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

Here’s what matters this week —

3 Headlines:

1. City Council’s budget fight

WTTW: Chicago is staring down a government shutdown because 27 alders would rather hike garbage fees than touch a corporate head tax — and they’re gambling the entire $16.6B budget on casino revenue that doesn’t exist.

This is all to avoid reinstating a $33-per-worker head tax on the largest corporations operating in the city. Their proposal leans on airport slot machines that aren’t installed, “augmented reality” ads for the Riverwalk, and aggressive revenue assumptions city finance officials warn would jeopardize stability. Johnson says he’ll veto any plan that hikes costs; the bloc is daring him to try.

If this tax passed, Google, McDonald’s, and major financial institutions would pay less than the cost of an employee lunch. The head-tax scare campaign has no data behind it — studies show no link between modest employment taxes and job loss — but what absolutely does kill business climate is overflowing trash, fewer youth jobs, slower emergency response times, and cuts to public safety and mental health care.

Why It Matters: Inventing revenue that won’t materialize, shifting costs downward, and calling it “fiscal responsibility” is a weird way to build an alternative budget. If this faction wins, they set the precedent that corporate power gets protected and basic services get squeezed.

As the Black Voter Project and the Institute for the Public Good said on WBEZ this week: you can’t balance a $16.6B budget on wishful revenue and higher costs for working families.

2. Delivery Robots Are Taking Over Chicago

Block Club: Chicago’s sidewalks are being privatized one cute robot at a time. A fleet of delivery robots is rolling through Lakeview, Wrigleyville, and Northalsted with cutesy names, but residents are telling a different story: bots blocking crosswalks, stalling in snow, and piling up incident complaints. More than 1,500 neighbors have already signed a petition to “hit pause,” arguing the city never publicly debated this pilot, never assessed disability access, and never addressed who’s liable when a 450-pound cooler-on-wheels knocks someone down.

Why it Matters: “Innovation” is a great word for avoiding public oversight. These companies are using Chicago’s sidewalks as free infrastructure while creating new risks and undercutting workers. If the city doesn’t set boundaries now, it won’t get the chance later.

3. After a federal raid exposed unlivable conditions, South Shore tenants are the ones being forced out

South Side Weekly: Tenants at 7500 South Shore, whose building was raided by federal agents in September, are now ordered to vacate by December 12 after a judge declared the building unsafe. Residents say they’ve endured years of neglected repairs: no heat, broken elevators, flooding, mold, dead emergency systems, and 44 code violations this year alone. Now they’re being told to move in 16 days — during freezing weather — with relocation “suggestions” that don’t guarantee housing and a court-appointed receiver that won’t meet with the tenant union. Elderly and disabled tenants are effectively trapped in place, and the city has not intervened to delay the move-out. Organizers say: this is what happens when code enforcement, banks, and receivers get to quietly decide who deserves habitable housing and who gets shoved out of their neighborhood.

Why It Matters: It’s truly unreal that a building raided by federal agents could end with the tenants being the ones removed.

1 Big Question: Which Chicago survival strategy makes the most sense right now?

A) Tax Google $33/month
Because billion-dollar corporations are survivors!

B) Bet the municipal budget on imaginary slot machines
Bold choice. Innovative, even. Inspiring levels of delusion.

C) Let robots colonize the sidewalks and hope for the best
Disruption! Synergy! Liability concerns!

2 Red Flags Stressing Me Out Today: 

🚨 Can the Left Co-Govern?

The Forge: A write up from Oakland organizers show how co-governance works when it works: organizers using their skills on the inside, electeds expanding what’s possible, and movements staying aligned on strategy.

If organizers aren’t part of governing, someone else will be — and that “someone else” is usually the same old actors who know how to stall, dilute, or reverse hard-won gains.

🚨When Journalism Becomes Gambling

The Present Age: Kalshi, a prediction-market firm that openly says it wants to “financialize everything,” just scored a newsroom hookup national TV, turning betting on politics into part of the journalistic business plan. Their CEO also said the quiet part of their ultimate vision, and this particular economic moment, out loud at a Citadel Securities conference: “The long-term vision is to financialize everything and create a tradable asset out of any difference in opinion.” Beyond being one more death knell for the media industry and a creepy avenue for corporate actors to monetize public life, political betting at this level has disturbing implications as financial markets begin to act as governance.

Right now, Kalshi doesn’t need to follow state gambling laws. They get to call it “finance” and walk around the guardrails. Though states are starting to push back — media partnerships like this give Kalshi's ideal new normal credibility before regulators catch up.

That’s it.

If you ride a bike in this weather wear a helmet!

PS — Anti worker slander against Cats at Work