Welcome back. For better or worse, we are less than 6 months out from the municipal elections (and only a few months away from Chicago’s first ever fully elected school board election). Are you ready? I’m not!*

This week: who gets to explain CPS, twelve alders swore off ICE money, and "surround sound" communications in organizing.

1. Defining the Stakes of the School Board Race

There's a new book by David Backer, As Public as Possible (NPQ interview), that says every school district is defined by one of two stories in this post-Trump, post-McMahon funding deficit era.

Story One: it’s all the fault of the individual district, with no fiscal responsibility (or, more moderately, that any funding crisis means there’s nothing to be done — other than cuts, closures, and laying off as many people as possible.

Story Two: Actual attempts to explain what’s happening in education policy with nuance —state underfunding, the end of federal programs, and lenders collecting interest on the delay.

Last week was the launch of the "CPS Excellence Agenda" from Austin Berg's The Last Ward, part of the Koch funded Illinois Policy Institute cinematic universe, and Berg's platform is narratively laundering support for story one, including l cuts and ‘fiscal responsibility.” He argues to set a "minimum standard" for enrollment, faster charter renewals, a rewrite of state law to weaken unions at the bargaining table, and fines for school board members who step out of line.

Why It Matters: On November 3 whoever wins the explanation wins the right to decide what happens next for CPS.

And, there’s another way to run, beyond just hyping up the needs for cuts. In contrast, School Board Candidate (and former CTU staff) Hilario Dominguez is campaigning on free, full-day pre-K starting at age 3, built through the home and community providers CPS already relies on. I’m highlighting this year because I’m not only as these school board election being undercover, but I think most conversations about this election included a very few discussions of real meaningful changes that could be made through CPS.

2. Twelve Alders Just Swore Off ICE Money

Tribune: Twelve Progressive Caucus members signed the "ICE Out of Chicago Elections" pledge Monday, saying they would take no campaign money from companies tied to immigration enforcement. The list includes Motorola Solutions, Amazon, Microsoft, Home Depot, Target, and the Illinois Hotel & Motel PAC. This comes from the coalition behind the Chicago Fair Elections Ordinance — ICIRR, The People's Lobby, Reform for Illinois, and others.

Why It Matters: After Midway Blitz, everyone in Chicago politics says they're against ICE — but this pledge is a step towards actually making that claim mean something material.

3. Chicago’s Pension "Crisis" And Why It Matters

Conor Durkin recently wrote a 2026 pension update at A City That Works — it’s worth reading, at the very least so we can fight in the comments.

Chicago's funds are 28.1% funded, about $36 billion short, and three straight years of better-than-11% market returns dragged the funded ratio from just 25% to 28%. This isn't a normal municipal finance struggle, to be clear; the national average is around 82%.

For decades, Chicago funded pensions by paying in less than it needed, every single year.

But like all revenue options, Chicago's tax menu is deliberately narrow: the state won't let the city tax income, so the "easy" levers for budget money are the most regressive ones, landing hardest on the people least able to absorb them (think: fees and fines).

So, without popular political options to fund these pensions, the problem has just been sitting there.

This means during every budget season, Chicago is in a pinch — this giant pot of money needs to be paid into, but the surface level solution is to pit paying pensions against funding real government services like the bus running on time.

Why It Matters: I am just some guy, at the end of the day, neither a credentialed municipal finance expert nor even the type of person who gets excited to argue about Chicago’s credit rating online (there’s a reason I’m off X, beyond the virulent… X stuff happening on there).

But after many years of trying to wrap my head around this, I still believe that it doesn’t have to be like this.

Recently, New Jersey (#2 in the country re: pension payment issues) made its first full pension payment in twenty-five years, and paid for it partly with a millionaires tax — accomplished in part because a lame duck Governor was willing to take the political hit.

Ways to change the overall revenue issue that tax the rich require much more organizing: Springfield's graduated income tax died at the ballot in 2020, and a financial-transaction tax on the LaSalle Street exchanges — where trillions move through this city — has sat on the shelf for years.

But Chicago is not broke. Chicago is a city with enormous wealth and a government that's only allowed to bill the people who have the least.

