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How Trump’s Chicago Immigration Crackdown Escalated, in 10 Videos

October 12, 2025
in News
How Trump’s Chicago Immigration Crackdown Escalated, in 10 Videos
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Crowds of bystanders heckled and pointed cellphone cameras at federal agents during arrests. Immigration officers deployed tear gas and fired pepper balls to disperse protesters. Schools emailed parents in the middle of the day with warnings: Immigration agents might be nearby.

These scenes from the Chicago area in recent days looked far different from what residents were seeing along city streets about a month ago, when the Trump administration announced the start of a crackdown on illegal immigration in Chicago and its suburbs.

What began with a slow uptick in arrests has escalated rapidly. One unauthorized immigrant was fatally shot. American citizens have been detained along with undocumented immigrants. Border Patrol agents have walked in groups through downtown Chicago. Residents have given chase to federal agents’ vehicles. And chemical agents have been used on protesters, journalists and clergy members.

By this week, tensions were high, and many Chicagoans said they sensed a city on edge.

The New York Times reviewed more than 100 videos taken in the Chicago area over the past month, chronicling the actions of federal agents and the response by the public. Videos captured protests, raids, arrests on city streets and residents’ confrontational responses. Together, the videos show how tensions have risen, unfolding in charged and adversarial scenes in locations scattered around the city.

Federal authorities originally told local officials that they expected the operation to last 45 days. There now appears to be no end in sight.

Sept. 5-11

A Slow Ramp Up

From the beginning, residents in heavily Latino neighborhoods in the city were wary of the promised escalation by immigration authorities. But in a city of 2.7 million spread out across more than 200 square miles, other residents seemed unconcerned or unaware, with few early signs of a crackdown visible along their streets.

Some residents began sharing information on social media about possible sightings of immigration authorities in the city and in far-flung suburbs, warning one another to stay alert. Other residents applauded the actions of federal agents, saying that they supported efforts to more strictly enforce immigration law.

Thousands marched downtown in an energetic protest, chanting and beating drums while denouncing Immigration and Customs Enforcement and shouting support for other causes, including the plight of Gazans in the Middle East.

Then President Trump delivered a startling threat online, writing on Truth Social: “Chicago about to find out why it’s called the Department of WAR.”

Immigration arrests by federal agents were nothing new in Chicago. And small, regularly scheduled protests and prayer groups had been held outside an ICE processing facility in Broadview, a suburb about 30 minutes from downtown, for years. But this felt different. Federal authorities boarded up windows and doors of the ICE facility, and more and more protesters began gathering outside on some evenings.

Celebrations for Mexican Independence Day mostly carried on. But tensions flared. On the Southwest Side, a street vendor who was known for the flowers he sold outside a car dealership was arrested by federal agents. He was later deported to Mexico.

A video of his arrest spread on social media, angering community members. For days, neighbors left flowers and candles on the sidewalk where he had worked.

On Sept. 8, the Department of Homeland Security officially announced the start of Operation Midway Blitz, targeting “the worst of the worst criminal illegal aliens in Chicago.” Sightings of immigration arrests began to multiply.

Sept. 12-28

A Shooting Alarms the City

On the morning of Sept. 12, two immigration officers pulled over a man driving a silver Subaru on a busy street in a Chicago suburb shortly after he had dropped off his children at an elementary school and day care. When the driver attempted to pull away, an agent shot him in the neck. Officials said that the man, Silverio Villegas-Gonzalez, a Mexican national who federal officials said was not authorized to live in the United States, had attempted to hit the officers with his car. He did not survive.

At Broadview, confrontations between federal agents and demonstrators began to intensify. Immigration officers stood on the roof, firing tear gas and bean bag rounds at protesters who were trying to block federal vehicles from exiting and entering the facility.

On Sept. 19, video captured federal agents firing pepper balls at the Rev. David Black, a pastor of the First Presbyterian Church of Chicago, from the facility’s roof while he held his hands up in a gesture of prayer as he stood to the side of an entrance gate for vehicles. Reverend Black fell to his knees and clutched his head.

