Waste of the Day: Chicago Is Late on Taxes

A “perfect storm” of convoluted bureaucracy caused Cook County, Illinois to spend 10 years and $63 million building a property tax billing software that did not work. 

Because tax collection was delayed, Chicago Public Schools were forced to take a loan to stay operational, incurring $33 million in interest costs.

Why Chicago and Cook County were late collecting property taxes

Key facts: A July 21 report from the Cook County inspector general found that the contractor designing the tax billing software, Tyler Technologies, received conflicting information from three different government agencies involved with the project.

The county Assessor’s Office helmed the first stage of the project. But when a new assessor was elected, he added new requirements that delayed the project.

The Treasurer’s Office gave input later on, and asked Tyler Technologies to use different home ownership data than the Assessor’s Office had provided, according to the IG report.

The Treasurer’s Office staff also reportedly argued with Tyler Technologies about how to design the tax billing software. This created an “openly adversarial” work environment, according to the audit. At one point, county staff were told to intentionally withhold necessary data from Tyler Technologies, the report stated.

Eventually, the county hired another contractor just to serve as a liaison between government officials and Tyler Technologies.

The county also required Tyler Technologies to hire a local project manager, but the first three managers departed because of “knowledge gaps or interpersonal conflicts with county employees,” according to the IG report.

Software riddled with errors

The Treasurer’s Office began using the new tax software in late 2025, even though the county’s Bureau of Technology warned that there were “hundreds of errors.” County homeowners have still not received their 2025 tax bills as of Aug. 8, 2026.    

The Clerk’s Office and Treasurer’s Office said Tyler Technologies did not assign enough staff to the project, and that its programmers were not always present at meetings about technical issues, the report states. But the audit also noted that Tyler Technologies’ staff sometimes voluntarily worked seven days a week and without pay to try and resolve issues with the tax system. 

Background: Cook County Treasurer Maria Pappas makes $122,534 as of 2024, per Open the Books’ database. She has held the office since 1998 and plans to run for Chicago mayor in 2027.

Summary: Chicago’s property taxes are already among the highest in America. Wasting money trying to send out the tax bills adds insult to injury. 

This article was originally published by RealClearInvestigations and made available via RealClearWire.