Something must be done to stop these ridiculous settlements
At what point do the taxpayers of Chicago get to say “enough is enough?”
So far in 2025, the Chicago City Council has approved over $145 million in police-related legal settlements — more than double what was budgeted — and the year isn’t even halfway over. That figure doesn’t include another $120 million in court-ordered payouts the city is challenging, nor the mounting legal fees, nor the flood of additional lawsuits waiting in the wings. By any reasonable measure, this is an atrocity — not of criminal justice, but of fiscal malfeasance and political cowardice.
Atrocities come in many forms. Some are moral, some judicial, and some — like this one — are budgetary. Chicago has turned the act of paying out settlements into a grotesque civic ritual, in which aldermen rubber-stamp multimillion-dollar payouts for decades-old incidents while shrugging at the burden it places on taxpayers, who had nothing to do with the original misconduct.
Let’s be clear: Legitimate claims of wrongful conviction, abuse, and official misconduct deserve redress. But the scale, scope, and timing of this year’s deluge defy all proportionality. The system has become a gravy train for lawyers, a reputational black eye for law enforcement, and an existential threat to the city’s financial stability.
A broken system, weaponized
As reported by the Chicago Tribune, the $145.3 million approved so far this year is already a record — and that’s not counting the $120 million federal verdicts that may still land on the books. Meanwhile, the city only budgeted $82.6 million for these expenses, which is itself a huge sum, but evidently not nearly enough.
Alderman Jason Ervin, ever the pragmatist, says: “There’s no real way around them.” That’s like an arsonist saying he has no choice but to call the fire department — after tossing the match.
Mayor Brandon Johnson’s budget director Annette Guzmán has called the situation “frustrating.” That’s one way to describe what happens when you ignore basic actuarial principles. Another might be “fiscally suicidal.”
Other cities, such as Los Angeles, have also struggled with backlogged lawsuits and uncapped damages. But here in Chicago, we take dysfunction and make it art.
Where’s the outrage?
From 2008 to 2024, Chicago shelled out $1.11 billion in police settlements and verdicts. Let that sink in. Over a billion dollars spent — not on public safety, not on education, not on infrastructure, but on lawsuits. Most of them traceable to a handful of disgraced cops like Jon Burge, Reynaldo Guevara, and Ronald Watts.
And more are coming. Watts alone is tied to at least 175 unresolved cases. The City Council recently approved $7.5 million for Ben Baker, who alleges Watts retaliated against him after he refused to pay a bribe. Baker spent ten years in prison. Is that worth $7.5 million? Maybe. But when you multiply that kind of payout by hundreds of cases, you get a bottomless sinkhole of liability.
The latest Watts case — one of several settled just this month — cost the city $1.2 million. In total, the May City Council meeting approved $62 million in settlements. And we’re not even at the summer recess.
The political theater of settlements
The City Council pretends to deliberate over these decisions, but it’s often just theater. The Law Department tells aldermen they’ll lose in court anyway, so they might as well settle. Corporation Counsel Mary Richardson-Lowry claims the city tries more cases than it settles. But in the high-dollar category? It’s deal after deal.
When Alderman Raymond López dared to suggest that maybe, just maybe, some tragic cases aren’t necessarily the city’s fault, he was shouted down. López pointed to a $5 million settlement for a woman who suffered frostbite after being left outside during a mental health crisis. Police allegedly failed to drive her to the station — one mile away. Tragic, yes. But is that a $5 million mistake? Or a systemic failure of mental health policy being pinned unfairly on Chicago Police?
Alderman Andre Vásquez blasted López and others, saying they’re gambling with taxpayer money. He’s wrong. What’s really happening is the city is hemorrhaging taxpayer money under the illusion that it’s saving it. Settling every case sends a message: If you sue, you win.
A cottage industry of opportunism
What has emerged is a cottage industry of litigation built around Chicago police settlements. Civil rights attorneys know the drill. File a suit tied to an infamous detective. Cite systemic failures. Wait for the settlement offer.
There is no risk because the city refuses to contest enough cases to establish a meaningful precedent. And while the Law Department pleads pragmatism, it’s also signaling surrender. By settling instead of fighting, the city invites more suits and higher costs.
The incentives are misaligned. The lawyers win. The city loses. The taxpayers foot the bill.
Budget bombs and political games
Every dollar spent on lawsuits is a dollar not spent on schools, parks, sanitation, or youth services. That’s not a theoretical trade-off. It’s real. Mayor Johnson wants to expand mental health programs and youth employment — two laudable goals — but they “pale in comparison” to lawsuit costs, according to the city’s own budget officials.
And still, the same progressives who want to spend more on social programs refuse to confront the legal swamp that is devouring the city’s finances. The contradiction is as obvious as it is shameful.
Chicago has only fully funded its police legal liability budget twice in the past 17 years. In 2018, the city set aside under $20 million. Today it budgets $82.6 million, and it’s still not enough. That’s not just poor planning — it’s institutional negligence.
What must be done
The solution isn’t easy, but it’s not impossible either. Here are a few common-sense steps that should be on the table:
- Stop blanket settlements. Every case must be scrutinized for merit. Tragedy is not always liability.
- Reform the Law Department. Bring in external audit and oversight of settlement strategies. Restore public confidence.
- Implement statute-of-limitations caps for non-criminal claims related to decades-old conduct.
- Push for state legislative reform to limit municipal liability in historical misconduct cases where the individuals involved are long gone or already prosecuted.
- Tie settlement approvals to individual aldermanic accountability. If you vote yes, you own the consequences.
- Prosecute attorneys and witnesses who file fraudulent claims. Yes, they exist.
And above all, inform the public. Every settlement should be made fully transparent, including a plain-language summary mailed to residents, outlining who got paid and why. If you’re going to write the check with taxpayer money, the taxpayers deserve to know.
A reckoning, overdue
This city cannot be run like a permanent apology tour. Yes, Chicago has a troubled history with policing. But bleeding the city dry isn’t justice — it’s self-harm disguised as virtue. Accountability doesn’t mean capitulation. And fiscal responsibility isn’t cruelty — it’s a moral imperative in a city already teetering on financial collapse.
The people of Chicago want safe streets, responsive police, and a government that spends money wisely. Right now, they’re getting none of the above.
Until something changes, expect more settlements, more deficits, more layoffs, and more excuses. And don’t expect a single one of the politicians writing these checks to be held accountable. They’ve already settled.
