Chicago under siege

by the federal government

This Substack is usually about finding joy, but avoiding misery is often a more important part of human flourishing—I’m simply lucky that I can mostly focus on the joy part. We currently have a government that is intent on causing misery to a large part of our community, and so I must talk about it.

For this post, I’ve suspended the usual format of a short update in front and a music section at the end. Hoping to be back with regular programming soon.

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The most disconcerting things in Chicago since September are the amount and the nature of immigration enforcement activities in the area—called Operation Midway Blitz by the government—and how any kind of pushback against them has been handled. Another disconcerting thing is that, depending on the neighborhood you’re in and who you know, you could live your life mostly as before, not being aware of much of it.

There are 2 great recent blog posts on this:

1. What I Need You To Understand, Notes from Chicago in Late October by Dan Sinker is more evocative, getting at the feeling of living here right now. Check out the “A couple places to give your time and your money” section if you want to do something.

2. Dispatch from Occupied Chicago by Laurie Merrell¹ is more analytical, talking about different aspects of the experience. She starts with a “What is happening” section where she summarizes the events over this period.

I want to spend a bit more time on the actual events. As I said at the start, even some people who live in the area are not aware of much of what’s actually happened so far. And I’m certain that, simply based on how I found out about so much of this², most people who don’t live here have little idea of what’s happening.

I also want to stress that so much of this is unacceptable. Most of the events I highlight here, even individually, should be a scandal, regardless of your political position on immigration in general and on what we should do about immigrants who are here already.

Something to note before we start: the 2 major players in this operation are Immigration and Customs Enforcement (ICE) and Customs and Border Protection (CBP), which includes the Border Patrol. They are both part of the Department of Homeland Security (DHS) and are coordinating with each other, but they are 2 separate agencies. Even though there’s a common misconception that all of this is done by ICE—the acronym is so catchy—many of the most egregious incidents here involve CBP, and the commander of Operation Midway Blitz is Greg Bovino, who is part of CBP.

I’ll first highlight the 3 events that stand out for their severity or scale, then talk about a few recurring themes in other incidents.

Killing of Silverio Villegas González in Franklin Park (9/23)

ICE agents made a traffic stop in the suburb of Franklin Park, near O’Hare Airport, and as Silverio Villegas González, the stopped driver, tried to flee, they shot and killed him. He had just dropped off his two kids and was headed to work.

As discussed in the first link, the federal government provided a description of this incident that does not match video evidence that’s already out in the public. And contrary to the government’s claims, Villegas González had no criminal history—only traffic violations that were not crimes³. The supposed justification for the shooting, that the agent feared for his life, is hard to square with the evidence.

South Shore raid (9/30)

By far the largest single incident was a midnight raid on an apartment building in the South Shore neighborhood. Agents stormed the building, using helicopters and flashbang grenades.

federal agents detained nearly every resident of the 130-unit building—including children and babies—placing them in zip ties and separating them by race into vans for more than two hours early Tuesday morning.

While there were many Venezuelans⁴ living in the building⁵, many of the people who were detained were black US citizens.

This next quote from the Border Patrol leader Greg Bovino shows how little respect he has for people’s rights:

In an interview with NewsNation, U.S. Chief Patrol Agent Gregory Bovino said that U.S. citizens were also detained during the raid due to safety reasons, saying “we generally don’t determine alienage while in the building,” adding, “no rights have been violated today.”

Border Patrol shoots a woman in Brighton Park (10/4)

From early on in Operation Midway Blitz, rapid response teams started to form in neighborhoods across the area, for the purpose of documenting immigration enforcement activity and warning area residents⁶. On October 4, such a rapid response team was following Border Patrol agents in the Southwest Side neighborhood of Brighton Park, when there was a minor car crash between the Border Patrol vehicle and two from the rapid response team, an agent got out of the vehicle and shot Marimar Martínez, one of the drivers who were following the agents, multiple times. Martínez escaped the scene and was able to get to the hospital. Based on the article, this easily could have been another person shot dead by immigration officers in the area.

Martínez is being charged with felony assault of a federal officer, for allegedly driving into the Border Patrol vehicle. Her lawyer claims that the body-cam footage contradicts this narrative. We will hopefully find out during the trial, but another instance of the government being less than trustworthy here is that the agent who shot Martínez drove the vehicle that was involved in the incident to Maine, before the defense team had a chance to inspect it.

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And here are some themes. (Update 2025-11-10: I’ve added a couple of important updates in the week after I published, but you should not take this as the most up-to-date version going forward):

Lack of accountability

This is the major theme that underlies everything else, and explains a lot of why the community is so fiercely against the immigration officers operating in the area.

If you were about to be detained by law enforcement, you expect certain things. You expect to know who you’re being detained by, and why. If officers try to detain you in public without a warrant, there needs to be probable cause for them to believe that you are committing a violation—that comes from the 4th Amendment.

