A new court filing in the Northern District of Illinois alleges that a federal immigration agent pointed a gun at a U.S. citizen and made a threatening remark during a protest in central Chicago’s Little Village neighborhood last week.
By Robert Alexander
The October 26, 2025, filing states that the officer “said, ‘bang, bang,’ and ‘you’re dead liberal.’”
Newsweek contacted the Department of Justice (DOJ), Immigration and Customs Enforcement (ICE), and the Department of Homeland Security (DHS), U.S. Customs and Border Patrol (CBP) Commander Gregory Bovino and Illinois Attorney General Kwame Raoul via email for comment outside of normal office hours on Tuesday.
Why It Matters
The allegations go beyond a single confrontation between a protester and a federal agent. They highlight a growing conflict over how far the federal government can go in enforcing immigration and security operations inside U.S. cities—and how firmly courts can enforce limits on that power.
With a judge’s restraining order already in place, claims that agents ignored it touch on core questions of accountability, the rule of law, and the balance between executive authority and civil liberties on American streets.
What To Know
The document, filed on behalf of journalism organization the Chicago Headline Club and other plaintiffs, claims that agents from DHS violated a temporary restraining order (TRO) limiting their use of force during protests.
The filing identifies the agent as part of a federal team led by Bovino, the head of the U.S. Border Patrol’s Chicago operations.
According to the plaintiffs, a federal officer “pointed a pepper ball gun and then a real gun at declarant Chris Gentry, a combat veteran who was lawfully standing on the side of the road voicing his opposition as agents were driving by in their vehicles.”
The filing states that the officer “said ‘bang, bang,’ and ‘you’re dead liberal.’”
The incident reportedly took place on October 23, during demonstrations in Little Village following federal operations earlier in the week.
Gentry was described as unarmed and not engaged in any unlawful activity.
The same filing also alleges multiple uses of tear gas and pepper munitions by federal agents in violation of Judge Sara L. Ellis’s TRO, which restricted the use of crowd-control devices unless there was “an immediate and serious threat of physical harm.”
The plaintiffs say the conduct documented on video shows “extreme violence against peaceful and innocent American civilians.”
DHS, in a post on its official X account on October 24, defended the agents’ actions, saying they responded to “rioters [who] shot at agents with commercial artillery shell fireworks.”
The post, titled “LAW AND ORDER WILL TRIUMPH IN CHICAGO,” stated that “the mob of rioters grew more hostile and violent, advancing toward agents and began throwing rocks and other objects at agents, including one that struck Chief Greg Bovino in the head.”
It added, “Riot control measures were deployed, including by Chief Bovino, and arrests were made. Agents properly used their training. The use of chemical munitions was conducted in full accordance with CBP policy and was necessary to ensure the safety of both law enforcement and the public.”
DHS also made allegations that Bovino was struck on the head by an object.
Plaintiffs dispute these accounts, asserting in sworn declarations that the demonstrators were “peaceful” and that “no warnings or dispersal orders were given before tear gas was used.”
They further state there is “no evidence that commercial fireworks were fired by anyone at the scene.”
American Immigration Council senior fellow Aaron Reichlin-Melnick commented on the incident online, saying, “DHS has to understand that it’s playing with fire by refusing accountability for officer misconduct like this. People are being completely radicalized by interactions like this.”
The plaintiffs say they have requested any available body-worn camera footage from the incident but have not received a response.
Ellis has not yet ruled on whether the conduct described constitutes a violation of the TRO. A hearing on potential sanctions is expected later this week.
What People Are Saying
Kwame Raoul, Illinois attorney general said September 30, 2025: “Clearly, this deployment of the federal officers into our well-policed central business district is meant to provoke Chicagoans…What the president is hoping to do is foment chaos by inciting out-of-control protests. So I urge Illinoisans: Don’t take the bait. There is no emergency in Chicago.”
Craig B. Futterman, a professor of law at the University of Chicago, on President Donald Trump sending troops into Chicago, said September 8: “His threats to send troops to invade Chicago is a terrifying unconstitutional overreach…This is really threatening the use of the military against its own citizens, against the will of local officials.”
What Happens Next
Ellis will review whether federal agents violated her TPO restricting the use of force during protests. She could hold an evidentiary hearing and, if she finds willful noncompliance, impose sanctions or expand court oversight of federal operations in Chicago.
