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

What To Know This Week — There’s so much math today! The transit cliff is real, hospitals are wobbling, and the tax code is.. well, it’s bad and we don’t about that enough. But we can all agree that no one cares what Donald Trump thinks about not having cash bail in Illinois.

Let’s dive in.

3 Headlines:

1. After deploying the National Guard in DC, Trump keeps threatening Chicago.

What Happened: Trump ordered roughly 800 National Guard troops onto D.C. streets and asserted federal control over the city’s policing—a wildly authoritarian step that the White House framed (lazily) as a crime crackdown or something. D.C. was “easy” legally because the D.C. National Guard answers to the president, not a governor.

Since we at Chicago 312 have major interest in (and major anxiety about) the media propaganda flywheel of the right, I will share the shortest possible version of how this happened, from Garbage Day. This is what he calls — LOLgislation:

“The 19-year-old DOGE recruit who called himself “Big Balls” on LinkedIn was reportedly attacked by two 15-year-olds. The next day, Trump posted a photo of [DOGE teen] to Truth Social, saying, “If this continues, I am going to exert my powers and FEDERALIZE this city.” At the press conference on Monday, Trump used what appeared to be a chart by the X account @EndWokeness to justify declaring a state of emergency in a city with historically low crime rates.”

This, of course, is both historically how authoritarianism gets legitimized, and profoundly racist. It feels important to me to say that every hero quoted about this on local DC news was funnier than any Republican has ever been in this life. (It’s also worth reading the rest of that Garbage Day email about politicians and social media in 2025).

What Was Said About Chicago: In the same breath, Trump vowed to “end no-cash bail” in Illinois (which… actually works, a long time progressive organizing win) and floated a National Guard surge to Chicago, calling the mayor and governor “incompetent.” The president does not control the Illinois National Guard and cannot simply send troops into Chicago.

Pritzker said Trump has “no legal ability” to send troops here and Mayor Brandon Johnson said ‘seriously, what is wrong with this guy’ in so many words, pointing out that this is part of Trump’s intentional attacks on Black Mayors in blue cities.

Why It Matters: Trump is SO SCARED of Chicago, and SO SCARED of Illinois.

All of these federal cowards are. He can’t control Chicago or Illinois, and he’s so, so scared about that. Trying to manufacture a crisis and legitimate more takeovers is disturbing on every level but it’s also a sign of his deep, deep fear. This is a region he doesn’t run and can’t fully bully on every political level: city, county, state, House, Senate.

In many ways, in particular when it comes to deportation, his attempts to retaliate create real horrifying suffering. But it’s also where he’s most likely to overextend and lose.

Chicago is a city of haters first and foremost, united by this across neighborhood, race, class, and opinion on the Bean. Whatever bickering or criticism around everything else in politics here, it will take more than posturing for Trump to actually challenge that power. Try it.

2. The 2026 transit fiscal cliff looms.

What Happened: Without new state money, RTA projects a $730–$770M yearly hole. Worst-case planning is up to 40% service cuts—which is basically a tax on working-class time. If Springfield punts again, City budgets get squeezed harder by the fallout. And by the way… as Streetsblog says here while dunking on the Tribune Editorial Board, it really is a crisis.

WBEZ says — lawmakers missed a key deadline, and CTA/RTA are now planning around cuts if the gap isn’t filled — scenarios include eliminating up to four L lines and 65+ bus routes, with a regionwide “40%” as the doomsday case. RTA’s latest update says 2026 budgets are being built assuming a 20% gap, which can still translate into 40% cuts without new revenue.

Why It Matters: Want a concise case for funding? Check out Ald. Anthony Quezada and State Sen. Graciela Guzmán pushing a “Hot Transit Summer” and calling for action before veto session.

3. Hospital Deserts

WTTW: Weiss Memorial in Uptown has shut most operations; CMS terminated its Medicare status over repeated safety failures. Local leaders are scrambling and patients say they learned about the shutdown from community groups, not the hospitals. Nearby West Suburban Medical Center is facing a similar crisis. Safety-net systems that rely on Medicaid are warning they can’t absorb more shocks. And this is just the beginning…

Why It Matters: You don’t need a PhD to know “depending on an ER that’s further away = worse,” but this is the predictable end of federal cuts + thin margins + bad owners. But it is fixable policy, not an act of God.

Also Watching:

• Firefighters’ union reached a tentative deal after four years in big Chicago labor news (Block Club)

• CHA’s “Plan for Transformation” turns 25 and could take 40 more years to finish at current pace (Block Club)

1 Big Question: Is Illinois’ regressive tax system really the “crime of the century”?

Spoiler alert: yes!! Here’s what we can do about it.