During ICE and CBP’s operations in Chicago, courts have repeatedly ruled that agents must display their individual IDs to their uniforms in a prominent location. Repeatedly, because the agents are not following the original order to do so. I think it’s well-known at this point that many immigration officers are hiding their faces, and this is in contradiction to the Chicago mayor’s executive order that they must show their faces. They have also been observed using unmarked vehicles without proper license plates.⁷

Since most of the arrests don’t involve warrants, agents are usually targeting people working in public, like gig drivers, street food vendors, and day laborers. As for how they determine who to detain, Greg Bovino made it pretty obvious that part of it is racial profiling in an interview with WBEZ, a local public radio station:

Bovino: You know, there’s many different factors that go into something like that. It would be agent experience, intelligence that indicates there’s illegal alienage in a particular place or location. Then obviously the particular characteristics of an individual, how they look. How do they look compared to, say, you? What’s your name again? [the reporter he’s talking to is white]

Another alarming development here is that agents are pointing their cameras at people’s faces so they can have a facial recognition software determine their immigration status (paywalled):

Ranking member of the House Homeland Security Committee Bennie G. Thompson said in a statement “Mobile Fortify is a dangerous tool in the hands of ICE, and it puts American citizens at risk of detention and even deportation.” He also said “ICE officials have told us that an apparent biometric match by Mobile Fortify is a ‘definitive’ determination of a person’s status and that an ICE officer may ignore evidence of American citizenship—including a birth certificate—if the app says the person is an alien. ICE using a mobile biometrics app in ways its developers at CBP never intended or tested is a frightening, repugnant, and unconstitutional attack on Americans’ rights and freedoms.”

Anyone who’s seen outputs of facial recognition software—Facebook and Apple’s Photos app come to mind—knows that they sometimes make mistakes⁸. Whether the cause is human prejudice or algorithmic bias, the consequences are significant for people who are incorrectly detained. Here is a recent example where ICE detained a permanent resident who is schizophrenic. He was discovered 2 weeks later, miles away from home—it’s hard to know exactly what happened because ICE has not answered his family’s requests for information, while he was detained or after he was reunited with the family.

So far, the immigration agencies have been operating as if there are no consequences to themselves. A lawsuit alleges that detainees at the ICE facility in the suburb of Broadview—a major focus of protests—are being denied confidential calls to lawyers. And the facility has blocked elected officials from inspecting it. (Update 2025-11-04: Multiple former detainees described the inhumane conditions inside the Broadview ICE facility during a court hearing.)

And as I was finishing this post, this article came out. On October 10, a Chicago woman, who is Latina and a US citizen, was driving on the road, minding her own business, when she got hit by an unmarked ICE van. Agents pointed weapons at her, dragged her out without identifying themselves or informing that she was under arrest, then released her after a few hours with no charges.

Tear gas

In October, I stopped being surprised to see new reports of federal agents using tear gas in residential neighborhoods.

Here’s a good look at what tear gas is, and what it’s typically used for. While it’s legal for federal law enforcement officers to use tear gas for crowd control, the big concern with tear gas is that it’s an indiscriminate weapon that affects a whole area, which may include bystanders, especially children and the elderly. Given that, it was clearly inappropriate for federal agents to deploy tear gas in the Logan Square neighborhood on October 3, in a grocery store parking lot, across the street from an elementary school.

The ruling mentioned above from October 9, which required visible identification for agents, also prohibits them from using tear gas on peaceful protesters unless someone poses an immediate threat, and also requires them to give two verbal warnings before using tear gas—so that bystanders can leave the area. These parts of the order are also not being followed, as videos showed the use of tear gas in the neighborhoods of Albany Park and East Side⁹ with no sign of warnings.

Gallingly, Greg Bovino himself was seen on October 22, throwing a tear-gas canister with no apparent verbal warnings in the heavily-Latino neighborhood of Little Village. Eventually, after more high-profile uses of tear gas in Lakeview and Old Irving Park—this one was right before a Halloween parade involving kids in costumes—the same federal judge called Bovino to court on October 26, and reiterated the order. For whatever it’s worth, I believe we have not had agents using tear gas in a neighborhood since that court appearance. (Update 2025-11-10: On the Saturday after I posted this, federal agents used tear gas in Little Village, and used pepper spray on a moving vehicle that had a 1-year-old inside, in Cicero.)

One viral video from the Old Irving Park incident involved a barefoot man in a Chicago Blackhawks pajama pants yelling at the agents. It turns out that he is a former prosecutor:

“I have a lot of close contacts within law enforcement at the state, local and federal level, and almost to a person, none of them support these actions,” Kolp said. “As a lawyer, someone who adamantly believes in the rule of law, watching it in open sight in front of my house just be completely eroded … it’s upsetting.”

Mistreatment of bystanders, journalists, elected officials

While I personally think the government’s response to protesters has been unjust, I also understand that not everyone is on board with protests that interfere with the work of government officials. But what about simply recording what is happening, in a public space? Here’s a case where a woman was filming Border Patrol agents from her car, on the streets of Evanston, just north of Chicago, and the agents threatened her with arrest, claiming that she was impeding them.

