Welcome to Chicago 312, your weekly hit of Chicago politics: 3 Headlines. 1 Big Question. 2 Red Flags. Every Week. Subscribe here.

What To Know This Week: Durbin and Schakowsky are out, the CTA’s in crisis, and immigrant families are back in legal limbo.

3 Headlines: Major Retirements, CTA Funding, ICE

Schakowsky and Durbin Are Out: The Fight for the Future is On.

Congresswoman Jan Schakowsky is retiring after nearly three decades representing IL-09, kicking off a rare, wide-open primary in one of the bluest, safest House districts in the country.

Senator Dick Durbin is out too. At 80, the Senate’s second-ranking Democrat says it’s time, setting the stage for a generational battle over one of the most powerful seats in Illinois politics.

Illinois Democrats are facing a double void of institutional power (maybe triple, depending on what happens with Danny Davis), and everyone from Rahm Emanuel to Daniel Biss is reportedly eyeing their shot.

Who will replace them? In IL-09, progressive challenger Kat Abughazaleh isn’t just running to replace Schakowsky—she’s calling the bluff on Democratic gatekeeping. She raised $400k in two weeks, called for more people to enter the race, and offered direct campaign support to anyone who wants to run against her.

Elsewhere, Jason Friedman is already challenging Danny Davis in IL-07, and Nick Uniejewski is taking on Sara Feigenholtz in the state Senate over racist remarks and generational rot.

With fascism rising nationally and an affordability crisis gripping Chicago, the stakes are too high for passive succession. This moment calls for vision, clarity, and serious ground games.

“Doors Closing”: The CTA’s Crisis Is a Chicago Crisis

The L is the circulatory system of Chicago, and it’s on the verge of collapse. Tal Rosenberg’s piece for Chicago Magazine is the definitive overview of how we got here, why it's bigger than Dorval Carter, and what comes next, whether that’s a revamped agency, a revived tax base, or a total freefall.

Ridership is down nearly 50%, federal funds are almost gone, and without new state funding, we’re looking at layoffs, closed stations, and CTA service slashed to less than the transit budget for Madison, Wisconsin. If you ride, organize, or care about housing, jobs, or the city’s future at all: this is essential reading.

Read Newswire's longer piece and ways to take action here.

Chicago’s Venezuelan Community in Limbo Amid Trump’s Push to End Deportation Protections

From Borderless: Trump’s DHS tried to end TPS for Venezuelans—again—under the excuse of “national security,” aka racist fearmongering. A federal judge blocked it (for now), but the damage is done: families are retraumatized, workplaces destabilized, and more quiet terror for people waiting to see if they get to stay in the city they call home. It’s a gut check on how quickly rights can be erased—and how fragile safety really is, even in a Sanctuary City.

1 Question: Housing Crisis No One Wants to Touch

Nowhere to Go by brilliant reporter Devyn Marshall Brown, for the Chicago Reader, is one of the most damning pieces I’ve read on housing in Illinois for a long time. Right now, people who’ve already served their time are now forced into homelessness, prison-by-another-name, or corporate-owned reentry limbo. If you care about housing, reentry, abolition, or basic constitutional rights, you should read this.

2 Things Troubling Me: Despair and Digital Security

“If you still care, then I think there's still potential for this situation to be turned around.”

Sarah Kendzior has been warning us for a decade about how authoritarianism actually works, and has a rare ability to name what’s happening while making the stakes clear. This conversation with Kelly Hayes is a clear, steady look at how we are seeing the erosion of empathy—and what it means to hold onto our humanity anyway.

Digital security that’s “good enough”

Margaret Killjoy’s take on threat modelling doesn’t talk down, catastrophize, or overcomplicate, which is rare. It balances urgency with agency, reminding us that every +1 shield matters, and that imperfect precautions are still worth taking.

That’s It for This Week.

We're watching a generational shift in Chicago politics, a fiscal cliff for public transit, and a housing system that treats people like trash. But we’re also watching organizers push back, challengers step up, and everyone in Chicago say: this is our city.

📨 Forward this to a friend who always gets stuck on ghost buses,
🧵 Reply with your takes and questions,
🔗 Subscribe if you haven’t yet.

PS — As I was finalizing this, Pritzker announced that Illinois will be defunding investments in companies controlled by El Salvador to punish the country for holding American residents without due process. More of this…

_{All typos are intentional 4D chess.}