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Cook County Board President Toni Preckwinkle leaves after presiding over a board meeting on April 10, 2025. The Cook County Bureau of Technology and the procurement office that originally inked the contract with Tyler Technologies, are both under Preckwinkle’s office. (Eileen T. Meslar/Chicago Tribune)
Cook County Board President Toni Preckwinkle leaves after presiding over a board meeting on April 10, 2025. The Cook County Bureau of Technology and the procurement office that originally inked the contract with Tyler Technologies, are both under Preckwinkle’s office. (Eileen T. Meslar/Chicago Tribune)
A.D. Quig is a local government reporter for the Chicago Tribune. Photo taken on Wednesday, Feb. 26, 2025. (Eileen T. Meslar/Chicago Tribune)
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Cook County’s inspector general released a report Tuesday on the county’s troubled decade-long property tax system modernization, sharing some insiders’ candid — and wholly anonymous — reflections on what has gone wrong and estimating the county has so far spent $63 million on the project.

A “myriad of problems spread across all parties involved … created a ‘perfect storm’ and severely delayed the implementation” of the county’s new property tax system, which is still incomplete, Inspector General Tirrell Paxton’s office concluded.

The office reviewed the original contracts with Tyler Technologies and spoke to leaders of the county’s property tax offices and company officials from Tyler and two other contractors later brought on to provide oversight and project management.

Per office policy, the inspector general does not name the subjects of investigations, but the findings in Tuesday’s report echo an investigation into cost overruns and intra-office strife by the Tribune and Injustice Watch involving different Tyler contracts, as well as Tribune reporting over the past year on property tax problems.

Those problems have contributed to cascading delays of property tax bills being sent out to homeowners and property tax revenues landing in taxing districts’ bank accounts. There have been months of finger-pointing and the mess has cost tens of millions of taxpayer dollars.

Paxton’s office said the county had so far paid Tyler and the two outside contractors $63 million. That does not include the cost of maintaining the county’s old mainframe system, which totaled tens of millions more. The original contract with Tyler was approved in 2015 for $30 million.

Broadly, Paxton’s report found the inherent structure of the contract, the size and complexity of property tax data and separation between offices made implementation hard: “key functions are divided among separately elected officials whose offices operate with significant autonomy,” who saw senior staff turnover, shifting administrative priorities and slowed coordination.

Requirements weren’t fully hashed out at the start of the project, changed midway through and “were interpreted differently by each separately elected office,” the report said.

County office leaders also complained Tyler cycled through project managers and failed to dedicate enough staff to the project, while inside tax offices, the inspector general found the upgrade wasn’t always overseen by subject matter experts who could make sense of the county’s mainframe system or a smattering of auxiliary systems that had their own “unique formats, dependencies and historical practices” that weren’t written down.

“Nobody’s hands are clean. We fought for years, yelling and screaming,” one Bureau of Technology official said of the early phases of the project, according to the report. The bureau, and the procurement office that originally inked the contract, are both under the office of Cook County Board President Toni Preckwinkle.

The county’s Bureau of Technology eventually brought on an outside contractor to coordinate efforts. They should have done so sooner, the IG concluded.

In her written response to Paxton’s findings, Preckwinkle conceded that doing so “could have facilitated more efficient tax-administration implementation and stability,” but pushed back on other recommendations for procurement changes that would get the office more directly involved in managing performance.

Because of persistent problems, the county held back an estimated $15 million from Tyler over four years, according to the report.

Paxton’s report also concluded there was “evidence to suggest” Cook County Treasurer Maria Pappas’ office “has been less than fully cooperative” with implementation — Pappas has been the company’s loudest critic — and noted someone in the office “used highly offensive, demeaning and racially charged statements aimed at Contractors and County employees which delayed the project.”

Pappas previously fessed up to using strong language and threatening company leaders’ reputations, but told the Tribune any racially derogatory comments were taken out of context.

Tyler publicly blasted Pappas for “abuse” throughout the overhaul, eventually cutting her off from communicating with their staff directly. Paxton’s office recommended “sensitivity training” for “relevant officials and employees,” which Pappas agreed to, but only “on the condition that all county officials and employees also be required to undergo such training.”