Chicago's Future Is Union—If the Cops Don’t Bankrupt It First

Welcome to Chicago 312, your weekly hit of Chicago politics.

3 Headlines. 1 Big Question. 2 Red Flags. Every Week.

What To Know:
📚 Teachers just locked in a $1.5B win with 97% ratification—without striking.
🏠 City Hall says yes to Green Social Housing while the feds play dead.
🚔 And CPD blew through the annual misconduct settlement budget by April.

3 Headlines:

1. CTU Just Won a $1.5B Contract With 97% YES Votes

CTU just closed a $1.5B contract with CPS—ratified with a 97% YES vote.

Wins:
✅ Smaller class sizes
✅ 400 new aides
✅ 215 SPED managers
✅ 90 librarians
✅ Gender-affirming care
✅ Infertility coverage
✅ Paid bilingual training
And way more that I am definitely forgetting but is detailed extensively in the various articles I’ve linked to.

Though obviously I’m biased, this is a big deal: CTU has an organized, dues-paying, activated base—and the internal discipline to hold the line through pressure and national scrutiny.

Look — most political organizations in 2025 wouldn’t survive what CTU just pulled off. Many unions would never even attempt it. They’d split over messaging and coalition bickering, or cave on demands to chase approval. They’d pay too much attention to the ways that the right is incentivized to make them a scapegoat to derail labor power and public education. But CTU still bargained hard, held the floor, and delivered material gains in a moment where most institutions are busy “raising awareness” while getting steamrolled.

And this contract is not just a huge win, it’s a blueprint for surviving Trump-era governance. In a moment when Trump is dismantling the entirety of the federal government and breaking every rule to move faster towards authoritarianism, the CTU took risks and didn’t back down.

If we want to build this kind of durable, organized power elsewhere— especially RIGHT NOW — we need to stop hoping it’ll look prettier, cleaner, or more “unified.”

Want the deep policy nerd rundown on the contract? Check Chalkbeat.
Curious how this shifts day-to-day life for students? Sun Times has that.

2. Chicago is Building Green Social Housing From Scratch

More than 51% of Chicago renters are “cost-burdened,” which is a sanitized way of saying: they’re spending 30% or more of their income just to keep a roof over their heads and the lights on. At the same time, buildings pump out 70% of the city’s carbon emissions. This is the intersection of the housing crisis and the climate crisis, and it’s why Chicago’s moving forward with a Green Social Housing initiative.

• At least 30% of units will be permanently affordable for households earning up to 80% of the area median income. (This is the citywide mandate, if I’m not mistaken, but I’m waiting to confirm this with the Department of Housing).

• The city is putting $135M into a loan fund to keep construction costs down.

• A city-created nonprofit, the Residential Investment Corporation, will oversee development and retain majority ownership, so we’re not just handing everything to private developers.

• And crucially: this is all designed to work without federal funding. Now more than ever, something something — we can’t rely on federal funding.

Last week, Ald. Walter Burnett, Ald. Lamont Robinson , Ald. Angela Clay, and  Ald. Leni Manaa-Hoppenworth wrote an op-ed about the plan.

Read a more in-depth take from City Bureau’s Newswire.

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Bonus environmental justice headline: Hazel Johnson Environmental Justice Ordinance, named after the South Side environmental activist, is an ordinance that seeks to reform the city's planning and zoning policies and better protect communities from pollution. But advocates (included one quoted in the linked WBEZ article who called it “a weak piece of crap”) gathered today to call for increased community involvement in its development, demanding more in terms of enforcement.

3. Four months into 2025, we’ve already blown through the entire $82M budget for police misconduct settlements.

And there’s decades of torture, framing, and corruption that the city still hasn’t paid for.

Mayor Johnson says he “inherited quite the mess.” He’s not wrong.
👁 More than 200 lawsuits are still pending—naming disgraced cops like Jon Burge, whose records of horrifying misconduct are literally taught in public schools. These aren’t “he said/she said” cases. These are known monsters, with stacks of wrongful convictions under their belts.

Still, right now, there’s no citywide plan for a global settlement. No systemic fix. Just a new division in the Law Department to “look at the cases.”

Can Chicago put limits on this department that’s been bankrupting the city’s budget and trust for decades?

Read more from Heather Cherone at WTTW.

1 Question:

I think this video of Brandon Johnson challenging Trump is one of the best moments of his term.

If “not kissing the ring” is the baseline, what does a proactive anti-fascist strategy actually look like for Chicago, especially as federal funds dry up?

2 Things Troubling Me:

1. A Chicago man was deported to an El Salvadoran prison, his family says:

   From WBEZ: “Once we start using wartime authority with no oversight, anything is possible. Anybody can be picked up.”

   Check out this guide from Mejiente breaking down the phases of the President’s tactics criminalizing immigration and how deportation is being wielded as a political weapon.

2. Emotion-Hacked by AI: This article from the American Prospect has probably freaked me out as much as anything in terms of the purely technical move to fascism. We’ve moved to entire AI narrative economies built on emotion-hacking: these videos are ridiculous to look at, but they’re emotionally satisfying, algorithmic masterpieces. It’s clear that we need so much more than the standard political content ecosystem from progressives right now. Otherwise, the future is destined to be written by whoever is churning out those 1800 Barron Trump + Golden Retriever videos every day.

_{All typos are intentional 4D chess.}