Politics
Debate Over Future of ICE, Response to Immigration Raids Roils Race for Cook County Board President
Left: Cook County Board President Toni Preckwinkle appears on the Oct. 16, 2025, episode of "Chicago Tonight." (WTTW News) Right: Ald. Brendan Reilly (42nd Ward) announces a run for president of the Cook County Board of the Commissioners in a video posted to social media.
The debate over how to respond to President Donald Trump’s aggressive efforts to carry out the largest mass deportation effort in U.S. history is the newest flashpoint in the race for Cook County Board president.
Downtown Ald. Brendan Reilly’s decision to vote, just before Trump began his second term as president, to allow Chicago Police officers to assist federal immigration agents in some cases means he is the wrong choice to lead Cook County, said Toni Preckwinkle, who is running for a fifth term as president of the Board of Commissioners.
“Trump promised mass deportations during the campaign,” Preckwinkle told WTTW News. “Why would you vote to weaken the Welcoming City Ordinance before he took office?”
Reilly, 54, who has represented the city’s 42nd Ward on the Chicago City Council since 2007, was one of 11 alderpeople to vote to consider a measure that would have allowed CPD officers to cooperate with federal immigration agents seeking to deport anyone arrested on suspicion of “gang-related activities,” “drug-related activities,” “prostitution-related activities” or “sexual crimes involving minors” or convicted of similar felony offenses.
Chicago’s Welcoming City Ordinance is designed to ensure that all Chicago residents, regardless of their citizenship or immigration status, can obtain city services, including police protection and medical care, officials said.
Preckwinkle, who is set to celebrate her 79th birthday on Election Day, spotlighted Reilly’s January 2025 vote in an advertisement that linked his vote to the deaths of Renee Good and Alex Pretti, who were shot and killed by federal agents in Minneapolis.
Reilly declined to tell WTTW News whether he regretted that vote, or whether he would vote the same way in the aftermath of what the Trump administration dubbed “Operation Midway Blitz” in Chicago. However, Recent actions by federal agents have made him “look at ICE very differently,” Reilly said.
The purpose of the ordinance he voted for was “to get violent criminals off the streets, including rapists and domestic violence offenders,” Reilly said. “Citizenship, or lack thereof, is not a shield for violent criminals.”
However, CPD and the Cook County Sheriff’s Office have always compiled with judicial orders executed by federal agents. Preckwinkle, Gov. JB Pritzker and Mayor Brandon Johnson have frequently said they are eager to help federal agents deport convicted criminals who are undocumented.
City law prohibits city employees and officials from responding to requests from agencies, including so-called detainers from ICE agents, which seek to have local officials hold undocumented immigrants after completing their sentences until federal agents can take them into custody and start deportation proceedings. Those happen without a court order.
The January 2025 vote was the second time Reilly, one of the most conservative members of the City Council, voted to reconsider the city’s self-proclaimed status as a sanctuary city. In December 2023, he joined 15 other members of the City Council in supporting an effort to ask voters to weigh in on whether Chicago should remain a sanctuary city during the March 2023 election.
Since federal agents shot Good on Jan. 7 and Pretti on Jan. 24, Democratic politicians have been under intense pressure to step up efforts to rein in the actions of ICE and Border Patrol agents.
“Trump’s ICE needs to be abolished, and that agency needs to be returned to the core functions that it had during the Obama administration,” Reilly said, echoing language first used by Pritzker and echoed by moderate members of the Democratic Party, including U.S. Rep. Raja Krishnamoorthi, who is running for the U.S. Senate.
By contrast, Preckwinkle said ICE should be “completely abolished,” since Trump had “weaponized the agency against his enemies” and targeted cities, states and counties led by Democrats.
“We need to start over,” Preckwinkle said.
Many of the ads from Preckwinkle’s campaign highlight decades-old ties between Reilly and Trump, who opened his eponymous Chicago tower in 2009 with the enthusiastic support of Reilly, then in his first term on the City Council.
Preckwinkle blasted Reilly for being largely silent during Operation Midway Blitz, while she said she was proud of using “every tool at my disposal to stand up to Trump.”
Reilly, who posts on X, the social media platform formerly known as Twitter, several times a day, shared a picture from the Oct. 18 “No Kings” anti-Trump rally but does not appear to have posted anything about the presence of hundreds of federal agents in Chicago after they arrived on Sept. 8. Most left the city on Nov. 10, only to return briefly on Dec. 16.
Nor did Reilly mention the immigration raids in his weekly newsletter, even after federal agents paraded through downtown on Sept. 29 and rode military boats along the Chicago River in a show of force, according to an archive of his newsletters.
Several members of the City Council’s Progressive Caucus responded to the aggressive immigration raids by joining community-led efforts to alert residents to the presence of federal agents, with several getting tear-gassed, handcuffed and pushed to the ground in the process.
Preckwinkle signed an executive order prohibiting federal agents from using “county-owned property, resources and personnel for civil immigration enforcement activities” on Oct. 16, after Johnson signed a similar order covering city-owned property.
Reilly said he would not seek to change Cook County’s protections for undocumented immigrants, if elected president of the Cook County Board of Commissioners, nor would he rescind Preckwinkle’s executive order.
“I’m running for Cook County board president because there are major systemic problems with the government itself,” said Reilly, who has repeatedly used his ads to denounce Preckwinkle for her role in the overhaul of the county’s property tax system that led to four months of delays for property tax bills. “This is not my focus. I’m running on affordability issues.”
Preckwinkle called on State’s Attorney Eileen O’Neill Burke on Thursday to pursue “all available charges” against the federal agents who shot and killed Silverio Villegas González on Sept. 12 and the agents that shot Marimar Martinez five times on Oct. 4.
Reilly declined to join Preckwinkle’s call for O’Neill Burke to step up efforts to prosecute federal agents but praised the state’s attorney for working to develop a new “protocol” for handling allegations of wrongdoing or misconduct by federal agents.
Reilly endorsed O’Neill Burke in the 2024 election, while Preckwinkle backed her rival, Clayton Harris III.
“I believe that if anyone commits a violent crime in Chicago or Cook County, they need to be arrested, charged, convicted and incarcerated, period,” Reilly said. “That applies to ICE agents or anyone else.”
No Republican candidate is running for the GOP nomination. The winner of the March 17 Democratic primary will face Michael Murphy, who is running unopposed for the Libertarian Party nomination.