Trump administration officials have defended the actions of immigration authorities on social media, saying that residents were interfering with lawful arrests.

Tricia McLaughlin, the assistant secretary for public affairs for D.H.S., shared the video on X, referring to the group as “agitators” who were blocking an ICE vehicle from leaving the federal facility.

More than a week after the crackdown began, Kristi Noem, the homeland security secretary, arrived in the Chicago area, sharing footage from a nighttime raid in Elgin, Ill., about an hour outside the city, in which five people were arrested.

She was soon followed by Gregory Bovino, a chief of the Border Patrol in Southern California. Border patrol agents, in full uniform and some in face masks, rode in boats along the Chicago River, where tourists regularly gather. Groups of the agents marched through the middle of downtown, startling shoppers who fill the business district. Some were alarmed and filmed the agents on cell phones.

The Trump administration released their own slickly produced video with footage of agents with weapons patrolling along the river.

At Broadview, tensions kept growing. Authorities built an eight-foot fence around the building as protesters and agents continued to clash. Along the way, more cellphone videos of immigration arrests began to circulate — roofers detained in Naperville, a family in Millennium Park.

In one moment, a man was seen taunting Border Patrol agents in downtown Chicago before narrowly escaping on his bike as the agents stumbled after him. Images of the fleeing cyclist — and memes cheering him along — filled social media.

Sept. 30-Oct. 7

A Raid Ignites Anger

Then came a nighttime raid by Border Patrol agents on a five-story apartment building on the city’s South Side. Neighbors were startled by the sound of Blackhawk helicopters and federal vehicles outside. Residents of the building said they saw dozens of people zip-tied and detained in what local and state officials characterized as a publicity stunt intended to intimidate residents.

A video taken by a resident across the street from the South Side apartment complex showed immigration authorities conducting a military-style operation on a residential street, with agents riding on armored vehicles and a helicopter overhead.

In the last two weeks, many Chicagoans began to aggressively push back. Some residents honked their horns, yelled and gave chase when they saw immigration authorities’ vehicles. Onlookers crowded around agents with their phones out, recording. In one video, filmed on the West Side of Chicago, bystanders could be heard taunting federal agents with chants like “Get real jobs!” Some people in the group chased the agents’ truck down the road.

Last weekend, tensions escalated further.

Outside the ICE facility in Broadview, federal agents threw smoke bombs at a large group of protesters, tackling and slamming others to the ground. Protesters heckled agents about their roles in carrying out President Trump’s deportation efforts, calling out questions to the agents like “What are you going to tell your children?”

In footage shared with The Times, federal agents shouted at a group of protesters to move. “You’re getting ready to get it,” Mr. Bovino told the crowd, threatening them with arrest, while members were yelling at the agents. Mr. Bovino grabbed a man and tackled him to the ground with the help of another agent.

And on Saturday morning, Border Patrol agents said they were chased by two Chicago residents in cars. The residents ran red lights and stop signs as they pursued them, the agents said. The altercation ended with one of the motorists being shot several times by federal agents. Neighbors gathered at the scene in protest, and federal agents used tear gas to disperse the growing crowd.

Chicago police officers, given no warning to wear protective masks, were among those exposed to the tear gas.

Other scenes captured that day showed federal agents tackling people. In one video, an agent could be seen repeatedly telling a man standing close to him to step back. The agent then grabbed the man by the neck. Other agents joined, as they took the man to the ground.

Outside Chicago, federal agents were filmed making arrests in suburbs, including Waukegan, Berwyn and Cicero.

On Wednesday night, around 1,000 people gathered in downtown Chicago to protest. About 200 troops from the Texas National Guard had arrived earlier that day, further inflaming a city already on edge.

Jamie Leventhal contributed additional video editing.

Julie Bosman is the Chicago bureau chief for The Times, writing and reporting stories from around the Midwest.

Allison McCann is a reporter and graphics editor at The Times who covers immigration.

The post How Trump’s Chicago Immigration Crackdown Escalated, in 10 Videos appeared first on New York Times.

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