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

What To Know This Week — Trump’s logistics for occupying Chicago are now on paper, what it really costs to not fund transit, pressure on hospitals about gender affirming care, and why Chicago doctors who worked in Gaza are calling to ‘block the bombs’.

Let’s dive in.

3 Headlines:

1. No One in Chicago Wants the National Guard 👍

WTTW: Trump’s using Chicago as a punching bag: at a Friday press conference, he promised the National Guard would come here next after his D.C. deployment. He called the city “a disaster” and “a killing field” even though crime is down 21% compared to last year and nationally, Chicago isn’t even close to the top of the list for dangerous cities (we’re 16 out of 30). BTW, Trump keeps blaming “Chicago’s no bail policy,” one of the best meaningful reforms to state law in the last decade: Illinois ended cash bail in 2023, and a year later the data showed no increase in violent or property crime.

Trump has broad control over D.C. because it’s a federal district — but not Chicago. In response, Governor Pritzker took the water taxi to a press conference with Mayor Brandon Johnson + everyone who has ever thought about running for office, saying that they are ‘raising the alarm’ and telling Trump no one wants the National Guard in Chicago.

Today, Trump’s plan to “take control” of Chicago now has logistics: an email shows DHS, ICE, and possibly National Guard troops will be housed at Naval Station Great Lakes for a month starting Sept 2. Federal agents have already been drilling there with riot shields and flash-bangs. This is real prep for a federalized occupation, not a trial balloon.

Why It Matters: Trump is selling Chicago as chaos to people who don’t live here, don’t care about here, and want to see us punished. If he puts troops here, it won’t be about safety. It will be about proving that fear runs the show, and whether he can use the federal purse + federal force to override state leaders and intimidate blue cities.

2. Rogers Park Tenants Unionize After Massive Rent Spike

Block Club: Tenants across five Rogers Park buildings formed the Fuerzas Activas De La Damen tenant union after a new landlord — Ark Management’s Imran Khan — jacked up rents by as much as $500. With eviction notices looming as early as Sept 1, the union, backed by the All Chicago Tenants Alliance, is even open to a rent strike. Longtime residents—some who've lived there 20–40 years—are fighting back.

Why This Matters: This is about churning long-time, lower-income residents out of one of the last North Side beachheads of affordability. If the union holds the line—through public pressure, code enforcement, and coordinated rent action—it sets a template for beating this model. If they get steamrolled, expect copycats across the city. The signal Chicago sends in Rogers Park is the policy.

3. The Transit Cliff Costs More Than Funding Transit Does

Streetsblog Chicago: Saving CTA, Metra, and Pace costs billions — but letting them collapse costs far more—lost jobs, declining household income, and cratering regional growth. Gutting $771 million from CTA, Metra, and Pace service in 2026 means 40% fewer buses and trains. That translates to 72 million lost rides a year, 181 million extra car miles, and $200+ million dumped into traffic, pollution, and crashes. Healthcare access craters, physical activity drops, and thousands more trips to the doctor get missed. TLDR: Transit collapse costs 70% more than fixing it.

Springfield already has a bill on the table — new revenue from ride-hail and delivery surcharges. Both fees more than pay for themselves because of the external costs cars already impose. And yet lawmakers left session without passing it, knowing a “downward spiral” of service cuts and fare hikes is baked in.

Why This Matters: Transit is the backbone of Chicago’s economy. Every delay, every stall, every punt from Springfield costs us — in time, in wages, in health, in literal cash. Lawmakers know funding transit is an economic slam dunk. When they say “we can’t afford it,” what they mean is “we’d rather risk gutting the system than tax the people who actually can afford it.” We already pay for collapse—through longer commutes, worse jobs, and fewer opportunities. And in October, the Illinois General Assembly will hold its Fall Veto Session — the final window to pass funding and reform legislation for 2026.

 In other words: train.

1 Big Question: What Does Sustained Resistance Look Like As Things Get Weirder?

Monday’s presser outside Trump Tower was the easy part. Pritzker, Johnson, Duckworth, Durbin — all saying the Guard isn’t welcome. Good.

But press conferences don’t stop ICE vans from pulling up downtown or the National Guard.

So what does sustained resistance actually look like in Chicago — from everyone, but especially from the elected officials + groups that were in full form on Monday?

Legal: Illinois will file suit, probably fast, which is good — it creates friction and delays and raises the cost of Trump’s stunts. California’s still tied up in court over the deployment of the National Guard in LA.

But lawsuits alone are delay tactics — by the time a judge rules, Trump has his B-roll.

Fiscal: Illinois sends far more money to Washington than we get back. Illinois taxpayer dollars are paying for militarization while Springfield is scrambling to plug a $771 million transit hole.

Politicians (both in office and running) should be hammering this daily: if federal dollars flow through Illinois, they belong in transit and schools, not in ICE vans or National Guard bunkers

Labor: Hamilton Nolan wrote more about this today: only thing that jams an authoritarian occupation is work stoppage. Unions are trying to scale this up — a Labor Day ‘Workers Over Billionaires’ rally at Haymarket is already planned as a counter-show of force: a test of whether leaders can unify around something bigger.

If the federal government really is planning to occupy Chicago with our own tax dollars, the real test for Illinois leaders isn’t another press conference.

It’s if they can build sustained resistance beyond lawsuits and budgets: refusing cooperation, cutting off local resources, and backing the wider network of workers, neighborhoods, and institutions that can actually make an occupation unworkable.

2 Red Flags Stressing Me Out Today: 

1. Chicago Doctors Returning From Gaza Demand Lawmakers ‘Block the Bombs’

 WBEZ: Chicago area doctors came back from Gaza with stories of bombed hospitals, kids with amputations, and parents begging for water. Their warning: don’t look away, and don’t let politicians shrug off responsibility.

They are meeting with Illinois lawmakers to demand support for Rep. Delia Ramirez’s “Block the Bombs” bill — legislation that would limit U.S. arms sales of the deadliest weapons to Israel.

Some lawmakers are moving: Reps. Chuy García, Jonathan Jackson, Danny Davis, Jan Schakowsky, and Robin Kelly have signed on. Tammy Duckworth even broke ranks in the Senate to block a weapons transfer. But others — Underwood, Foster, Quigley, Casten, Schneider, Krishnamoorthi — are stalling, offering platitudes about formula shipments while avoiding the bill itself. Ahmad called a meeting with Underwood “by far one of the worst” he’s ever been in.

Why It Matters: Will Illinois’ delegation follow constituents in a state with the country’s largest Palestinian diaspora?

2. Michigan AG Warns Hospitals: Don’t Capitulate to Trump on Gender Affirming Care

Erin Reed: Hospitals in blue states have been quietly folding their gender-affirming care programs as the Trump administration has threatened funding cuts, investigations, and even bogus “genital mutilation” charges against providers. This week, University of Michigan Health became the latest to cave.

But Michigan Attorney General Dana Nessel fired back! She warned UM that dropping care to appease Trump could violate Michigan’s nondiscrimination laws — calling the move “shameful, dangerous, and potentially illegal.”

Why This Matters: Nessel’s warning reframes the fight: capitulation isn’t neutral or easy, it’s illegal. If more attorneys general follow her lead, hospitals and universities will be forced to resist instead of retreat. Without that pressure, “safe state” promises are meaningless.

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Thanks for reading, sharing, and yelling back at me in the replies — all of it keeps this thing alive. We’ll be back next Wednesday with more, and full podcast interviews are on the way.

Until then: if someone tells you Chicago is a “killing field,” you have universal permission to explain the street grid to them until they cry.

H

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