Property tax system is broken but it remains a cash cow that keeps government growing along with Cook County Democratic Party’s political machine
The recent move by the Cook County Democratic Party to oust County Assessor Fritz Kaegi should come as no surprise to sober observers of Chicago politics. A political smokescreen designed to shield Cook County Board President and Democratic Party Chair Toni Preckwinkle from real accountability for the Tyler Technologies debacle — Kaegi ran afoul of Preckwinkle for publicly criticizing a public contract with the tech firm. The price tag now stands at a staggering $265 million, with costs still climbing.
This fiasco simply underscores Preckwinkle’s 15-year tenure as board president and seven years as party boss — years in which she has failed to enact the fundamental reforms Cook County’s property tax system desperately needs.
Power plays and political retribution
Preckwinkle has developed a pattern of targeting and unseating incumbents who dare defy her wishes. Take, for example, her campaign to remove Clerk of the Court Iris Martinez in the 2024 election. Martinez’s offense? Seeking transparency around the SAFE-T Act by publicly releasing accurate data on pre-trial release and court no-shows. In orchestrating Martinez’s defeat, Preckwinkle backed Mariana Spyropoulos — a major party donor — who outspent Martinez by a ratio of 26-to-1.
The blame game: Tyler Technologies and tax delays
Kaegi, once an ally of Preckwinkle — he even supported her handpicked candidate for Chicago mayor, Brandon Johnson — has now found himself at odds with her over delayed property tax bills. Preckwinkle blames Kaegi's office for missing assessment deadlines; Kaegi, in turn, points to the county’s costly commitment to Tyler Technologies, which has been plagued by technical failures and repeated delays.
The original contract, heavily influenced by entrenched political interests, has ballooned beyond control. Five years ago, county leadership even considered terminating the agreement, but instead doubled down and continued funneling money into an already ailing project.
Ignoring transparent warnings
Preckwinkle’s refusal to course-correct is evident not just in her disregard for Kaegi’s concerns, but also for those voiced by Cook County Treasurer Maria Pappas. Pappas has long been the county’s most transparent voice on property taxes, warning repeatedly about the Tyler upgrade. She has reported that, due to these issues, her office cannot distribute roughly $216 million to 2,200 agencies or issue $56 million in refunds to over 25,000 property owners.
Delays are so severe that Pappas cannot send out the second installment of tax bills — a situation that only compounds financial strain for taxpayers, ultimately generating more revenue from late payment penalties.
A crisis for homeowners
Since 2007, Cook County property tax bills have soared 78 percent — a rate 10 times higher than residential property values — forcing homeowners to pay, on average, $2,558 more annually while their property values stagnate. In 2025 alone, tax bills skyrocketed nearly 20 percent in some south suburban communities, disproportionately impacting Black families and driving many to sell homes they can no longer afford. Today, Illinois residents as well as businesses pay the highest property taxes of any state in the country.
The so-called property tax relief caps are but an illusion
Yes, Illinois has property tax caps. However, the caps have massive loopholes. They don’t apply to Home Rule cities and counties like Chicago and Cook County. They don’t protect property that has been reassessed or improved. They allow school districts to recoup money lost in property tax appeals. The significant amount of revenue from late payments and finds are exempt from the cap. Finally, caps don't protect taxpayers from tax rate increases tied to TIF property tax diversions.
Structural inequities and the TIF trap
The property tax system is doubly unjust, not only due to the flawed assessments and an arcane appeals process but also because of unchecked expansion of Tax Increment Financing (TIF) districts. Though TIFs were designed to spur development in blighted areas, today they siphon $1.8 billion from the tax base, driving effective tax rates ever higher.
Chicago Public Schools alone have raked in $1.9 billion in TIF windfalls since 2019, in addition to their substantial share of standard property tax collections. Most of these surpluses are not targeted for relief where it’s needed — they simply bolster the budgets of taxing entities with little regard for fairness or accountability.
Gimmicks over relief
Rather than using the $100 million-plus in penalties collected from late payments to offer genuine relief, the county rolled out a one-time, highly publicized program, distributing just $15 million to about 13,600 homeowners, while spending $1.4 million on yet another politically-connected firm to administer the relief. More than a million homeowners and renters remain completely excluded. Why not rebate all of the windfall to those most burdened by this failed system?
Profiting from a broken system
Cook County's broken property tax system is the cash cow that keeps government growing and with it Cook County’s Democratic Political machine.
Example: Preckwinkle’s Democratic Party Co-Chair, State Senator Bob Martwick, is a practicing attorney, and his own law firm brings cases before the tax appeals board — the Cook County Board of Review. Preckwinkle placed Martwick on every committee she created, including the committees that select judges from the Circuit Court to the Illinois Supreme Court. In this role, Martwick has extensive influence over the selection of Board of Review Commissioners and judges that his law firm comes before.
The real cost of inaction
Now, Cook County faces a convergence of crises: A property tax apparatus in disrepair, an unfair burden on middle- and lower-income families, and leadership incapable of reform. The ongoing dysfunction comes as Mayor Brandon Johnson — himself a Preckwinkle-backed candidate —appears unprepared to tackle Chicago’s multiple budget gaps, totaling at least $1.7 billion for the city and its public schools, without again turning to property taxes.
Toni Preckwinkle, joined by her legislative allies, has had ample time and opportunity to simplify and reform this broken system. Instead, Cook County’s property tax conundrum has deepened, leaving residents to bear the consequences while political leaders evade responsibility. The question now is: Will voters finally hold Preckwinkle, and those complicit in this dysfunction, to account? They will soon have their chance.
