By Chris Tye, Sara Tenenbaum
Click here for updates on this story
CHICAGO, Illinois (WBBM) — Federal officials who want immigration agents to detain and deport Cook County Jail inmates have threatened Sheriff Tom Dart with prosecution if he doesn’t give them access.
Federal agents looking to detain and deport Cook County Jail inmates have threatened Sheriff Tom Dart with prosecution if he doesn’t give them access.
Letters hand-delivered to Dart’s office in July send a clear message that U.S. Immigration and Customs Enforcement agents want access to people being detained in the jail.
Dart denied the request and so far has not been prosecuted, but the threats are the clearest signal yet that the U.S. Department of Homeland Security wants to take people into custody in a less public way than unfolded in 2025 during Operation Midway Blitz.
During Operation Midway Blitz thousands of people were arrested, the National Guard waited in the wings and body-worn cameras became a requirement for agents, an unblinking eye that captured some but not all of the immigration crackdown — including the missteps and misbehavior of agents.
Since then, DHS got a new boss who has signaled he wants deportations to continue at the same pace, but in a less visible way.
“We are going to take a different approach that can be more effective and less public facing,” Markwayne Mullins said in June.
“I’m being told every day things are happening, people are being deported, swept up, in a much more clever way,” said retired judge Ruben Castillo, the head of the Illinois Accountability Commission. “It’s hard to nail that down. There’s not easy ways to videotape.”
After Operation Midway Blitz wound down in November 2025, many expected a return to forceful immigration crackdowns in Chicago in the spring, but the spring surge never happened. Instead, this quieter, less public campaign focused on places like airports has emerged.
Sunday, a Chicago-based DJ from Colombia who was set to tour with Colombian pop star Karol G and his partner were detained by ICE agents at Midway International Airport as they were on their way out of the city.
Another way to keep immigration enforcement out of the public eye is to not take people off the streets, but instead from jails. The New York Times first reported Wednesday that agents from ICE and DHS have asked for, and been denied, access to inmates in the Cook County Jail.
Four letters have arrived at Dart’s office in over the last month, telling him to hand over four inmates at the jail. Three of them had already been released; the fourth, Dart refused.
In response, the feds warned Dart that he was witness tampering and could face federal felony charges. Similar letters were also sent to Hennepin County Sheriff Dawanna Witt, whose jurisdiction includes Minneapolis which is also a sanctuary city.
“I think Sheriff Dart is being put in a very difficult situation because he has to comply with Illinois law,” Castillo said.
In a statement, Dart’s spokesperson said, “The subpoena demanded the person to attend an interview at the federal agency’s office…Per state law and the applicable court orders that mandate the Sheriff’s Office to keep a person in custody, the Sheriff’s Office cannot release an individual in custody to any law enforcement agency or federal agents for an interview.”
“It’s not going to happen,” said CBS News Chicago Legal Analyst Irv Miller. “Legally, it cannot happen.”
Miller said the legal threat has no teeth, and would be immediately tossed in court.
“To threaten a sheriff, an elected sheriff of Cook County or any other county, is not the proper way to go,” he said.
profile ways to go about rounding up undocumented individuals out of camera range.
Castillo said the new tactic creates new anxiety even for those who have done nothing wrong.
“In non-visible, non-video recorded manner, they want to detain people, and they’re going to cut corners with the law,” he said.
Federal officials have told Dart that if he can’t hand inmates over now, then they request he alert them when they’re released. Dart’s office said the sheriff’s office is not allowed to turn individuals over upon release for an interview with federal agents or any other law enforcement agency.
In an emailed statement, DHS told the New York Times the letters “were an effort to compel ‘sanctuary politicians’ to hand over dangerous criminals so they can be deported.”
The New York Times also reported that a spokesperson for the National Sheriffs’ Association told them Monday that their group did not know of any other sheriff that had been threatened with criminal charges over allowing ICE access to inmates for deportation.
In a statement late Thursday night, a Department of Homeland Security spokesperson said “This isn’t news.”
“In President Trump’s first term subpoenas were commonly used to compel local and state law enforcement that REFUSED to cooperate with federal immigration authorities and detainers,” the spokesperson said. “In the president’s second term, we’re continuing these efforts as sanctuary politicians refuse to hand over the worst of the worst criminal illegal aliens. Non-cooperative jurisdictions have a choice: stop harboring criminal illegal aliens and releasing them into their communities, or work with ICE to make America safe again. Either way, ICE will not be slowing down on enforcing federal law.”
Chicago has been a sanctuary city for decades, and targeted by Trump before Chicago has had sanctuary city policies since 1985, originally established by Mayor Harold Washington in 1985 through executive order. The city officially passed the “Welcoming City Ordinance” in 2006, and it’s been updated multiple times since, including in 2012 when Rahm Emanuel was mayor and in 2021 when Lori Lightfoot was on the fifth floor of City Hall.
It’s backed up by the Illinois TRUST Act, which was signed into law by Republican Governor Bruce Rauner in 2017. Both the ordinance and the act largely prohibit law enforcement from cooperating with federal immigration agents, and from stopping, arresting, searching, detaining or continuing to detain a person solely due to immigration status.
In January 2025, the Chicago City Council blocked a bid by some of their more conservative alders to water down the ordinance amid threats from President Trump to make the city “ground zero” for his mass deportation plans as he readied himself to begin his second presidential term.
Last summer the city joined a coalition of local governments in suing Mr. Trump and his administration over withholding funding for “sanctuary jurisdictions” that would not cooperate with immigration enforcement.
And since taking over as Homeland Security secretary, Mullins has threatened several times to remove all U.S. Customs and Border Patrol agents from airports in sanctuary cities, including Chicago.
Please note: This story was provided to CNN Wire by an affiliate and does not contain original CNN reporting. This content carries a strict local market embargo. If you share the same market as the contributor of this article, you may not use it on any platform.
