Welcome to Chicago 312: 3 Headlines. 1 Big Question. 2 Red Flags. Every Wednesday. Subscribe here.

What To Know This Week — Cook County doubles down on police impunity, Illinois bans AI therapy before it does more harm, and the Tribune continues to make bad private equity driven choices that leave them without a film critic.

Pensions are also back in local headlines, with the same question as always: what is a pensionwhat will it take to make progressive revenue a reality?

What do we need to do to make it viable for the state to tax the rich?

Let’s dive in.

3 Headlines:

1. Dexter Reed’s Family Isn’t Giving Up

The Triibe: Cook County State’s Attorney Eileen O’Neill Burke announced she will not charge the officers who killed 26-year-old Dexter Reed, claiming “the facts and law” make prosecution impossible. Her office hasn’t released the full ballistics evidence to the family — even as it leans on those same tests to justify the decision. Former COPA chief Andrea Kersten already questioned whether Reed’s stop was even legal; Stroth, the family’s lawyer, calls it an unconstitutional pretext that ended with CPD firing 96 shots in 71 seconds.

Why It Matters: O’Neill Burke ran as a “moderate” after Kim Foxx — and is already governing in a way that reinforces police impunity. Declining to prosecute a case rooted in an unlawful stop fits the pattern: protecting CPD first, leaving families to fight in civil court. The message is clear: under O’Neill Burke, Chicago’s violent police never see a courtroom.

2. Illinois Bans AI Therapy, Which… Makes Sense

WBEZ’s Reset: Illinois just joined Utah and Nevada in banning AI for mental health care. Regulating AI is a cluster, btw: it’s developing and being used so much faster lawmakers can react, so this is a big deal both in terms of mental health care policy annnd trying to crack down on the robot takeover.

There’s been a wave of cases across the country where bots (both ChatGPT and more closed system therapy app type AI) seemed to push people deeper into crisis: one New Yorker said ChatGPT convinced him he could fly if he just believed hard enough. Another UCSF psychiatrist has treated a dozen patients spiraling into psychosis tied directly to prolonged AI use. There are actually TOO many examples to link to them all, a sign that things are really going well in many different parts of society.

Why It Matters: Illinois’ mental health infrastructure is already starved, and politicians are tempted to plug holes with cheap “AI therapy.”

Kelly Hayes wrote a great piece about AI, addiction, and how nefarious this tools can be. One short insight: chatbots are built to validate, not challenge. Which means when you tell one you’re Jesus, or that you can fly, it nods along. Banning AI therapists is basic harm reduction until there’s oversight and accountability. (And definitely listen to the longer conversation from Reset).

3. Michael Phillips Departs the Tribune — A Media, Civic, and Labor Problem

Axios Chicago: For the first time since the Siskel era, Chicago has no chief film critic after Michael Phillips took a buyout offer from Alden Global Capital, the company that owns the Tribune.

Statehouse reporter Ray Long left earlier this summer after decades covering Illinois power. Lizzie Kane, who had been covering housing, took a buyout too — though she was later rehired to cover housing after everyone made fun of the Tribune about this. Right now, Alden (who owns the Tribune) has clear priorities: keep bleeding staff, shuffle beats, and then somehow expect profit.

The staff Guild called the buyout terms that led to Phillips leaving insulting, and warned that Alden Global Capital’s ownership model is to cut until there’s nothing left.

Why It Matters: The Tribune’s editorial board, who I obviously have beef with, has a clear agenda; punching down on progressive revenue, labor, and city government. Meanwhile their newsroom , which is supposed to cover those same fights — labor, housing, culture — is being hollowed out. With every critic, beat reporter, or watchdog gone, Chicago loses part of its ability to cover what’s happening in the city. That’s the real story of Phillips leaving: not just the end of an era, but the shrinking of what Chicago remembers.

Also Watching:

• Protests Around The Man Trapped in the Bean — I have nothing to say about this. Hope they keep on doing their thing? (Sun-Times)

1 Big Question: What is a Pension and Why Is it Kicking Chicago’s Budget in the Teeth?

Last week, Governor JB Pritzker signed the Tier 2 police/fire bill (HB 3657). It boosts Tier 2 Chicago police and firefighter benefits to match downstate systems and complies with federal Social Security rules. The city’s analysis says this almost certainly worsens Chicago’s 2026 budget gap and puts more pressure on the city’s credit rating. Importantly: there’s no state money included, so the buck lands on Chicago when we’re already in a fiscal hole. The best write up is (as usual) from Heather Cherone at WTTW.