This article shows how this is a pattern, where agents threaten to arrest people for following them in their vehicles in order to record them in public. The threat of being charged with a federal crime is a strong one, even if you think you are innocent, and incidents like the shooting of Marimar Martínez, discussed above, are changing how people respond to DHS activity in their neighborhoods:

Previously, two to three cars would mobilize to reported areas where agents were spotted and hop out, blowing their whistles. Now, Enriquez said, they avoid assembling in vehicles while reminding volunteers to not interfere with federal agents.

Along the same lines, DHS has targeted journalists on a few occasions. A CBS reporter had a canister of chemical irritant shot into her car, outside the Broadview ICE facility. This happened just after the Unraveled reporter Steve Held was detained for a few hours, apparently for simply documenting the protests at the facility.

DHS leaders are encouraging this behavior. Chicago Tribune reporter Gregory Pratt posted on X a screenshot of a video showing ICE operating in Little Village. Tricia McLaughlin, DHS’s assistant secretary for public affairs, responded to the post, saying “Why is a Chicago Tribune reporter telegraphing the location of federal law enforcement?“

Finally, many elected officials are working hard to protect their community, and that has often involved documenting the agents, and sometimes confronting them. That has led to incidents where they are detained or threatened. This article I’ve linked above also talks about Chicago Adlerperson¹⁰ Rossana Rodríguez-Sánchez, who was warned for following federal agents in her car, honking and whistling, and State Representative Hoan Huynh, who was surrounded as he sat in his car and had a gun pointed at him.

The most egregious example, especially because it’s clear that the agents were being informed about who they’re talking to, was when Chicago Alderperson Jessie Fuentes was handcuffed at a hospital, for simply asking if they had a warrant on the person they were detaining.

To conclude

This post is not meant to be an exhaustive collection of all the incidents, but it collects what I think are the most unacceptable parts of the federal government’s behavior, and tries to put them in context. I hope I was able to show that, far from the government’s claim that this is about arresting dangerous criminals, its own agents are the ones acting lawlessly, having little regard for people’s rights as defined in the Constitution of the United States, and ignoring judicial orders.

There are many ways to help. As one example, I’ll quote the part of Dan Sinker’s blog post that talks about ICIRR:

Pretty much everything involving witnessing ICE and alerting neighborhoods is running through the Illinois Coalition for Immigrant and Refugee Rights (ICIRR) Family Support Network and Hotline.

• If you spot ICE (in and around Chicago) you can call the ICIRR FSN hotline at 855-435-7693. If you’re in the greater Chicago area, put that number in your phone.

• You can get alerts from the ICIRR’s Eyes on Ice text network by signing up here. (note: this is Chicago-area specific)

• ICIRR also runs Know Your Rights trainings regularly, which are open to anyone.

If this seems like a very long list of things, it is. And I am positive they could use your donation

1. whom I got to know through Chi Hack Night.

2. I second Laurie’s recommendations:

”For daily coverage of federal activity and local response, I recommend Unraveled Press on Bluesky, The Triibe, and Block Club Chicago, though many Chicago news organizations have done great work”

Most of my information has come from Unraveled on Bluesky and Block Club Chicago’s various newsletters.

3. It’s worth noting that overstaying a visa is not a crime, but a civil violation. Yes, by definition, undocumented immigrants have broken some law at some point, but they are not automatically criminals.

4. As the article notes, many Venezuelans arrived in Chicago in 2023 when they crossed the border to seek asylum, and the Texas Governor Greg Abbott bussed them to cities like Chicago.

5. As noted in the South Side Weekly article, an important background to the story is how badly maintained the building was before the raid.

Here’s another article on the raid, from the Economist.

6. A concise quote on how this has been going more recently is in this article:

Resistance works like this: on group chats and on Facebook Live videos, activists share information about when federal agents are spotted. When a spotting is confirmed, dozens of people rush to the scene, blowing whistles, shouting warnings and creating traffic to slow cars. Potential targets are ushered inside, where they cannot be arrested without a judicial warrant. With only 200 CBP officers in Chicago, and a similar number from ICE, getting ahead of them is not that difficult. “There are more of us than them,” says Tatiana Solis, a resident of Pilsen, a largely Hispanic neighbourhood.

7. These are also signs that the operation isn’t about curbing crime at all. When it’s public knowledge that immigration officers are acting in ways that make themselves hard to identify, that’s an invitation for criminals to impersonate them and commit crimes.

8. At my day job, I build machine learning models, and for all but the simplest of problems, you cannot completely eliminate false positives (unless you also eliminate true positives).

And this technical issue is separate from the legality of using facial recognition software in a public space for this purpose.

9. East Side is a neighborhood in the Far Southeast Side of Chicago, right on the Indiana border.

10. There are 50 Alderpersons in the Chicago City Council, each representing one of 50 wards of the city. So they are legislators, but they do a lot of constituent services and often act like “mini mayors” for their wards.