The City is staring at a ~$1.1–$1.2B 2026 hole. Springfield just juiced police and fire pensions in a way that adds billions to long-term costs for the city. While everyone is freaking out about funding these long term commitments, it’s important to remember that Illinois makes the poorest residents pay the highest share of their income in state/local taxes, while the richest pay the lowest.

Everyone’s yelling about what to do next, and the mayor called Chicago’s overall finances a “point of no return.” It’s in this context that yesterday, Chicago’s CFO Jill Jaworski called that messed up part of our tax system the “crime of the century.”

Illinois (and Chicago) have been staring at these budget issues forever - after decades of underfunding reality, something had to give. Now the question is how we pay, and who.

Why it’s like this (and why Chicago gets squeezed)

Illinois taxes are backwards: richer people pay a smaller slice of their income than everyone else (that’s what “regressive” means).

If you make about $25,000 a year, roughly 19 cents of every dollar you earn goes to state and local taxes. If you make $250,000+, it’s about 11 cents of every dollar.

ITEP’s Who Pays? found Illinois is among the most regressive states — low-income families pay roughly double the effective tax rate of the top 1% (before we even talk transit fares or fees).

In Chicago, many flat taxes are inequitable — but county property taxes in particular hit Black and Latino homeowners harder (ABC7), with appeals and commercial breaks shift the burden back onto working people.

Why don’t we just ‘tax the rich’?

Let’s dispel one of the many damaging + delusional political stories about what is unpopular in this moment:

People don’t want more flat taxes. People DO want to tax the rich.

Chicago and Illinois are under-collecting at the top and over-taxing the bottom, and it is long past time to change this. There is popular support for this.

But here’s the thing: Illinois’ constitution forces a flat income tax, and changing this requires a constitutional amendment. Progressive organizers (and JB Pritzker) fought for this, but (in part due to Ken Griffin pouring money into trying to control the state government before he decided to sulk away to Florida) it didn’t pass.

That doesn’t make the current system fair — or even mean that voters don’t want us to tax the rich (especially with everything that has changed in the last 5 years, and the grift of Trump and DOGE will only make this more apparent).

It just means that a real structural fix to the messed up tax system will be a long (and statewide) political fight. But Chicago isn’t totally without options when it comes to finding new revenue this year that isn’t regressive as hell.

What CAN we do?

Here’s what we can do (and have to do) right now for Chicago’s budget this year, then the long term existential options.

Right Now (Chicago): Here’s a breakdown of all of the current revenue options on the table for this Budget season from Axios. Some of these raise real money (Axios lists $297M for garbage, $305M for services), but they hit different people very differently.

Long Term (Springfield): A graduated income tax would fix the state’s backwards math, so Chicago isn’t forced to balance budgets on riders, renters, and classrooms. And that means running the Fair Tax campaign to amend the constitution again with broader backing (labor + hospitals + transit + education + mayors).

The CFO also argued the state needs: A professional services tax: with clear carve-outs around healthcare and childcare, a low-income credit, and municipal sharing. Equity relief that would expand the state EITC/child tax credit and create a renter’s credit to blunt the unfair tax burden while the big structural fixes move.

AT ANY RATE, if we keep balancing Chicago on a state tax code that taxes groceries harder than wealth, we’ll keep cutting buses, swelling class sizes, and pretending that’s “responsible.” If Illinois fixes the code and Chicago picks recurring, progressive revenue, we stop committing the “crime of the century” and start funding this city so it’s livable for everyone.

2 Red Flags Stressing Me Out Today: 

1. UK age checks just went live

EFF: The UK’s Online Safety Act was implemented, which means that users of platforms like Reddit, Discord, Bluesky, X must now comply with “highly effective” age checks through things like ID uploads, facial scans, etc. Age checks at this scale are privacy-invasiveand exclude people without government ID; they also open doors to face-scan bias and centralized data risk, with no proof they actually keep kids safer.

Why It Matters: The US is moving the same direction. In June, the Supreme Court allowed Texas’s porn age-verification law to take effect, signaling friendlier courts for state-level mandates. Expect copycat bills soon.

2. Invasive shrubs now dominate 80% of our forests

Block Club: Conservationists say aggressive non-natives (buckthorn, honeysuckle, et al.) have taken over nearly 80% of Chicago-area woodlands, choking biodiversity, worsening flooding, fewer birds, fewer pollinators, and more soggy basements.

Why It Matters: Plant nerd stuff is nice to me even when it’s climate collapse adjacent news. But, of course, plant nerd stuff also = public safety + climate resilience. Forest Preserve ecologists say removal needs ongoing maintenance (fire, cutting, herbicide, replanting) or the shrubs bounce right back. One more place where we need to get the money…

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See you next Wednesday.

H

_{All typos are intentional 4D chess.}