Chicago 312: Your Boss Asked Claude If 312 Is Funny (I Hope It Said Yes)

Chicago 312 is a set of weekly field notes on Chicago power, written for people who live here.

What’s up! It’s spring! All mental illness in Chicago has been cured!

This week: after Midway Blitz the national news packed up, but ICE didn't. There are now two different Complete Streets projects with competing weekly rallies. Illinois has twelve days to tax the rich. And in tech, chatbots are the ultimate white collar scab.

Midway Blitz "Ended." The Deportations Didn't.

Block Club: On April 15, federal agents arrested Dario Quevedo Marquez, a Venezuelan asylum-seeker, as he left a South Side courthouse at 727 E. 111th St. after a hearing on a misdemeanor battery charge. His wife Daymelis Martinez asked, in Spanish, why they were taking him. An agent told her to be quiet or she'd be arrested too.

This is happening despite the Illinois Court Access, Safety, and Participation Act, which Pritzker signed in December specifically to ban federal civil arrests at state courthouses. Trump's DOJ sued over it the same month. Meanwhile, the Sun-Times got ICE to admit last week — in a letter seven months late to Sen. Durbin — that 81% of people arrested during Operation Midway Blitz had no criminal convictions.

And rapid response groups are seeing upticks in Belmont Cragin, Pilsen, and Cicero, where Organized Communities Against Deportations says pickups are back to daily.

Why It Matters: The spectacle phase of Midway Blitz is over, but what we're in now is the Obama-era quiet strategy: check-ins, court hearings, courthouse parking lots. It’s smaller numbers, but the same operation, and significantly harder to mobilize against, with nothing in the news cycle.

Get ICIRR's Family Support Network number in your phone: 855-435-7693.

Bike Lane Protests Are Now a Standing Weekly Appointment

Streetsblog: Every Monday, 4 to 6 p.m., a crowd gathers at Grand and Ogden to protest the Grand Avenue Complete Streets project. The project is already being built. It has won. But they are protesting anyway, every week.

Across the street, to make it interesting, there’s a weekly counter-protest. Monday's head count: nine pro, six anti. Meanwhile on Archer Avenue in Brighton Park, the same dueling weekly rallies have been running for 4.5 months. The cast is consistent: local merchants who believe their businesses die the moment a bike can reach them, a few suburban commuters with strong opinions about streets they don't live on, and Roger Romanelli of the Fulton Market Association — a lobbyist who has spent two decades killing Chicago transit projects as a professional career. Streetsblog's John Greenfield called him the Hillside Strangler of sustainable transportation.

Ald. Walter "Red" Burnett III (27th), who opposes the Grand project, reportedly told opponents there's nothing he can do to stop it — which is aldermanic for "I am not burning political capital on this one."

Why It Matters: Real talk — I am obsessed with this story and totally out of my depth on the internal politics of how this fits with all of the internal dynamics of NIMBYs, Brighton Park, bicyclists, etc. Someone should write about it. If that someone is you, hit reply. More ways to collaborate on Chicago 312 are coming soon.

Illinois Has 12 Days to Tax the Rich

City Bureau's Newswire: House Speaker Chris Welch is backing a 3% additional income tax on anyone earning over $1 million a year. Per a study from the Illinois Economic Policy Institute and U of I, it would raise $3.8 billion in year one, touch roughly 41,000 taxpayers, and leave the rest of us — 99.4% of the state — alone. Lawmakers have to pass a constitutional amendment by May 3 to get it on the November ballot.

Why It Matters: In 2020, Pritzker personally financed the Fair Tax (or the, “yes, tax the rich” campaign. In 2026, Pritzker — still a billionaire, now running for president — has gone quiet on taxing billionaires, which is a choice you can make when you are one. Welch is moving this without him. The millionaire-flight scare story is the same one that gets run every single time. Massachusetts passed a version of this in 2022 and the exodus did not happen. Mamdani is running the same play in New York. We know what works, tax the rich!

1 Big Question: Is Your Boss Making Claude Read This Email?

Rachel Karten writes the social-media strategy newsletter Link in Bio, and this week she asked her audience about working for bosses who have become AI-obsessed.

The specifics are more granular than the usual AI-takes-your-job coverage, but probably unsurprising to anyone with a terrible job. One highlight from the 200 stories: bosses are putting memes into Claude to check if they're funny before posting them.

In most of these cases, the human writer is still doing the work; the human is still the intelligence in the loop. What's changed is who gets trusted to judge the work. The manager has relocated their own editorial judgment to a chatbot. The chatbot's job is to produce something plausibly average — that's literally its design — and the manager's job has become delivering average-plausibility back to the team as feedback.

Karten cites a recent Stanford survey: 73% of AI experts think AI will positively change how people do their jobs. Only 23% of the general public agrees. And, as she says, duh: the experts are the people financially adjacent to AI.

This is happening in newsrooms, creative shops, strategy teams, and — increasingly — in government communications and political campaigns. It's going to shape what a lot of the work of 2026 and 2027 looks like, and more importantly, what it sounds like.

 🚨 "Tokenmaxxing" Is the Future of Terrible CEO Conversation

404 Media documented a new flex among startup CEOs: bragging about how much they spend on AI tokens. Swan AI's CEO posted on LinkedIn that his four-person company hit $113,000 in Claude bills in a single month and called it the proudest invoice of his life. Meta had an internal leaderboard called "Claudenomics" ranking employees by token usage before killing it.

OpenAI and Anthropic are losing enormous money on every query, the pricing is subsidized by investor capital, and nobody actually knows what these agents will cost when the subsidies end. 👍

🚨 The Onion Bought Infowars :)

Block Club: Some good news for once! Alex Jones is the Infowars guy who spent years claiming the Sandy Hook elementary school shooting was staged by crisis actors, got sued by the families of the murdered children, and lost.

Chicago’s own The Onion just reached a deal to license Infowars for $81,000/month (six months, renewable). The Sandy Hook families back the plan and get proceeds. hahahahahahahah

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