A pension is deferred pay for workers. You earn it now; your employer owes it later. Most workers no longer have pensions because corporations dumped them — but that doesn’t mean public workers shouldn’t get pensions. Chicago’s problem isn’t that pensions exist, it’s that the city underpaid them for decades, because they’re politically painful to fund. The fight is about who actually pays.

Think of it like hot potato — except instead of tossing a potato, they’re tossing a $36 billion bill, and surprise: it’s still hot, and now it’s kicking the city’s credit score into the dirt. Uh, but it’s also a buck, that we passed (too many mixed metaphors in this edition, sorry), because politicians skipped payments for years.

At any rate, any fix in this buck/potato game has to include progressive, recurring revenue that’s sized to the problem: service/professional-services taxation authority, closing high-end loopholes, PILOTs for wealthy tax-exempts, and—someday soon—running the constitutional fight for a graduated income tax or a millionaire surtax with earmarks for transit and schools.

We can’t waste another year without finding new revenue — not just for pensions, but for schools, transit, and public services.

Questions: What am I missing here? Who else should I be talking to? What else do you want to know (in a longer deep dive) about what’s up with pensions across the board?

2 Red Flags Stressing Me Out Today: 

1. Zohran’s Win Means Making Politics (and the Internet) Not Suck

 Defader: Everyone is going to read this deep dive from Corey Atad on the Zohran campaign. Before we talk about communciations, let’s be clear that what made Mamdani’s campaign work was in no small part because of their field team — the 50,000 volunteers knocking 1.5 million doors. The videos worked because they were tethered to organizations (the DSA, Working Families, and many others) willing to grind.

Mamdani is proof of concept that politics is entertainment now, and that maybe, that doesn’t have to be a bad, disrespectful, or corrupt thing. The counterpoint to the awful flywheel of the right is respecting the fact that no one owes you their attention.

Why It Matters: Mamdani’s campaign treated video as part of the infrastructure.. You couldn’t open your phone without seeing him. Chicago movements could do that. We already have the raw material: better ideas, stronger institutions, and the willingness to knock the doors.

But IMO there is still struggle when it comes to truly investing in winning attention and seeing that world as part of the battleground — one that catches so many people who will never show up at a meeting, unless we can figure out how to reach them in a way that respects who they are and what they can offer movements.

2. Gaelic Rapper Faces Terrorism Charges

The Guardian: Mo Chara — one third of Kneecap, the Irish rap trio — was back in Westminster Magistrates Court today facing charges of terrorism for shouting slogans during a London concert in November 2024, potentially punishable by up to 14 years in prison. Since his last court date, Israel has killed 9,000 Palestinians in . The British government, which arms and backs those war crimes, is pouring its energy into labeling an Irish rapper a “terrorist.”

Why It Matters: Language scares empire. I like Kneecap’s music. Even if Democrats still avoid the word genocide, there is resistance internationally and in Israel.

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Quick Ask:

In six months of experimenting, Chicago 312 has gone from “an email I send sometimes, when I remember” to reaching 50–60K people a week across social platforms, 500+ subscribers, and mentions in Convergence and The Triibe, and many, many replies from angry libertarians on X.

And after a decade of messing around with social media, political writing, and a lot of trial-and-error, the focus of Chicago 312 — dynamic, progressive, Chicago-centered content across channels — feels like it’s hitting in a different way.

The 312 probably has 4–5x the audience of most Chicago organizing groups I’ve worked with because it’s filling a void that I’m finding (at least in my contract work, which I will always keep doing) to be really hard for other groups, politicians, or even media outlets to fill — one that starts to compete with the flywheel of right wing media without pushing a specific (funded) political agenda.

Where I’m at: I realized that if we actually want to break the local media flywheel, and compete with groups like Illinois Policy in people’s feeds, it’s going to take more.

It means investing in video, working with other groups, and experimenting with format, live events, and real structure for this thing, including fundraising. And — probably — asking YOU what you want to see.

BTW, a teaser for that first video podcast is live right now: an interview with Maya Dukmasova of Injustice Watch on why Chicago’s courts are not Law & Order — plus some Chicago specific “Would You Rather” Qs to keep it fun.

Okay, here’s the ask:

👉 Will you subscribe to the Chicago 312 YouTube channel?

That one click tells the algorithm this project is worth pushing out to more people — and it helps me figure out how far this experiment can go.

Thank you for reading, sharing, and arguing with Chicago 312 — I’m grateful for everyone who’s been here for this ride.

See you next Wednesday.

H