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

No time for an introduction— too many things happened in Chicago this week. Let’s go!

3 Headlines:

1. What Happens When ICE Raids Are No Longer in the News Cycle?

Block Club: In the span of a week, the legal façade holding up Operation Midway Blitz, Trump’s deportation machine in Chicago, started to crack.

On Wednesday, a judge ordered the release of more than 600 people arrested in the so-called “Operation Midway Blitz,” saying their mandatory detention was illegal under immigration law. Hours later, six Chicago activists—including congressional candidate Kat Abughazaleh and Commissioner candidate Cat Sharp—pled not guilty to conspiracy charges for blocking an ICE van at Broadview. And Thursday morning, ICE quietly released Diana Santillana Galeano, the North Center preschool teacher whose horrifying arrest inside a North Center daycare went viral, ruling that her detention was unlawful.

And a ProPublica investigation published this morning pulled the curtain off the most theatrical—and hollow—episode of “Operation Midway Blitz,” a midnight South Shore raid where 300 federal agents rappelled from a helicopter, detonating flash-bang grenades, zip-tying residents, and detaining 37 people, almost all Venezuelan asylum seekers, while a camera crew filmed. The White House claimed it had captured “terrorists” from the Tren de Aragua gang, but ProPublica traced 21 of the detainee: none charged with crimes, most had no records at all.

All of these legal developments, and the total lack of public buy in for the South Shore raid, is a sign that any legitimizing legal plan or narrative for “Operation Midway Blitz” is on it’s way out — especially with Border Patrol commander Greg Bovino reportedly leaving Chicago.

So what happens now that this narrative campaign is out of myths and legal pretense— but also out of the news cycle?

Why It Matters: First: this ALL happened because Chicago fought back, and fought back hard. The city was organized, people refused to shut up, and retirees with whistles chased unskilled out of their depth military agents with whistles every. single. day.

If you had said to me in September, “is Chicago (or any place in this country) equipped to stand up to a federal force taking over their streets?” I don’t know that I would have said yes — but I am so inspired by that collective defense and everyone who participated in it, in every way.

And now the news cycle will move on. The cameras will leave the North Side and Little Village and Broadview. That’s part of Trump’s plan nationally, undoubtedly: siege politics that outlast whatever coverage and resistance comes about and then swings back around.

People are still detained, still have legal fees, still have been profoundly impacted in horrible ways. The big, cinematic raids will quiet down, replaced by quieter, more targeted operations: traffic stops, courthouse arrests. Homeland Security is already signaling appeals, and will look for easier entry points — partnerships with Cook County sheriffs, data-sharing through state agencies, anything that doesn’t look like a raid and is less high profile. And there has been limited conversation about what CPD officers could do in the face of these federal agents.

You’ll hear less about it — and that’s the point.

So this next stage is a political test for the city (and state) leadership: the city’s sanctuary infrastructure has leverage — but only if officials use it. The city could codify stronger local protections, refuse cooperation requests, and expand rapid response networks. Or it could declare victory and move on, which is exactly what the feds are counting on.

2. Tax the Rich, Ignore the Drama

CBS: On Tuesday, Ald. Byron Sigcho-Lopez confronted Gov. JB Pritzker on progressive revenue in Ald. Mike Rodriguez’s ward during a conversation about his constituents in Little Village who have dealt with ICE’s presence.

When it escalated. state Sen. Celina Villanueva stepped in, and Pritzker tried — and failed — to walk away cleanly. It was all very weird — but it felt especially weird to do such an intense stunt about… taxes. (Though Sigcho-Lopez clarified later that this was also in part because of the Governor’s role in the state police supporting ICE).

Why it Matters: So much of what I’ve heard people talk about regarding this moment has been framed around JP v. Sigcho Lopez, or “is it ok to do performative stunts in other people’s wards” and “hey!! leave Mike Rodriquez alone!!”

On top of that, the politics and history of the 20th Ward are a rich text I’m not equipped to expound on in a sidenote.

But I want to talk about the actual content of this weird conversation, because both sides made interesting points on an under covered issue: progressive revenue.

Illinois is locked into a flat tax — one of only 14 states with this model, and the most regressive in the country — which means cities like Chicago have no legal authority to tax high-income individuals. Every year with the current state laws on taxing the rich, Chicago is forced to propose municipal revenue Band-Aids in its budget.

