Cook County Treasurer Maria Pappas held stock for years in a company with a major contract working in her office, a potential violation of the county’s conflict-of-interest rules.
Pappas has been one of the most vociferous critics of Tyler Technologies, the company that has been in charge of the rocky upgrade of the county’s property tax system, for more than a decade. Tyler has been embedded in the treasurer’s office, which calculates and mails out property tax bills, for years.
The problematic rollout of Tyler’s tax system revamp within county offices led to late property tax bills last year and problems distributing property tax revenues in recent months to local agencies like schools and libraries.
But while she was hammering Tyler, Pappas owned stock in the company. Pappas’ office shared statements from her broker that show 10 Tyler shares were purchased in 2020, and four more in 2022. Together, they cost $4,562. Tyler first received the county contract in 2015.
Pappas said she was not aware of the investment, which was made by a former broker, and sold them in March of 2024. And following a Tribune inquiry, she also sold stock for other companies doing business with the county, including the bank providing lockbox and collection services for the treasurer, her office said.
Those investments were some of the 30 to 40 assets, including individual stocks and exchange-traded funds, that Pappas disclosed in annual statements of economic interest between 2021 and 2024. Under state law, officials are required to disclose those worth more than $10,000.
Even though the holdings were less than $10,000, Pappas’ office said she reported them anyway “in the interest of transparency,” but suggested she did not review them closely.
“When she realized they were in her portfolio, she instructed her new broker to sell the shares immediately,” spokesman Michael Puccinelli said of the Tyler stock in an emailed statement. She submitted her economic interest statements without noticing Tyler on the list, he said, and when she did, she asked her new broker to sell.
After the Tribune asked this week about the Tyler stock or other holdings that potentially represented a conflict, Pappas sold stakes in Microsoft, CDW and JP Morgan, according to her office. JP Morgan has a contract with the treasurer’s office to allow taxpayers to pay property taxes at Chase Bank locations, process fees and fines, and make online payments and remote deposits.
CDW provides IT infrastructure equipment countywide, and the county broadly uses Microsoft for its operating system.
Puccinelli said Pappas didn’t realize she held the stock from the other county contractors until the Tribune asked about additional potential conflicts. All the stocks Pappas held were for amounts below the $10,000 disclosure threshold, but she disclosed them anyway, according to Puccinelli.
“It was a mistake and a learning experience. She should’ve been aware of this and wasn’t,” the statement from Pappas’ office said.
The county’s ethics ordinance states no county official can use their position “to influence any County governmental decision or action” if that person “knows, has reason to know, or should know” that they or a relative has “any economic interest in such action or decision.”
Pappas didn’t have direct hiring or firing power over Tyler. The project was overseen by the Bureau of Technology under Cook County Board President Toni Preckwinkle’s office. But Pappas and other county officials whose offices dealt directly with the property tax system were consulted on contract extensions, and were in charge of executing Tyler changes in their offices.
The threshold for what “interest” means in the county’s ethics ordinance “is confusingly written,” Alisa Kaplan of the watchdog group Reform for Illinois said in an email. The ordinance seems to use financial and economic interest interchangeably. While “economic interest” includes anything of value in monetary terms, financial interest is more specific, including something in which the owner “currently received or is entitled to receive in the future more than $1,200 per year” or “with a cost or present value of $5,000 or more.”
The Tyler sale yielded $5,865 for a net profit of $1,303.
“It appears that Pappas would only be violating the law if she were making official decisions about Tyler while her interest in the company was worth $5,000 or more. It’s not clear that that ever happened. If it did — if the value of her Tyler stock rose to over $5,000 at some point while she was participating in decision making about the company — we’re talking about a pretty small number above the threshold here,” Kaplan wrote, suggesting the ordinance needed clarifying.
Juliet Sorensen, a former member of the county’s Board of Ethics and the director of the Rule of Law Institute at Loyola University, said even if her broker managed her investments day to day, Pappas reasonably should have known what she held, given her position and the annual requirement to report holdings.
The $5,000 and $10,000 discrepancy could have been a source of confusion, Sorensen said, but she could have asked the ethics board for advice, including about whether she was required to disclose those potential conflicts to them.
“What is the treasurer’s office in the business of?” Sorensen said. “Should she know the county does business with JP Morgan? I think so.”
A spokesperson for Tyler said they were not aware of Pappas’ holdings and “do not have access to ownership held by individuals.”
At the time of the first purchase in March of 2020, Tyler had just hit a major milestone: $1 billion in revenue. The stock price was about $277.
By that time, Pappas had been railing against the company for months, saying in a November 2019 letter it had blown deadlines, cycled through project managers and driven up ancillary costs. She concluded “it is long past time to cancel the contract with Tyler Technologies, possibly the worst technology contract with a vendor that Cook County has ever written.”
Just before the second stock purchase in January 2022, Pappas had written to Tyler’s CEO to chastise the company for being “four years late” on its work in her office and express her skepticism that any of its future timeline goals would be met. By then, the stock price was up to $470.
Just after the third stock purchase in May of 2022 — a single share for $376 — the county extended Tyler’s contract with new guardrails tying payment to goals being met. Pappas had written to Preckwinkle opposing its passage, saying it “would be throwing good money after bad and should be rejected.”
Top Tyler leaders haven’t been thrilled with Pappas either, replying to her letters by defending their work and characterizing her correspondence as counterproductive and at times, misleading or hyperbolic.
Pappas is running for reelection as county treasurer, a post she’s held since 1998. She has no challengers in the March 17 Democratic primary, and has floated running for mayor in the 2027 election.