1 Big Question: How to Build a ‘Surround Sound’ Communications System

Ritti Singh wrote "Surround Sound Communications: How to Build a Narrative Machine" for Convergence this spring, who ran communications for Housing Justice for All and the New York Tenant Bloc — making "Good Cause Eviction" the largest expansion of tenant rights New York had seen in fifty years, and turning "Freeze the Rent" from a bumper sticker into a line that helped pick a mayor. She's now deputy comms director on Claire Valdez's congressional campaign.

We got into what "surround sound" actually takes when it comes to saying the one true thing over and over until it sticks. An excerpt from our conversation, lightly edited (mostly removing me saying “WOW!! YES!”):

H: If you were going to summarize what you’ve shared about organizing communications here, what would you say?

Ritti: One thing I'd like people to take away is simply that communications work is organizing. The way I sometimes talk about it: comms is how we have an organizing conversation at scale. I started as a building organizer in the tenant movement, which means you're getting the issues, laying the blame, giving a plan to win, making a call to action. And those are also the components of really good messaging. What you're trying to do is invite people into the movement. Sometimes you do that at someone's door, sometimes on a phone call, sometimes in the parking lot outside your workplace, but you can also use press and social media — every avenue where people are talking to each other. All of that is organizing. What we're actually trying to do is bring tens of thousands, hundreds of thousands, millions of people into our shared story: why our lives are hard, who's responsible, and what we can do about it.

H: One thing that really spoke to me in your article that I don't always see people talking about, let alone talk about at a scale that will work for organizing groups, is the focus on distribution.

Ritti: When I started doing comms — going from New York's eviction moratorium expiring into the fight for Good Cause eviction protections, which we fought for three very hard years and won — I was doing what I was taught to do. You find a really good tenant story, somebody who fought an eviction or faced a horrible scummy landlord, and you get maybe one press hit. I remember a big New York Daily News cover, and you go, 'we did it,' and move on. Someone I worked with said, oh, maybe years ago that cover would have worked, and everybody would have seen it. But that's just not true anymore.

H: How do you think about your strategy in contrast to the right, and how they approach this, putting a lot of money and resources into communications?

Ritti: A core belief of mine from tenant organizing: sometimes tenants would start spouting anti-immigrant stuff — 'my housing's expensive because immigrants are taking it all up' — and everyone would freak out: 'we lost.' But the same exact people are saying 'I hate my landlord, he keeps raising my rent.' Both things live in the same person. The question is just: are we present and visible in their lives? We don't need a billion-dollar commercial media apparatus. If trust in institutional media is low, stepping into that vacuum through relationships, trust, and organizations gives us an edge.

I’ll send this full (great) interview out in the next week as a standalone, part of 312’s expansion. Please check out the training, hosted by Convergence, later this month.

2 Red Flags:

🚨 People Really Hate Data Centers, Water is Wet

Politico: 63% of voters want to pause AI data-center construction — 67% of Democrats, 66% of independents, 58% of Republicans. There is almost nothing else in American politics we can all agree on (besides, like we talked about last week, how it’s too expensive to live).

🚨 Do We Really Need a "Charlie Kirk” for the Left in 2026, Oh MY God

Excuse the clickbait-y title and check out Grace Weinstein’s piece at Who Broke It on Zee Cohen-Sanchez's "Unfuck America Tour". I felt like this was a good overview of where the whole ‘the Left has a narrative problem’ conversation has landed nationally after a year of hot takes (in contrast with say, actually meeting people where they’re at like we talk about in the interview above).

That’s It This Week!

In case you were wondering, I still don’t know how I feel about the Odyssey movie.

Maybe we can all read Emily Wilson’s Odyssey to prepare for the Mayor’s Race?

See you soon,

-H

*If you feel the same way I do, read Megan Thuy and Steve Tapas's mayoral field guide at The People's Media Project — a great opener on where this race is heading.

A (Bonus) Question About Money, Part Two

The 312 Reader Census is seven questions, takes three minutes, and shapes what this newsletter becomes. Fill it out and get entered into a giveaway for a $75 Loaves and Witches gift card (I bought it outright, don’t send them hate mail about the pensions).

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