This year’s budget has a major (and unusual) tax proposed on corporations — and Pritzker made an unusual move by condemning it publicly.

When confronted by Sigcho-Lopez, Pritzker said that he fought for the Fair Tax in 2020, which is true. This amendment to the constitution would have created a graduated income tax, raising $3.6B/year and taxing only the top 3% of earners, but it failed because Ken Griffin, who no longer lives here, working hard to work to control state politics with his money, spent $54 million to kill the amendment.

But things have changed since 2020: New Yorkers just made Zohran Mamdani mayor after he campaigned explicitly on doing this.

Nationally, support for a wealth tax stays above 60%.

And Illinois has no political path towards progressive revenue — in a moment when it’s needed and incredibly popular.

3. The Shutdown Ended. The Health Care Crisis Begins.

WBEZ: The longest federal shutdown in U.S. history is over. After 43 days of furloughed workers, stalled food aid, and airports on skeleton crews, Congress let the expanded Affordable Care Act tax credits expire, the only thing keeping health insurance remotely affordable for 24 million people. And though SNAP benefits will now resume, when these credits disappear on December 31, premiums will spike by $700–$1,700 a year in Illinois — and as many as 90,000 people could lose coverage. As WBEZ reports, one woman says her premium will jump from $343 to over $1,200 a month, so she’s booking as many medical screenings as she can before Dec. 31.

Why it Matters: Here’s a quote from the article because I haven’t seen much other in depth coverage of how bad this is:

“What should we do?” Seyed says during an interview with his wife Shahin in their home. The couple asked that their last name and where they live be withheld because of privacy concerns. “I said to her, ‘I mean, we have to be realistic: We can live only, maximum, 10 more years.’”

These subsidies worked. They cut the uninsured rate to record lows and proved that direct public spending makes health care cheaper. The fix is popular — build a public option. Otherwise — we’re left with this system, one where people are scheduling their deaths around the political mechanisms of Congress.

1 Big Question:

On the day of the shutdown ending, Washington Rep. Marie Gluesenkamp-Perez introduced a resolution to rebuke Rep. Jesús “Chuy” García over a ballot-access maneuver tied to his chief of staff’s entry for his seat—framed by MGP as a “free and fair elections” issue, a hypocritical “election denial… on our side of the aisle.” This was quickly signal-boosted by national reporters and young progressives, and people like David Axelrod shared it immediately.

It was a pretty clear off-ramp from her own controversial vote to end the shutdown .

When Rep. Delia Ramirez condemned this weird politically motivated attack, it blew up among many young progressives online who said it was ‘idpol at its worst” to defend Chuy Garcia against this resolution. For the last 24 hours, I’ve seen thousands of people online support Marie Glusenkamp-Perez.

Seeing this dominate the national news cycle without context, having watched it develop in Chicago’s right wing X discourse until it got legs enough for national feels truly frustrating. It doesn’t mean the critiques aren’t valid but it’s weird to see so few national pundits ask:

“Why now?”

“Why MGP?”

“Who benefits?”

This isn’t meant as a defense of Chuy or this kind of move. But this particular cycle felt like a new wave I've never seen from the 'local to national' social media echo chamber -- the right and center in Chicago blew this up until it hit a young progressive YIMBY adjacent crowd, then MGP ran with it. Worth watching.

2 Red Flags Stressing Me Out Today: 

1. 🚨 Oh My God, Don’t Bail Out Chat GPT

   Hard Reset: OpenAI says it doesn’t want a federal safety net — but a leaked letter shows it asked the White House for loan guarantees to “de-risk” AI manufacturing, days after its CFO floated the idea of a “government backstop” for the company’s trillion-dollar compute buildout.

2. 🚨 Starbucks Workers Strike Across the Country:

   AP: Today, on ‘Red Cup Day,’ one of Starbucks’ busiest sales days, more than 1,000 baristas at 65 stores nationally walked out. Workers at stores (including in Chicago) said the company has stalled contract talks, built intentionally austere scheduling, and union-busted by closing stores.

   More on what happened at Chicago locations in the Tribune today.

Finally…

This week started off a new Chicago 312 segment on movement communications: what’s working, what’s not, and how we can actually build narrative power together.

The first one: What Campaigns Keep Getting Wrong About Creators.

It helps me cover everything happening (and build much better quality content) when you share: