Welcome to Chicago 312: 3 Headlines. 1 Big Question. 2 Red Flags. Every Wednesday (…except for these last two weeks). Subscribe here.

Trump’s deportation blitz keeps mutating; City Hall gives a LOT of money to companies working with the current ICE crew (it doesn’t have to be like this), six Chicago organizers + politicians got indicted for existing; and Springfield’s transit plan died mid-sentence while Pritzker explained that “more work needs to be done.”

Let’s get into it! only 17 hours later than usual!

3 Headlines:

1. Where in the World Is Greg Bovino?

Reuters: Judge Sara Ellis made the Border Patrol commander known for the world’s weirdest thirst traps and bad hair report to her courtroom after video showed him throwing a tear-gas canister at protesters—and at kids walking to a Halloween parade in Old Irving Park. She mandated he had to clock out of his raids and clock in with her at 6 PM every day — he also admitted under oath he didn’t have a body camera. “Ninety-nine percent of my agents do” — Ellis told him to buy one, or to pull strings with Kristi Noem to get one. But then the Justice Department appealed, and now Bovino’s bench check-ins are suspended, so this particular piece of political theater may have just… strengthened the federal and legal mandate for the scaled terrorism happening across the city.

In other bad federal news, Kat Abughazaleh, Cat Sharp, and four others still face federal charges for “impeding an officer” after a September protest at the ICE facility. In spite of the fact that ‘the Broadview Six’ is such a cool name, this is still a ludicrous move from the feds. Trials start next month.

Why It Matters: I put these two together because the breaking news immediate appeal of ANY real mandate for Bovino to be accountable to this federal judge not only threw me enough to delay the newsletter (my bad), but is in real contrast with the government deciding to prosecute Chicagoans for standing in front of vans. When the feds are the aggressors, “accountability” becomes theater; when Chicagoans resist, it becomes conspiracy — not surprising but definitely showing the increasing limits of court power without political will behind it….

2. Chicago Can’t Fund the Companies Funding ICE…

Sun Times: Based on reporting from Manny Ramos at Block Club) Ald. Rossana Rodríguez Sánchez is calling for a review to stop funding companies that arm the same agents terrorizing Chicago residents, including Motorola Solutions—$267K Homeland Security radio deal, $87.9 million in city contracts, SP Plus—$206 million to manage O’Hare parking; also leases spaces to ICE in California, Invisio Communications—makes tactical headsets for HSI and got $31K from the city this year, and CDW Government—forensic computers for ICE and a $10.5 million city tech contract.

Why It Matters: Somewhere in the basement of City Hall, there’s an office where people with spreadsheets decide which companies get hundreds of millions in public money — and that’s where power actually hides. What would it take, if the city can’t (or won’t) block ICE outright, to starve this ecosystem: ban vendors who equip raids, redirect contracts, and use “responsible bidder” clauses as political weapons? This is an opportunity for the municipal government to work on new creative ways to quietly pull levers — by deciding who gets paid.

3. The Transit Cliff Is Still Coming

CBS: House Democrats in Springfield unveiled a plan to raise $1 billion for CTA, Metra, and Pace: 7% entertainment tax, 5% “billionaire tax” on investment gains, and half the revenue from speed cameras. CTA driver Tiffany Rebb called it what it is — a fight for her job. Gov. JB Pritzker immediately said the plan’s “not going forward.” Unclear what will go forward, at least in time to keep Chicago’s transit system surviving.

Why it matters: Pritzker wants a “world-class transit system,” just not this one… or one that’s funded… I guess. Cuts of 25% start next summer if nothing passes. When politicians say they need “more time,” what they mean is they won’t be the ones waiting for the bus.

Two bonus stories: a measured review of the city budget and a great piece from my favorite critic of the Left (including the fact that none of us know what “the Left” even means) — Yasmin Nair on whether the Left is addicted to crisis.

1 Big Question: What’s Your Favorite Neighborhood for Time Travel in Chicago?

2 Red Flags Stressing Me Out Today: 

1. Biden’s Former Press Secretary Is Loyal If Nothing Else

   The New Yorker: Isaac Chotiner’s New Yorker interview with Biden’s ex-press secretary should be in a Museum. She says she left the Democratic Party because they were “mean” to Biden. No mention of Gaza, war, or policy — but the words “wait, wait, no,” show up a lot.

   Why it matters: There are not a lot of reporters that… ask questions in the national landscape right now, and it’s bad enough that the Pentagon is banning access for national outlets. Obviously Jean-Pierre is not part of that regime, but it seems like this unwillingness to press interviewees extends even into convos about book deals. TLDR — I just enjoyed this.

2.  The >30 Person Trump Revolution in Chicago

   Silly Prizes: Friend of the newsletter Bebo launched SILLY PRIZES, a city hall blog, with a deep dive into the ChicagoRED PAC—the Trump-aligned “Black Ladies in Red Hats” crew that heckles City Council (and also me in my replies but that’s not as newsworthy). Highlights include: only 34 donors from Chicago and uh, having accidentally doxxed their own donors by hand-itemizing small gifts.

   
   Why it matters: The right’s offline ecosystem is loud and its grift still sucks up oxygen that should go to real organizing. Also: read Bebo. He’s funny.

PS — After last week I had SEVEN people reach out to get connected with rapid response + community support groups in their area. It was awesome.

For individuals or volunteer groups, I’m always around for support, troubleshooting, promo, brainstorming around how you personally can get involved in city politics, mutual aid, or trolling the Right on X.

End the week doing something useful instead of doomscrolling:
Join the Little Village Community Council for an ICE Watch during the neighborhood’s Halloween parade — volunteers will walk with kids and families to keep them safe as they trick-or-treat. 4–7 p.m. Friday, Oct. 31, starting at the Little Village Arch (26th & Troy). Register here: luma.com/ze5flyuh.