Longtime incumbent Preckwinkle faces stiff challenge from Ald. Reilly in Cook County board president primary

Chicago Ald. Brendan Reilly, one of the most conservative members of the City Council, who bills himself as an independent voice, wants a new gig: to run Cook County government.

He’s looking to unseat longtime County Board President Toni Preckwinkle, who doubles as the powerful leader of the Cook County Democratic Party, in the general primary on March 17, Preckwinkle’s 79th birthday.

She oversees one of the biggest counties in the U.S., including the county’s jail, vast court system and large public health system that has a mission to treat patients no matter if they can pay. The county employs more than 20,000 people and has a roughly $10 billion annual budget that must be approved by a 17-member board of separately elected commissioners. Preckwinkle also oversees the Forest Preserves of Cook County.

Reilly, 54, who has represented downtown Chicago for roughly 19 years, is hammering Preckwinkle over a property tax system upgrade that, according to the Chicago Tribune and Injustice Watch, has been plagued by delays. Property tax bills have gone out late, causing school districts across the region to take out loans with interest, as they waited to collect their share of property taxes.

“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 to upgrade the technology behind the property tax system for years, if needed.

Preckwinkle countered she’s one of several separately elected officials who oversee a complicated tax system. Other elected officials, such as the county assessor and treasurer, determine property values and mail 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.”

Preckwinkle is known for running a tight financial ship. She hasn’t raised the county’s portion of property taxes during her 16-year tenure, though a soda tax she supported years ago was repealed after a huge backlash. The county’s pension fund is funded around 66%, more than double some of the city’s pension funds. The county has received four bond rating upgrades since 2021, while Chicago is mired in debt.

Preckwinkle underscores that Reilly and a group of conservative and moderate alders recently muscled through a Chicago budget that includes a host of tax hikes, including a property tax increase for Chicago public libraries. While the budget avoided a new tax on the city’s largest corporations, detested by Chicago’s business community, it “puts the burden entirely on taxpayers while exempting labor from any shared burden,” and included “only a handful of efficiencies and cost savings,” the Civic Federation, a non-partisan government watchdog, wrote in an analysis.

Roughly $5 billion of the city’s $16.6 billion budget this year will go toward pension and debt payments, after decades of mismanagement. That burden contributed to a nearly $1.2 billion gap between revenue and expenses in 2026, as the city has limited avenues to raise money aside from property tax and fee hikes.

Preckwinkle is a former history teacher and longtime Chicago alderperson representing the South Side before she was elected county board president in 2010. She uses her political power and progressive values to shape how the county spends money. She has championed guaranteed income for low to moderate income residents, erased more than $600 million of medical debt, and helped eliminate cash bail in Illinois. She has mentored many into higher office.

Reilly got his start in public service in the 1990s and worked as an aide to now-convicted former Illinois House Speaker Michael Madigan. He left for the private sector and worked as an AT&T executive before defeating long-serving City Council incumbent, Burt Natarus, in 2007.

Reilly hasn’t faced an opponent since. In 2020, he broke with the Democratic Party to endorse Republican Patrick O’Brien over Kim Foxx, Preckwinkle’s former chief of staff, for Cook County state’s attorney.

Preckwinkle runs again because of Trump

Preckwinkle said she was inspired to run for a fifth, four-year term to guard against Republican President Donald Trump. His One Big Beautiful Bill calls for sweeping cuts to public programs that support thousands of county residents, and could put a big dent in the overall county budget.

As immigration agents detained people off the streets and fired pepper balls and tear gas at protesters throughout Chicago and the suburbs, she issued an executive order to create “ICE-free zones” in Cook County.

“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 points to his support for a measure aimed at creating carveouts in Chicago’s sanctuary law that prohibit police from helping with civil immigration enforcement. Reilly was one of 11 Council members who pushed for a vote on the now-stalled measure, after a chorus of advocacy organizations warned it would open the door to constitutional rights violations and legal challenges.

In a statement, Reilly said he supports abolishing U.S. Immigration and Customs Enforcement and returning the agency to its “core functions during the Obama administration.” He said he would defend the county’s restrictions on using local resources for certain federal immigration enforcement. But he supports carveouts for people arrested or convicted for felonies such as sex crimes involving children or gang-related violence.

One of the biggest challenges the county faces is bracing for an estimated almost $300 million in losses per year, largely due to people losing their health insurance. Low-income residents who have public Medicaid health insurance will have new work requirements next year and more frequent checks to make sure they qualify, while others might drop insurance they bought on the government exchanges because subsidies are gone.

People might still show up for medical care at Cook County Health’s two hospitals and several clinics, but might not be able to afford to pay what could be big bills. That means less money flowing to the county. The majority of the county’s patients have Medicaid or no insurance, records show. Dr. Erik Mikaitis, CEO of CCH, said the amount of uninsured patients is already swelling.

Reilly said the county should have planned for Medicaid losses earlier.

“You don’t wait for federal cuts to happen,” Reilly said. “You build a firewall before they hit.”

County leaders say they have been preparing. The health system started tightening its belt last year, with 10% cuts across all departments that will continue through 2026. They froze about 200 vacant positions. The county has set aside around $320 million in reserves, partly in case federal grants for everything from transportation to public health get cut, and nearly $70 million for potential Medicaid losses, a county spokesman said.

Reilly suggests pre-ranking medical services to keep or cut, prioritizing the ER and trauma care. He declined to say what he would cut, deferring to the health system.

Mikaitis said there are contingency plans — not cutting services but potentially consolidating them, such as offering a service in three clinics instead of five.

Reilly suggests a Cook County ID

In a statement, Reilly said he wants to make sure “Cook County services are for Cook County residents,” and that the county isn’t absorbing costs from other counties. He points to WBEZ reporting that underscores the impact on county finances for providing the most charity care, or discounted care, of any hospital in Illinois — around $217 million at the county’s John H. Stroger Jr. Hospital in 2024, a WBEZ analysis of the most recent state records shows. In some cases, private hospitals stabilize patients, then refer them to the county for follow-up care.

“Verified residency and referral data would allow the county and the Attorney General to audit community benefit reports, enforce state discount laws, and hold private systems accountable when costs are shifted onto the public safety net,” Reilly said.

A health system spokeswoman said only about 4% of patients live outside the county. The county’s financial assistance program, CareLink, is only for county residents, and an Illinois law caps how much any hospital can collect from uninsured patients who live in the state. Patients who live outside of Illinois and pay out of pocket could qualify for a discount.

Reilly said a countywide ID, which county commissioners have floated before, would help people prove residency for county services, such as medical care. The idea is not to restrict care or duplicate existing ID programs, like Chicago’s CityKey, Reilly said. The county ID would be for suburban residents, he suggests.

Whoever wins the Democratic primary would likely win in the November general election. There is no Republican candidate for county board president. Michael Murphy is running as a Libertarian. Preckwinkle last won with about 69% of the vote in 2022 against Bob Fioretti.

Should she win, Preckwinkle said it would be her last term as county board president. She said she also plans to run for just one more, two-year term this spring to lead the Democratic Party.

Kristen Schorsch and Mariah Woelfel cover government for WBEZ.