High taxes, bloated budgets, the botched Tyler Technology deal, Kim Foxx, Brandon Johnson...the list goes on and on
In late 2024, when she was a guest on WBEZ's Reset with Sasha-Ann Simons, Toni Preckwinkle, in her role as president of the Cook County Board of Commissioners, was discussing property taxes in the county, and after telling the host that the “system is broken.” She added, “We have a system that benefits property tax lawyers.”
Seriously?
Preckwinkle is a colossal hypocrite.
Toni is also the chair of the Cook County Democratic Party. And the Chicago vice-chair of the county party is Springfield’s worst legislator, pension plan-destroyer Robert F. Martwick, who happens to be a partner at a law firm that specializes in property tax appeals.
Fortunately, in March, when she faces voters in the Democratic Primary, Boss Toni can be sent packing. For the first time since she was elected board president in 2010, she faces a strong and well-funded primary challenger, 42nd Ward Chicago alderman Brendan Reilly.
For decades, first while Preckwinkle was simply a ward committeeman, and then into the beginning of her time as party boss, then-Chicago alderman Edward Burke was chairman of the slate making committee in charge of endorsing Cook County Democratic judicial candidates.
And all that time Burke was a name-partner at a law firm that specialized in property tax appeals.
In early 2018, Burke hosted a campaign fundraiser for Preckwinkle at his Southwest Side home. As scrutiny of Burke’s legal problems increased, Preckwinkle resisted calls to return the $116,000 collected at that event — she finally did so a year after the fundraiser.
Burke served 10 months in federal prison for his crimes.
Other powerful Democrats who were cashing in on the property tax game as lawyers were longtime state House Speaker and Illinois state party chairman Michael J. Madigan, who is now a federal inmate, and former state Senate president John Cullerton.
Of course, Preckwinkle never spoke out against any of them as they enriched themselves from the Cook County property tax system.
Soaring property taxes
In November, Cook County residents received their tax bills. Homeowners living on Chicago's South and West Sides were shocked when they saw astronomical increases in their property taxes.
For instance, property taxes skyrocketed 82 percent in Englewood, 99 percent in North Lawndale, and 133 percent in West Garfield Park.
Overall, property taxes in Cook County have increased 10 times the rate of increase in property values.
Plans to fix property tax problems gone awry
What brought Preckwinkle to that 2024 appearance on Reset was the release of a report from the county’s Property Tax Reform Group. It’s a long read with many recommendations. Have any of them been carried out? It appears none of them have.
Another Property Tax Reform Group study was released in December.
And don’t be optimistic that any of these recommendations will be implemented. Because in 2018, Preckwinkle and then-Cook County Assessor Joseph Berrios, who was chairman of the Cook County Democratic Party at the time, commissioned a study that declared residents in poorer areas of the county were overburdened by their property taxes compared to owners in better off parts of Cook.
Thanks to Preckwinkle and others in Cook County government, things have gotten even worse for poor people who own homes.
Let’s recap: The 2024 study has been gathering dust for over a year, and Preckwinkle told Simons on Reset that she had been working with the Cook County Board of Review and the assessor’s office on this property tax problem “together since 2021.” Apparently by that time the 2018 study had been shelved.
Cook County property taxes are a complicated mess and it’s quite apparent hack politicians like Preckwinkle and Martwick, and many others of course, enjoy the rotten status quo.
Try, try, and fail again.
Preckwinkle’s lottery scam
On the infrequent occasions when a reporter asks Preckwinkle about what she calls “a broken system,” she brags about the $1,000 property tax relief program — which goes to only 13,500 of over one million county homeowners, as the Contrarian’s Paul Vallas explained on X.
Her much-touted $500 guaranteed income payments to 3,250 impoverished county residents is a drop in the bucket, because 450,000 residents fall into that low-income level to qualify for them.
To qualify for those programs, eligible county residents enter a lottery, which is fitting, because winning Preckwinkle’s raffle is about as likely as collecting big money in the Illinois State Lottery.
State lotteries thrive because they bolster unrealistic financial dreams. False hopes fuel Preckwinkle’s crumbs of property tax relief.
Toni’s games of chance are cruel publicity stunts, because when county residents learn about them, they mutter to themselves, "Choose me, choose me, choose me!" And when they aren’t picked, they hope for the best the following year, when they very likely won’t get chosen again.
The 11-year long Tyler Technologies nightmare
The second installment of the 2025 county property tax bills were mailed several months later than they were supposed to be. Blame goes to Tyler Technologies, the politically connected IT firm that was supposed to modernize and streamline Cook County computer systems. The county property tax portion of their work began in 2015 and was supposed to conclude in 2019.
In a Christmas Eve news dump editorial, the Chicago Tribune editorial board perfectly captured debacle of the tardy bills.
"Cook County Board President Toni Preckwinkle has taken all too little ownership of this fiasco, given that she was the driving force behind contracting with Tyler in the first place — beginning a decade ago — and opted to continue with Tyler in 2020 after initial results were bad. Cook County Treasurer Maria Pappas, whose office is responsible for compiling the tax bills and distributing the proceeds, mainly has blamed Tyler and Preckwinkle for her office’s struggles doing that job. Cook County Assessor Fritz Kaegi largely has blamed Tyler for Chicago property assessments that were reported late to the Illinois Department of Revenue in 2025. Preckwinkle’s office has said that Pappas is responsible for the tax distributions to the local governments."
In mid-January, the Tribune reported the delay in mailing out property tax bills has cost school districts at least $122 million. Again, that’s just the school districts. Think of those unforeseen expenses as a backdoor tax hike.
Cook County’s undetonated lawsuit bomb
Another backdoor tax hike that could cost Cook County — and the rest of Illinois — is continuing to kick the can regarding not changing the law regarding delinquent tax property sales. Public officials have known since 2023 the current system of tax sales in Cook County has been ruled unconstitutional. In a 2025 Chicago Contrarian podcast, Jim Bosco said the resulting class action lawsuit could end up costing Cook County — which of course means Cook County taxpayers — $1 billion, plus legal fees. Considering that the current county budget is $10 billion, this is, to paraphrase the great 20th century senator from Illinois, Everett M. Dirksen, “real money.”
For perspective, it’s important to note that in 2011, Boss Toni’s first year as board president, the Cook County budget was just $5 billion.
Where does all that money go? “The far left that has been ushered into office under Toni Preckwinkle’s leadership has been conducting lots of social experiments that … are very expensive. They’re hard for us to afford, and we’re not even sure if there’s any kind of return on investment,” Brendan Reilly told the Chicago Sun–Times last year.
Powerful public officials who are truly answerable to answerable to constituents use their bully pulpits to inform taxpayers of an impending financial storms, or better yet, prevent them from even happening. But that is not Preckwinkle, even though, as heroin dealer Virgil Sollozzo phrased it in The Godfather, Boss Toni carries politicians in her pocket — people such as Rob Martwick—"like so many nickels and dimes.”
She could have stopped the bleeding. But Boss Toni made the bleeding worse.
Preckwinkle simply dithers, and fails, unless you count her advancement of her far left agenda as a success.
What to do
If Preckwinkle says she needs more time to fix Cook County’s broken property tax system — and everything else that plagues county government — don’t fall for her hokum. Remember, she’s had 16 years to repair the damage.
Time’s up, Toni.
Democratic voters in Cook County need to vote for Brendan Reilly.
Early voting begins on February 12.
