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

What To Know This Week: Everyone’s worried about “scaring off the rich.” Meanwhile, South Side growers can’t get water in a heatwave, Medicaid data is being shared with DHS, and the state budget still leans on scarcity logic instead of taxing wealth.

3 Headlines:

1. JB’s Running.

From Playbook: Pritzker is about to announce he’ll run for a third term with a new 2nd in command. He’ll win. He’s got no real opponent. And his launch tour will be polished, well-funded, and filled with the usual Midwestern dad platitudes about fiscal responsibility and Trump being bad.

Pritzker’s spent the last year testing out presidential rhetoric at blue-state galas, throwing soft jabs at Trump, and posing as the responsible face of post-Biden liberalism. So what can he truly do in Illinois? The man who could lead a new generation of progressive governance could do a lot — and there’s incentive to make it happen while pushing back against federal attacks.

Why It Matters: Pritzker has the money, the mandate, and no serious opposition — which means the only thing stopping bold policy is fear. Fear of capital flight. Fear of progressive backlash. Fear of looking too left for a national stage he’s clearly eyeing. But if this is really the dress rehearsal for 2028, then he should act like it. Illinois could lead on fair wages, public investment, and progressive revenue.

2. Medicaid Data Handed to DHS

From the Sun Times: RFK Jr.’s agency shared Medicaid enrollee data—including immigration status—with the Department of Homeland Security.

The data transfer reportedly targeted blue states like Illinois, where undocumented residents can access care through state-funded Medicaid. Lawmakers like Chuy Garcia are warning it could lead to deportations, workplace raids, people dropping out of the system entirely.

The Illinois Department of Healthcare and Family Services says it never knowingly gave names, SSNs, or addresses—and wasn’t informed of the data sharing. But the feds aren't denying it happened. They’re just claiming it was legal.

Why it matters: Public health infrastructure is being repurposed as a surveillance tool. And if immigrant families can’t trust Medicaid, they stop seeking care — that’s the point.

3. Why South Side Farms Can’t Get Water

From Block Club: South Side community farms are growing fresh food for their neighbors on city-owned land—some on land the city gave them. But to water those crops, they’re stuck navigating a maze of permits, insurance forms, $950 hydrant cap fees, and aldermanic sign-off. In a heatwave, they’re hauling buckets and hoses across busy streets just to keep plants alive.

Why it matters: The fact that they still need political favors to access public water shows how deeply the logic of permission—who’s allowed to care for land, who’s allowed to feed people—still governs city systems.

Yes, progressives talk about “cutting red tape.” But the solution isn’t just deregulation—it’s re-centering who systems are built for. Because right now, the same city that greenlights NASCAR water hookups in days makes it nearly impossible for a Black-led garden to get a hydrant.

1 Big Question: So What Is the Progressive Revenue Plan?

As you know, my brain is rotted and decaying, so/because I spend too much time on X. There I get to have the world’s worst conversations with Chicago’s most esteemed Libertarian Influencers. As I am consistently reminded by my friends + others on the Left, this is a choice, once I should make far less.

But after really getting into it today post-Zohran win today about the Horrors that come from Taxing the Rich, I was really struck by how furious not groveling to billionaires made many, many ‘fiscally rational’ people lose it, telling me to go die for not praying to an effigy of Ken Griffin begging him to return and add more plaques to public buildings.

We don’t need billionaires to be generous. We need government to grow a spine.

And we can't tweet “tax the rich” into policy. But we can win:

• Real estate transfer taxes on luxury buildings (Bring Chicago Home almost did it)

• Financial transactions taxes (we are home to the literal derivatives market)

• Wealth surcharge models like NY and CA

• Estate tax reforms that exempt family homes and farms, not dynastic wealth

Zohran’s win is a win for governing cities well: unless we build political will to change that, every "balanced" budget will just reinforce inequality.

So, how do we do it? And how do I get off X?

2 Red Flags Stressing Me Out Today:

1. Zohran Mamdani!!!!

There’s actually nothing left to say about Zohran at 6 PM the day after the primary. The hot takes have completely circled back forth and all around — STILL. A few points I hope do not get lost:

His campaign isn’t just TikTok-savvy. It’s sharp, policy-led, and had strong organization. He’s talking about public housing, wage theft, antisemitism, and Palestine. The politics are clear — so is the precedent.

I’m not saying we all need to be Zohran. But we do need to stop pretending you can fix this moment by going quiet, waiting it out, or hoping for better donors.

Chicago: make more short form videos.

2. Ironheart is Fun and Made Me Less Sad

I’m cheating, this is not a flag. I’m tired. You’re tired. We deserve a break. Let’s watch Ironheart. It was filmed here, it looks fun, and is directed by Bronzeville director with homage to Eve Ewing (who wrote the comic). We all deserve someone building a flying robot suit in her garage and dunks on Tony Stark’s legacy. Hell yeah. I’m not that far in but no spoilers

That’s It This Week.

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Bonus Q: what’s the absolute worst Zohran take you saw today? Extra points if it’s a complete reversal of what the same pundit said yesterday….

_{All typos are intentional 4D chess.}