Chicago-area cops helped HSI spy on anti-ICE activists in Minnesota

Despite Illinois sanctuary laws, local police in and around Chicago helped ICE investigative agents track down activists who engaged in activities protected by the First Amendment.

According to newly released documents reviewed by WIRED, Chicago-area law enforcement officers participated in an undercover ICE investigation into Minneapolis mutual aid networks last spring as part of a federal conspiracy investigation into 15 Twin Cities activists facing federal felony charges for resisting Operation Metro Surge.

An April report by ICE's investigative division, Homeland Security Investigations, titled "Antifa Roadshow," details in-person and electronic surveillance by a joint task force at the April 2 speech. The task force consisted of 14 law enforcement officers - six local police and eight Chicago HSI agents. The conversation included self-described anarchists in Minnesota who spoke about their experiences organizing during the three-month immigration wave that left two U.S. citizens dead.

The document, released by the defense team of 15 Minnesota activists as part of the ongoing federal case against them, reveals close cooperation between local police, sheriffs and HSI agents in a prosecution that critics say crosses the line into political repression. HSI Chicago's task force, which included officers from Chicago, Aurora, Downers Grove, Cook County and Kane County, used two undercover agents, unspecified electronic surveillance, voice recordings, license plate reader data and surveillance cameras from Chicago's extensive CCTV network to identify connections to anti-participant April 1 protests in Illinois and other states.

Records provided by the Kane County Sheriff's Office show the unit in question is the Chicago Area Homeland Security Investigations Task Force. Local policemen who join this unit are accepted for two years full-time or part-time with the signature of their superiors.

Since Operation Midway Blitz in Illinois last fall, residents of Chicago and surrounding communities have pressed elected officials for answers about cooperation between local law enforcement and ICE. While Illinois state law prohibits local law enforcement from participating in immigration enforcement operations, criminal investigations by HSI appear to fall outside those restrictions as they relate to other ICE law enforcement duties.

Chicago police have significant clearance requirements to monitor and intervene in protests or public gatherings, according to a 2017 executive order. It's unclear how the regulations would apply to Chicago Police Department officers who participate in joint task forces with federal agencies.

In response to questions from WIRED, CPD claims that no First Amendment notification was made to CPD's chain of command or the department's attorney general for the April 2 investigation, and says that its work with HSI is authorized under Illinois law because it relates to criminal enforcement, not immigration. A source familiar with the matter said CPD believes an early April surveillance operation serving as part of a federal theft investigation is the only financial element listed in the report of a GoFundMe account to support the Crimethinc speaking tour. There is no mention of funds requested or received at the April 2 event.

The Chicago mayor's office did not comment ahead of publication. In response to questions from WIRED, ICE would not confirm or deny details of past or current investigations and said individual agents are not authorized to speak to the media.

HSI is also emerging as the lead agency in Trump's war on domestic dissidents and opposition politicians: Its agents, not the FBI, conducted the Minnesota 15 investigation and earlier this month served a search warrant on Minnesota Congressman Ilhan Omar.

The targeted April 2 event took place at Co-Prosperity, a leftist gallery in Chicago's Southside neighborhood in Bridgeport. Several speakers from the Twin Cities area attended the event to share information about resisting increased federal immigration. It was part of a national tour last spring organized by the longtime anarchist group Crimethinc, whose meetings have been repeatedly infiltrated by federal informants over the decades and helped convict Eric McDavid, as well as Matthew DePalma, a protester at the 2008 Republican National Convention.

According to HSI's four-page report, a plainclothes cop from suburban Aurora was flagged down at the Co-Prosperity event by Officer Mike Zhou of the affluent village of Downers Grove. HSI undercover agent #9147 arrived five minutes later, when undercover cops from Aurora confirmed that no security checks had been done at the door.

The HSI undercover agent transmitted a live recording of the event to the rest of the surveillance team for an hour until the transmission was lost. The recordings of the incident were uploaded and shared with Kenneth Popowitz, a financial crimes investigative supervisor working on a temporary assignment in Minneapolis.

Defendant Calum Robint's statements from an April 2 speech in Bridgeport about building rapid response networks are included in a federal conspiracy indictment filed against Minnesota 15 that implicates Chicagoland law enforcement involved in the controversial prosecution.

The Aurora Police Department, the Downer's Grove Police Department and the Kane County Sheriff's Office did not respond to requests for comment.

HSI Chicago's surveillance team recorded 219 vehicles parked in the vicinity of Co-Prosperity. Several subjects were already identified by ICE as being under investigation, including some of the speakers on the tour. Kane County Sheriff's Deputy Ryan Wasson saw a hooded and masked man outside the dealership removing an object from his trunk. Wasson, who had the license plate, arrested the man on Oct. 4 during an Operation Midway Blitz that was dismissed by Assistant U.S. Attorney Christopher Veach.

Outside the location, Agents Joel Sullivan and Michael Finnerty observed an unidentified subject previously being investigated for running an anti-ICE chat and signal group called the ICE Cream Patrol, and noted that an orange Hyundai was registered near two March 2026 demonstrations outside the ICE detention center in Broadview, Illinois. The surveillance continued for approximately two hours until 8:30 p.m. local time on April 2.

Nick Nunez, a veteran Chicago police detective who briefed the joint task force, filed a request to obtain surveillance footage from the CPD camera outside the venue. It took a week to complete the request and it is unclear if he received the footage. According to the agency's report, all information obtained during the April investigation in Chicago with HSI St. Paul/Minnesota shared.

Ed Yohnka, a spokesman for the American Civil Liberties Union of Illinois, called the surveillance of the Bridgeport rally "extremely troubling," adding that local law enforcement should complete its role in the incident and participate in joint task forces with federal auditing agencies.

"No one should be subject to law enforcement surveillance and influence simply because they engage in constitutionally protected activities, including the ability to assemble and express dissatisfaction with public policy," Yohnka said. It's also a moment for local law enforcement to reexamine their involvement in Trump administration task forces, especially any group focused on fighting "terrorism."

The April 2 meeting in Bridgeport is not the only out-of-state gathering spied on by HSI during the Minnesota 15 investigation. Reports obtained by defense attorneys through discovery show that events on the same Crimthink tour in Ann Arbor, Michigan, and Seattle, Washington, were personally monitored by local HSI agents who reported the content of the speech to their colleagues in Minneapolis.