Tyler Technologies CEO Accuses Pappas of Obscene Tirades

The tech meltdown snarling Cook County’s property tax pipeline has spilled into a full-blown public brawl.

The CEO of Texas-based Tyler Technologies accused longtime Cook County Treasurer Maria Pappas of subjecting his executives to bullying, threats and “obscenity-filled tirades,” according to a copy of a letter the company sent to the Treasurer’s office obtained by WBEZ and reported in the Chicago Sun-Times. The nine-page letter marks a dramatic escalation in a dispute over a yearslong effort to modernize the county’s property tax system, a project that has already cost taxpayers hundreds of millions of dollars.

In the letter, Tyler CEO H. Lynn Moore Jr. blasted what he called Pappas’ “scapegoating” of the company for delays that have held up billions in property tax distributions to schools and other local governments. He accused the treasurer of showing a “lack of accountability” for her office’s own missteps while trying to “deflect blame and divert attention.”

The bulk of Moore’s complaint, though, focused on Pappas’ conduct. He alleged that Tyler staffers endured repeated verbal attacks over the past year and said the situation had deteriorated to the point that company executives would no longer take her calls or meet with her in person.

Moore also said Tyler raised concerns with other county officials, including aides to County Board President Toni Preckwinkle, only to be told the behavior amounted to “that’s just Maria being Maria.”

Pappas has for months publicly blamed Tyler for technological failures that delayed as much as $8 billion in tax revenue at one point. The backlog has strained cash flow for public agencies, especially Chicago Public Schools, which has said the holdup cost it at one point last year roughly $250,000 a day and forced it to tap a line of credit, racking up interest costs and pension-related expenses.

The delays also left thousands of homebuyers waiting on property tax reimbursements tied to late tax bills, injecting more friction into an already tight housing market.

Pappas, who has held the office since 1998 and is running unopposed in the March Democratic primary for an eighth term, and has also declared her intent to run for Chicago mayor in 2027 after the 2026 treasurer election, did not apologize. She told WBEZ she was furious that tens of thousands of taxpayers were owed refunds and cited her reputation as combative.

“The whole world knows that Maria Pappas is an attack dog,” she said, adding that she would not tone it down.

Preckwinkle called the allegations “troubling and unacceptable” and said the matter would be referred to the county’s Department of Ethics and Human Rights.

Beyond the personal fireworks, the standoff highlights the stakes of public sector tech overhauls. Three Cook County and Illinois agencies have paid Tyler about $250 million for upgrade efforts that have been plagued by delays and overruns, according to prior reporting by Injustice Watch and the Chicago Tribune. So, for local governments reliant on predictable tax flows to fund payroll and debt service, the dysfunction is more than political theater and a costly upgrade — it’s a liquidity problem.

— Eric Weilbacher