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

This week we’re focused on Chicago’s City Budget. I will never pretend to understand the city budget process fully, but let’s do our best. Starting with this quote from Alder Jason Ervin:

There’s also: people burning property-tax bills, humbling DoorDash, and the different ways political media gets paid.

The roundup is below:

3 Headlines:

1. Digging Into The City Budget

Johnson framed this year’s city budget as a simple choice: Tax the rich instead of property tax hikes, a grocery tax, or garbage fees. If City Council sends him a budget with any of those, he says he’ll veto it.

And as The Triibe reports, Mayor Brandon Johnson’s $16.6B 2026 budget hit a wall on Monday when the Finance Committee rejected his revenue plan 25–10, with the the proposed $21-per-employee corporate head tax on companies with 100+ workers at the center.

This budget also includes:

– A $1B TIF surplus — the biggest in city history with money towards CPS, Parks, Libraries, and City College,
– The SMART Tax — a challenge to Big Tech’s extraction
– A restored Department of Environment
– Shifting mental health funding from ARPA to the Corporate Fund —Easier to preserve in the long term,
– Efficiencies that include a hiring freeze, consolidation of real estate, and $200M in cost reductions without cutting resident-facing services,
– A new Community Safety Fund — the head tax revenue will support violence prevention, DV/GBV services, youth jobs, and mental health

The whole meeting, why it didn’t pass, and what happens next makes more sense if you understand some loose blocs that coalesced around this budget:

• Downtown/old school/anti-Mayor alders: (Conway, Reilly, Villegas, Scott, Coleman, Waguespack, Lee, Lopez), who say the head tax would hurt employers — without offering any real alternatives to fill the $1.15B budget gap. They were vehement, vocal, and had many, many procedural concerns, including being mad at Jason Lee.

• Progressives that support taxing big corporations but are worried about pension underpayments, borrowing to pay for police misconduct lawsuits, or another credit downgrade for the city. 

• The Mayor, most of the Progressive Caucus, and the People’s Unity Platform, leading the charge on taxing the rich. Good video here.

Meanwhile: Property tax bills dropped late, hitting South and West Side neighborhoods particularly hard. North Lawndale’s median bill nearly doubled; West Garfield Park shot up 130%; Englewood jumped 82%. People are so angry they’re burning their tax bills in a Boston Tea Party–style bonfire organized by the Lawndale Christian Development Corporation. Illinois relies on property taxes instead of taxing income or wealth, that lost revenue gets redistributed onto homeowners, especially on the South and West Sides where people rarely appeal in the neighborhoods with the least political power and the fewest legal resources are paying the highest increases. Cook County Treasurer, Aspiring Mayor, and Calendar Creator Maria Pappas says this is because downtown commercial buildings shed $129 million in value.

I bring this up only because so many in the first political bloc (and all of their X supporters) have pointed to exploding property taxes as proof the city has to “support business” by killing the head tax, a fractional amount to ask these giant corporations to pay. But there’s a deeper issue here: until Illinois can tax wealth, high incomes, or capital, there will be structural problems with Chicago’s budget.

Why It Matters: Chicago has a revenue problem made worse by commercial vacancies, state constitutional limits, and decades of underfunding public goods.

Chicago could have plugged a $1.1B hole the old way — by cutting youth jobs, raising property taxes again, closing clinics, gutting transit, and pretending “efficiencies” will save us. That’s what every mayor since Daley has done.

There’s a longer story about the pension payments, credit scores, what’s up with the assessor’s office, and all of the other pieces here.

But this is the first Chicago budget in decades that doesn’t balance itself on the backs of the people who already lost the most, and uses the city’s taxing authority where it exists.

2. DoorDash’s $18M Settlement

Axios Chicago: DoorDash just agreed to pay Chicago $18 million for hiding fees, listing restaurants without consent, and slapping a fake “Chicago Fee” on orders that looked like a city tax but went straight to DoorDash. The lawsuit, filed in 2021 at the height of the pandemic, forces DoorDash to:

• Pay millions to restaurants they listed without permission,

• Pay gig workers who got screwed by fees,

• Pay the city for the cost of dragging them into court,

• Admit that the “Chicago Fee” was fake.

And as WTTW reports, another lawsuit with GrubHub goes to trial on December 10th.

Why it Matters: DoorDash is a quietly influential municipal actor in cities around the country — but money isn’t everything when it comes to influence.

Back in 2023, DoorDash spread money across Chicago’s municipal elections, dropping $$ to incumbents sitting on the committees that kill delivery-app regulations or worker-protections. During the pandemic, they invented the fake “Chicago Fee” to make the city look like the villain when aldermen tried to regulate them.

But Chicago just successfully checked their power — it sets a strong precedent for pushing back on anti-regulation corporate lobbying.

3. Still No CEO For CHA

Sun Times: The Chicago Housing Authority has gone a full year without a permanent CEO, despite controlling $1 billion, housing 65,000+ households, and serving 5% of the entire city. The national search launched last year collapsed into a political standoff between Mayor Johnson and HUD over whether retired Ald. Walter Burnett could even be considered. HUD flagged conflicts of interest; Burnett and his wife have collected $260,000+ as CHA voucher landlords.

Meanwhile, internal instability has accelerated: eight senior officials have left in the past year — resignations, firings, and abrupt terminations with no explanation. Asset management, development, operations, and legal are all being run by interim leaders.

Dearborn Homes’ occupancy dropped from 95% to 88.7%, and one resident with a wheelchair was stranded so often he moved out, unable to get to appointments. Henry Horner Homes scored 26/100 on a HUD inspection, prompting a sudden change in property management.

The CHA board insists improvements are happening through a “year of renewal,” but most of those initiatives — a new environmental division, internal audit unit, reorganized property management — are being run by temporary leadership while the CEO seat remains empty.

Why it Matters: These problems are bigger than any one person: chronic understaffing, ancient buildings, federal rules that contradict each other, and decades of political interference from mayors, HUD, and the real estate industry. When you put all that together, you get a job no qualified person wants and no political coalition can agree on. So the agency drifts.

1 Big Question: Why Left-Leaning Media Can't Move Policy

Migrant Insider: As we’ve covered here repeatedly, conservative media build infrastructure — a network of think tanks, press access, billionaire-funded outlets, and policy shops that exist to move policy. Pablo Manríquez argues that, in contrast, left-leaning media keeps behaving like a VC startup, optimizing for growth, traffic, aesthetics, and brand partnerships instead of power.

So — even as progressive outlets rack up followers and produce solid reporting, they’re stuck in a reactive posture: responding to what the right already framed.

As always, a big part of the problem is funding. The right can treat media as a money pit because they don’t need clicks — they need influence. The left, meanwhile, has to pay its own bills, so our outlets chase engagement because that’s the only way to survive.

2 Red Flags Stressing Me Out Today: 

🚨 A Southern Socialist Win

Hamilton Nolan: Atlanta just elected Kelsea Bond, a 31-year-old labor organizer, to City Council, building a lane for democratic socialism out of support for Starbucks unions, the Nabisco strike, and transit fights. Great interview.

🚨 What is Queer Food?

Coyote: Not a red flag, but I’m excited about Coyote, a worker-owned Bay Area media collective mixing culture, politics, and community reporting. I want to see more independent culture reporting, and ’m a long time Soleil Ho + Daniel Lavery fan! If you haven’t subscribed, IMO this piece is the one to do it for, exploring what ‘queer food’ is, how queer is used as both buzzword + useful community marker, and important questions like “What are you about? What did you mean by that? Why did you touch my shirt?”

Finally…

Earlier this week I wrote about why organizers should make vertical video. Check it out.