Reilly Challenges Preckwinkle for Cook County Board President

The 54-year-old alderman who has represented downtown Chicago for 19 years is betting voters are ready for change after Preckwinkle’s 16-year tenure running the county’s $10 billion operation. The election falls on Preckwinkle’s 79th birthday.

Reilly is centering his campaign on the county’s troubled property tax system upgrade, which has caused delays in tax bills going out and forced school districts across the region to take out loans while waiting for their share of property tax revenue.

“While my opponent has had a great career in public service, she’s stayed a bit too long,” Reilly said. “Cook County government is broken in a number of areas that are making it a lot less affordable to be able to live here.”

Reilly said he would terminate the county’s contract with Tyler Technologies, which has been working for years to upgrade the technology behind the property tax system.

Preckwinkle defended her record, pointing out that multiple separately elected officials oversee the complicated tax system. County assessors determine property values while the treasurer mails tax bills.

“My view has been to try to get people to work together to solve the problems,” Preckwinkle said. “You can’t do that if you point fingers and throw people under the bus.”

The county board president oversees one of the largest counties in the country, including Cook County Jail, the court system and a public health system that treats patients regardless of their ability to pay. The county employs more than 20,000 people and operates the Forest Preserves.

Preckwinkle has maintained tight fiscal control during her tenure, avoiding property tax increases on the county’s portion while building up pension funding to 66 percent - more than double some city pension funds. The county has received four bond rating upgrades since 2021, even as Chicago struggles with debt.

She fired back at Reilly’s criticism by highlighting his role in the recent Chicago budget battles. Reilly and other conservative and moderate aldermen pushed through a city budget with multiple tax hikes, including a property tax increase for Chicago public libraries. The Civic Federation criticized the budget for putting “the burden entirely on taxpayers while exempting labor from any shared burden.”

The two candidates present starkly different political profiles. Preckwinkle, a former South Side alderman and history teacher, has used her progressive values to shape county spending. She has championed guaranteed income programs, erased more than $600 million in medical debt, and helped eliminate cash bail in Illinois.

Reilly started in public service as an aide to now-convicted former Illinois House Speaker Michael Madigan before moving to the private sector as an AT&T executive. He defeated longtime incumbent Burt Natarus in 2007 and hasn’t faced an opponent since. In 2020, he broke with the Democratic Party to endorse Republican Patrick O’Brien over Kim Foxx for Cook County state’s attorney.

Preckwinkle said Trump’s presidency motivated her to seek a fifth term. She issued an executive order creating “ICE-free zones” in Cook County as federal immigration agents detained people throughout Chicago and the suburbs.

“Trump’s declared war on us,” Preckwinkle said. “We need somebody who’s going to stand up to him and stand for our residents and the rule of law. He’s not that man,” she said of Reilly.

She criticized Reilly’s support for creating carveouts in Chicago’s sanctuary law that would allow police cooperation with immigration enforcement in certain cases.

Reilly said he supports abolishing Immigration and Customs Enforcement and would defend county restrictions on using local resources for federal immigration enforcement, but backs exceptions for people convicted of serious felonies.

Both candidates face the challenge of potential federal budget cuts that could cost the county nearly $300 million annually. Low-income residents may lose Medicaid coverage due to new work requirements, while others might drop insurance as subsidies disappear.

Reilly criticized the county for not preparing earlier for potential losses. County officials say they have been planning, setting aside $320 million in reserves and nearly $70 million specifically for Medicaid losses.

Reilly also proposed creating a Cook County ID to help residents prove residency for county services, particularly medical care at county facilities that provided $217 million in charity care in 2024.

The Democratic primary winner will likely take the general election, as no Republican candidate filed for county board president. Preckwinkle won her last election in 2022 with 69 percent of the vote and said this would be her final term if elected.