving texts.

In both cases, activists pushed back against the actions of ICE officers, protesting the arrests and demanding the release of detainees. Some local activists, including city council members, claimed people were illegally detained.   

In some cases, family members told WGN TV News that despite regular check-ins with immigration officials, their family members did not know of an order of removal against them until they were in handcuffs.

ICE officials claim there is more to the story and anyone who was taken into custody during ISAP check-ins was detained for a reason.

Spinelli: “Border czar Tom Homan initially said it was a priority to go after dangerous criminals, but we have seen some examples, like the enforcement and detentions at ISAP check-ins, people who activists claim were not doing anything wrong, that were already under supervision. What’s the response to that, and why now with those folks that may not have a criminal history?” 

Olson: “With immigration, like I said, there’s a lot of people that we have the ability to target; our authorities are kind of wide-ranging. While we’re focusing on a lot of the criminals, there are a subset of those who are here illegally that have final orders of removal that were maybe on some type of reporting procedure, but at some point, they’ve already been already ordered removed by a judge, so again, we’re just enforcing that order.” 

Spinelli: “What you’re saying is, the folks that were taken into custody that were detained, all would have had an order of removal, and not just following the asylum process and doing what they were asked to?”

Olson: “Correct, because there’s people that checked in that we did have to arrest because they had an order of removal and no impediments to that removal, and there’s other folks that did check in that had stays or that they had, you know, something else that made them essentially not removable at this time, and those are the ones we didn’t take action on because the case just isn’t finalized yet.”

Some who emerged from the ISAP office in either case were fitted with electronic monitors, while others were given additional requirements to appear at upcoming appointments.

Chicago ICE officials claim they have been seeing an increase in heightened tensions against their officers, specifically while carrying out enforcement.

“I’m all for people protesting and using their first amendment rights to do that, but when it kind of crosses that line into impeding the officers that there’s assaulting the officers, that’s the part that’s very frustrating, because again, they’re on this mandate to do; they have this job to go out and enforce the law, and a lot of times, the law tells us that we shall take these people into custody because of a statute,” Olson said.

Olson was asked whether people who have no orders of removal need to be worried, especially if they are being notified of ISAP check-ins.

“I can’t tell people how to be worried, the idea is that everybody probably knows what their status is in the U.S.,” Olson said. “If you’re here without status, but you’re going through a process, the issue is we’re not going to remove somebody who is not amendable to removal, right, we have to follow that law, how we do these removals.

“These aren’t just snatching somebody off the street and then they’re on the plane four hours later. There are checks that we go through.”

ICE also shared information on two recent arrests, which sparked backlash among leaders and neighbors in the city’s Pilsen neighborhood earlier this month.

Reports in early June indicated an alleged ICE raid led to the arrest of two people from Mexico.

“We are, right now, investigating the reason why those neighbors have been detained without a warrant,” Ald. Byron Sigcho-Lopez (25th Ward) said at the time. “In both instances, the video footage and the witness’s recollection, there was no warrant.”

A spokesperson for ICE shared a statement on the arrests:

Jose Juan Rueda-Diaz, 35, is a citizen of Mexico previously convicted in Cook County for aggravated unauthorized use of a weapon, and by the U.S. District Court Tucson, Arizona, of illegal entry. Rueda, a known member of the Party Players street gang, has also been arrested by Chicago Police Department multiple times for offenses to include reckless conduct, assault, and parole violation. An immigration judge ordered Rueda removed from the United States in 2012, and he has been previously removed to his home country twice in the same year.

Fisel Pablo Morales, 28, is a citizen of Mexico arrested at the same time as Rueda. When arresting personnel attempted to question Morales, he fled, resulting in a foot chase. Once apprehended, Morales gave consent for his place of residence to be searched where Rueda was ultimately arrested. As Morales is a foreign national with no evidence of lawful admittance into the U.S. he was arrested in accordance with the Immigration and Nationality Act.

Though a warrant was provided to Rueda once it was safe to do so, U.S. immigration officers have authority to interrogate, without warrant, any alien or person believed to be an alien concerning his or her right to be, or to remain, in the United States. It is under this authority that Morales was arrested.

States with laws that prevent local authorities from working with ICE suffer the most harm from criminal aliens. An immigration detainer was placed on Rueda while in local custody, which was not honored. When there is no cooperation with federal law enforcement, public safety is placed at risk.

According to Illinois statute, local law enforcement is typically restricted from participating in civil immigration enforcement, including honoring ICE detainer requests.

Cook County court records show Rueda was on probation after pleading guilty in a September 2024 case for aggravated unlawful use of a firearm involving a vehicle and the absence of a Firearm Owner’s Identification Card (FOID). He initially entered a not guilty plea in Oct. 2024 and changed his plea to guilty in May 2025.

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