Welcome to Chicago 312, a newsletter on Chicago municipal politics, institutional power, and how the city actually works. This is the weekly roundup: 3 Headlines, 1 (Existential) Big Question, 2 Red Flags. If someone forwarded you this, welcome! Subscribe here.

This week: Johnson wrote an executive order that O'Burke immediately refused to enforce, Cook County still can't figure out how to send Chicago its property tax money because of a decade-long tech disaster, and Logan Square told delivery robots to fuck off.

Let’s get into it.

3 Headlines:

1. O'Neill Burke Continues Innovative ‘Ignore’ Electoral Strategy

Mayor Brandon Johnson signed an executive order January 31 directing CPD to investigate and document crimes committed by federal immigration agents, creating a framework for police to identify, document, and refer federal agents for prosecution when they violate state or local law. Johnson's order says that, under "direction of the Mayor's Office," CPD will refer evidence to Cook County State's Attorney Eileen O'Neill Burke's office for prosecution.

O'Neill Burke's response: absolutely not. In an email to staff Friday, O'Neill Burke said her chief assistant sent a memo to the mayor's office calling the executive order "not only wholly inappropriate, it also jeopardizes our ability to effectively prosecute and secure convictions when federal law enforcement agents have committed a crime."

The problem? Johnson's order requires CPD supervisors to make felony referrals "at the direction of the mayor's office." O'Neill Burke's office warned that defense attorneys would characterize any prosecution as political and attempt to discredit CPD witnesses by suggesting their investigation was directed by the mayor's office. Mayoral staff who gave directives could be called as witnesses, "creating serious litigation issues."

And on Tuesday, Johnson backtracked, saying his order "does not necessarily" involve his office in potential charges despite the text explicitly saying it does. He said the order will remain as-is, but claims he won't actually be directing which cases get referred.

Why It Matters: A prosecutor who built her career defending the police isn’t suddenly going to start prosecuting federal agents for immigration violations — unless her hand is forced. And there are options here, considering her track record. City Bureau reports that between January and mid-May 2025, her office incarcerated nearly twice as many people at first appearance hearings as 2024—despite no increase in arrests. By mid-2025, Cook County Jail population exceeded pre-Pretrial Fairness Act levels, even as violent crime dropped 12% statewide. Clearly O’Neill Burke has no problem locking up residents pretrial at record rates — but she won't prosecute ICE agents violating sanctuary law.

O'Neill Burke won by 57,000 votes in 2024. She's up in 2028. If immigrant rights groups, labor, and community organizations make this a litmus test, and say that her refusal to prosecute federal agents violating sanctuary law is a re-election issue, the political calculus changes.

But right now, she refuses without consequences.

2. Cook County's Property Tax Disaster Forces Johnson to Split Pension Payment

WTTW reports that acting CFO Steve Mahr, Budget Director Annette Guzman, and Comptroller Michael Belsky told the Finance Committee Monday that the city couldn't afford to make a full $260 million advance pension payment because Cook County was months late sending hundreds of millions in property tax revenue.

Johnson's initial 2026 budget proposed a $120 million advance pension payment. The City Council rejected that and required the full $260 million to avoid another credit rating downgrade. Johnson allowed that budget to take effect without his signature, then paid half the pension advance and promised the rest later.

Opposition aldermen immediately accused him of defying the City Council's will. But in this case, the problem isn't Johnson sabotaging their budget. It's Cook County being unable to deliver property tax revenue on time because of a disastrous contract with Tyler Technologies.

Cook County has paid Tyler over $85 million since 2015—nearly a decade into a contract that was supposed to take four and a half years—and the system still doesn't work. County Treasurer Maria Pappas has called it "possibly the worst technology contract Cook County has ever written." 

As county officials describe it: "Tyler fixes one thing, breaks another." The company was supposed to complete the project in four and a half years. It's been nearly ten. Tyler's Illinois business license was revoked in September 2025 for failing to file annual reports.

Why It Matters: Tyler Technologies is genuinely fucking up Cook County's cash flow, and it’s the kind of weird drawn out municipal procurement drama that is both incredibly boring and a huge dramatic mess. That's not Johnson's fault.

But here's what's funny: Waguespack demanded Monday's hearing because he suspected Johnson was sabotaging the alternative budget by delaying the pension payment. Then Johnson's team explained the Tyler Technologies disaster—which is real!—and Waguespack just... believed them. "I agree with the explanations," he said, as if the guy who just spent months fighting Johnson's revenue proposals suddenly trusts Johnson's budget office to tell him the full truth about cash flow.

The real test is whether the second half gets paid—and when. If "later" keeps getting later, or if Johnson uses Tyler's continued failures as justification for indefinite delays, Waguespack will have helped Johnson prove the alternative budget doesn't work by accepting his excuses for not fully implementing it.

Tyler Technologies is a legitimate disaster. That doesn't mean Johnson isn't using that disaster strategically.

1 Big Question: How Are You Thinking About Online Organizing and Offline Resistance?

Last week I asked if you were still on X. This week I'm curious about something muddier: the relationship between online organizing and offline resistance.

Two anonymous thoughts:

Here's my thinking: The internet is a tool, not real life. I use it to learn what's going on, read analysis, and find out about actions. Crucially, I also use it to meet real people. But once I'm out in the real world, the internet is tangential. No one I've met on ICE whistle patrol has been someone I met first on the internet. Same with my poetry reading series—few attendees are people I met online (though the readers always are). Online and offline should inform each other, but it's a balance.

I keep thinking about this Machiavelli reference: "In Discourses on Livy... Machiavelli cautions against seeing technology as a military panacea, as a way of freeing warriors from the harsh realities of killing and the dangers of being killed; and from the discipline, skills and qualities necessary for success on the fields of battle." Technology, like any tactic utilized in an organizing campaign, is valuable—but is not the same as (nor does it replace the need for) strategy. Online and offline organizing have to build on each other.

More experiments in this section soon.

2 Red Flags: 

Boring Bureaucratic Leverage for Trans Rights

Sam Ames wrote a piece this week explaining something I didn't fully understand: how public comment on federal regulations can be real leverage. Right now Trump's HHS has proposed three anti-trans rules (cutting Medicaid/CHIP funding for gender-affirming care, punishing hospitals that provide it, excluding gender dysphoria from disability protections).

When federal agencies propose regulations, they're legally required to read and respond to every single public comment before finalizing the rule. The teams doing this are small—often under 10 people—which is why when the Department of Education's Title IX regulation protecting LGBTQ+ students received 235,000 comments, processing took nearly 2 years. Current submissions: 2,000-3,000 comments total. Go read Sam’s piece and gum up the administrative process.

Hopeful Read of the Day

If you’re depressed: J.P. Hill wrote a piece about "the banality of good" that's worth reading. Here’s the link.

"We got so used to the scary, mundane evil of this country and this world that we came close to forgetting that millions and millions of people are willing and eager to fight the good fight every single day."

That’s it this week.

Well, here’s something fun from national news, I guess:

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