Cook County Board president candidates tussle over costly tech upgrade
Jan 26, 2026
If elected Cook County Board president, downtown Ald. Brendan Reilly said Monday he would launch a “full review” of Tyler Technologies — the Texas firm that has been working for more than a decade on upgrading the county’s property tax systems — “to put a stop to the total mismanagement
of its tax system under the leadership of Toni Preckwinkle.”
Reilly and Preckwinkle are set to face off in the March Democratic primary to lead the Cook County Board, the county’s $10 billion budget, and its health system and Forest Preserve District. Reilly has made one of his core criticisms of Preckwinkle’s four terms as board president the long-standing, ongoing problems with upgrading the county’s property tax system, which have led to a significant delays and lots of finger-pointing among elected officials seeking to avoid blame.
In an endorsement session with the Chicago Tribune Editorial Board, Preckwinkle acknowledged the latest problems with the upgrade that delayed distributions of tax money “have real consequences for schools and other taxing bodies,” but noted that she tried to minimize the damage by offering short-term interest-free bridge loans.
“I don’t control assessment or distribution,” she repeated twice, also pointing out property tax bills were late for decades before she took office. Those functions are run by the separately elected county assessor, clerk and treasurer. Preckwinkle and the County Board authorized the Tyler contract, and her Bureau of Technology has refereed its implementation.
School districts estimate the delays cost $122 million between the interest and issuance costs of borrowing, cashing out investments or forgoing investment income that would have otherwise built up if revenue had come out on time. Many districts didn’t qualify for Preckwinkle’s bridge loan program because their credit ratings or reserves were too strong.
Tyler won two contracts to update the county’s court and property tax records systems, costing up to $38 million. As delays have mounted, so have ancillary project management costs and the price of keeping the county’s mainframe computers running.
Cook County Board President Toni Preckwinkle speaks during a news conference at the Bronzeville Health Center on Jan. 5, 2026. (Eileen T. Meslar/Chicago Tribune)
The latest delay affecting property tax distributions was not Tyler’s fault — county stakeholders belatedly realized they had been testing on an incorrect file — but school districts have been upset about a lack of communication from county leaders to plan for those delays.
“We depend upon cooperation and collaboration from agency stakeholders, as well as timely and consistent information and guidance from those partners,” Tyler Chief Administrative Officer Abigail Diaz wrote in a recent letter to the editor published Sunday in the Tribune.
Reilly said in Monday’s meeting with the editorial board that “Cook County has a responsibility to help” with the cost of delayed property tax bills to other taxing bodies.
Preckwinkle’s team is meeting with some school district leaders later this week to air their concerns “and to assure them” they can count on distributions coming out on time during the next tax cycle in April. A Tyler spokesperson said 85% of tax revenues from the bills due in December have been distributed.
Reilly said in a news release just before the editorial board meeting that he “would not hesitate to terminate this contract and replace Tyler Technologies if the facts lead us in that direction.”
Preckwinkle has said both the selection of Tyler and the decision to keep the company after earlier problems were made in agreement with the other elected property tax officials. Tyler’s current contract runs through March, and includes renegotiated terms that netted $4.3 million in county savings and tied future payments to the company hitting milestones.
In an emailed statement Monday, a Tyler spokesperson noted the company’s original contract was awarded “following a competitive evaluation process,” and that Tyler will continue to collaborate closely “with each of the participating agencies to ensure a successful outcome.”
Tyler has worked “around the clock for months” and honored that fixed-fee contract “even as we have surged resources, most recently over the course of 2025, in response to new data or changing directions,” the company’s statement reads in part.
Ald. Brendan Reilly, 42nd, speaks with reporters on Oct. 16, 2025, in City Council chambers at Chicago City Hall. (Brian Cassella/Chicago Tribune)
If Reilly were elected, he would not be sworn in until December, when the rest of Tyler’s to-do list would likely be complete. Further upgrades include the ability to issue $163 million in outstanding refunds and the operation of the county’s annual tax sale.
Preckwinkle otherwise defended her four terms leading the county at the Monday meeting, touting improved pension funding, balanced budgets, suburban infrastructure investments and criminal justice reforms that helped lead to the elimination of cash bail statewide.
Reilly, meanwhile, tried to tie her to the political success of former State’s Attorney Kim Foxx and Mayor Brandon Johnson. Foxx was Preckwinkle’s chief of staff and Preckwinkle helped Johnson’s first election to the County Board, but did not endorse his mayoral bid until the runoff. Reilly argued Foxx’s advocacy for bail reforms had placed the public at risk, citing the recent immolation of a Blue Line rider.
Preckwinkle said Foxx was an “excellent” chief of staff and “fine state’s attorney” who “put a lot of emphasis on trying to improve a system that was broken and that disproportionately impacted Black and brown communities in a negative way.”
“This terrible story about this poor woman on the Blue Line is heartbreaking, and my heart goes out to her and her family. But we can’t make public policy on the basis of these single horrific acts. We have to make public policy on the basis of data. And what’s happened in Cook County in the last four years is violent crime has gone down 50%,” Preckwinkle said, noting that she’d boosted the budgets of the state’s attorney, sheriff and chief judge in recent years and also spent money on violence prevention.
Asked about the mayor, Preckwinkle said, “I’m focused on my race and I have no comment.”
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