On November 5, 2025, a federal courtroom in Chicago became the latest battleground in the country’s intensifying debate over immigration enforcement, civil liberties, and the use of force by federal agents. U.S. District Judge Sara Ellis, who had already imposed strict limits on federal immigration officers’ actions in the city, is now weighing whether to extend those restrictions after a series of violent confrontations between agents and protesters, many of which have been captured on video and circulated widely.
Since early September, federal agents from Immigration and Customs Enforcement (ICE) and U.S. Customs and Border Protection (CBP) have carried out “Operation Midway Blitz,” a sweeping enforcement campaign in the Chicago area. According to reporting by NextShark and court documents, these officers have repeatedly deployed chemical irritants, pepper balls, and tear gas against demonstrators—tactics that experts say breach professional norms and push the boundaries of what’s legally acceptable in urban settings.
The crackdown has not gone unnoticed by local residents. Community groups have mobilized, using Facebook networks with tens of thousands of members to track agent movements and alert neighbors. Some have taken to following enforcement vehicles, honking car horns or blowing bicycle whistles to warn others. The result has been a tense, sometimes chaotic standoff between federal officers and a city determined to resist what many see as an overreach of federal power.
The legal fight began in earnest on October 9, when Judge Ellis issued a temporary restraining order barring federal agents from using riot control weapons—such as tear gas and pepper balls—against journalists, protesters, and religious practitioners without first issuing warnings, unless there is an immediate and serious threat of physical harm. The order also prohibited agents from dispersing, arresting, or threatening to arrest anyone they should reasonably know is a journalist. On October 16, Ellis expanded the order to require federal agents equipped with body-worn cameras to keep them on during law enforcement activities in the Chicago region. These measures were set to expire on November 6, but the question of whether to extend them has gained urgency as new evidence of alleged violations has emerged.
In recent weeks, attorneys representing journalists, clergy, and protesters have submitted video footage and eyewitness accounts to the court, alleging that Department of Homeland Security (DHS) agents have repeatedly ignored the judge’s order. One particularly disturbing incident unfolded in Evanston, Illinois, on October 31. Video from the scene shows a federal agent pressing a man’s head to the ground for nearly two minutes as the man repeatedly cries out, “I can’t breathe.” An eyewitness told the court, “I saw a federal agent bash his head on the street at least two times.” The same witness said the agent then “struck the young man in his head with his hand or fist at least two times.”
David Brooks, who filmed the Evanston confrontation, described a frightening escalation: “A Border Patrol agent pointed a pistol at me. ‘Step back or I’m going to shoot you,’ the agent allegedly told Brooks. ‘I took a step back and said you’re gonna what,’ Brooks wrote. ‘He then pulled out his pistol from his holster and pointed it directly at me. I was startled and stepped back again. He holstered the gun.’”
Federal officials, however, tell a very different story. DHS Assistant Secretary Tricia McLaughlin said agents were responding to a dangerous situation after being “aggressively tailgated” by a vehicle that crashed into them. “A hostile crowd then surrounded agents and their vehicle and began verbally abusing them and spitting on them. One physically assaulted a Border Patrol agent and kicked an agent. As he was being arrested, he grabbed the agents’ genitals and squeezed them. As you know this is an extremely painful experience for most human beings and justifies certain responses, the agent delivered several defensive strikes to the agitator to free his genitals from the agitator’s vice,” McLaughlin said.
The government’s filings in court echo this stance, asserting that “although some protests remained peaceful, others turned violent. Rioters have attacked law enforcement personnel with fireworks, rocks, and other objects. Rioters also breached the perimeter of federal buildings, blocked all traffic into the only immigration facility in the region, damaged federal vehicles, and injured officers. At some violent protests, officers responded by issuing dispersal orders and using nonlethal crowd-control devices.”
Yet critics argue that the government’s response has gone far beyond what’s necessary to ensure officer safety. Plaintiffs in the ongoing lawsuit allege “extreme violence against peaceful and innocent American civilians.” According to court documents and NextShark, at least 170 U.S. citizens—including combat veterans—have been wrongfully detained, sometimes for days. There are reports of officers tackling people who were simply recording raids, and of agents zip-tying children before separating them from their parents. The chilling effect on the community has been palpable: Halloween festivities were notably subdued after Illinois Governor JB Pritzker’s call to suspend the operation was dismissed as “shameful” by DHS Secretary Kristi Noem.
Since “Operation Midway Blitz” began on September 6, 2025, federal agents have made over 2,800 apprehensions in the Chicago area alone. Nationwide, ICE is holding nearly 60,000 detainees, most of whom do not have criminal records, according to government data cited by NextShark. The scale and intensity of the operation have alarmed civil rights advocates and lawmakers alike. Illinois Senator Tammy Duckworth has called for independent investigations by the Department of Justice and DHS into what she describes as the “outrageous use of force.”
Experts have also weighed in, questioning both the appropriateness and the effectiveness of the tactics used. Former ICE Director John Sandweg told the Washington Post that methods “appropriate” for remote desert operations against drug cartels are not suitable “when you bring them up to civil immigration enforcement in a city like Chicago,” noting that agents have limited training for urban demonstrations.
The implications extend far beyond Chicago. Asian American communities, in particular, face heightened risk, with advocates warning that the aggressive enforcement tactics could soon be exported to other cities and urban centers. The deployment of military-grade crowd control devices in diverse neighborhoods, where language barriers and fear of authorities already discourage residents from asserting their rights, threatens to normalize aggressive enforcement and erode constitutional protections for all.
As Judge Ellis weighs whether to extend her restraining order, the legal and moral questions at the heart of the Chicago crackdown remain unresolved. The outcome could set a precedent for how federal agents operate in American cities—and for the rights of those who dare to protest.
The city’s residents, legal advocates, and officials now wait for the judge’s decision, knowing that whatever she decides will reverberate far beyond Chicago’s streets.
