I've been MIA from this email list for the last couple of months, focused on various personal + existential + political crises.

One of the hardest parts of my life right now is learning to use Microsoft tools.

For people who have used Outlook for many years: how have you survived? What is wrong with you? What is your deal? Are you okay?

For example: WHAT IS THIS?

At any rate, today I'm back, ready to deliver your weekly-ish Chicago-specific-ish news clips. Let’s get into it.

Miscellaneous Headlines:

Acero Charter Schools Closing

Acero, a charter network once run by Juan Rangel (remember the former UNO head investigated by the SEC? Yeah, that guy), is planning to close seven schools. This move displaces over 2,000 students in Latino and low-income neighborhoods—another blow to community stability. Last week, CTU teachers and parents held a press conference opposing these closings. Today, as the new Board of Education is sworn in, organizers are calling on the CPS Board to investigate the largest school closings in Chicago’s Latine communities' history. 

This isn’t just about schools: it’s about who gets left behind when billionaires mess with education. Which ties well to… school board elections and the (11 Days Away) elections generally. And…

It’s Early Voting

Babe wake up there’s a new Girl I Guess Voting Guide.

This guide is the only election media content I’ve seen that talks about the history of the School Board, the role of a School Board in Chicago, actual power analysis, and the fact that “school choice” actually means “let private companies steal money from neighborhood schools and starve the system” Babe! Read it here: Girl I Guess Voting Guide.

Maria Pappas’ 2025 Calendar

Usually, when I ask Chicago reporters, organizers, or political agents about our city's Known Eccentrics, they’re eager to share their weirdest run-ins. Not so with Maria Pappas. “She releases a calendar full of glamour shots every year. H, I’m not sure what else there is to say?” said one political operative. Anyway, the 2025 Maria Pappas glamour shot calendar is out.

Random Television Thoughts

I think about Andor all the time. (Don’t you?)

Lately, I’ve been thinking specifically about when Cassian Andor finds himself imprisoned in the Narkina 5 labor facility, forced to labor under extreme conditions. The prison is a model of efficiency, rules, procedures, and enforcing compliance. The guards, the administrators, and the entire system operate smoothly, without friction or scandal, because everyone is “just following orders.”

Kino Loy, the de facto leader of the prisoners (played by a VERY jacked Andy Serkis, pictured above), is determined to play by the rules, hoping to eventually be freed.

As it becomes increasingly clear to Kino Loy that this system is fundamentally broken, unjust, and designed to strip people of their humanity, he realizes that the only way to break free is to get people to see beyond the technicalities of the rules and recognize the larger injustice (part of this is because of Cassian Andor organizing, which organizers love).

When Kino learns that no one is actually getting out, he realizes that despite following every rule and doing everything he was technically supposed to do, the system was always designed to exploit and imprison them forever.

How do you act differently when the “technically right” thing to do isn’t… actually the right thing to do?

I don’t have a good answer to this. It sounds easy, it’s very poetic, and in practice I feel like I fail at this 100000x a day, far more than I succeed.

But IMO, there could be a LOT more conversation about the responsibility to do things differently politically, even when it causes friction or scandal.

Especially when there’s a way (even a mandate) to challenge old power structures.

Anyway! I love TV, and fiction.

Shameless Community Promotion:

DMB’s Top Surgery Fund

Incredible reporter DMB Brown is raising money for his top surgery, and he’s raffling off some amazing tattoos to make it happen. Want to help him out? Donate here.

Loaves and Witches in the Chicago Reader

Loaves and Witches—my girlfriend’s bakery—was in the Chicago Reader this week! Am I biased? Absolutely. But also, they have killer pastries, cakes, and exceptionally good-looking owners. Check it out here.

Chicago Pride at Work Relaunch TONIGHT

Today at 5 PM, we’re relaunching the Chicago Chapter of Pride at Work! Pride at Work is about bridging labor rights with LGBTQIA+ rights. RSVP link is here.

Got an event, article, or anything you want to get out there? Send it my way.

Enough About All This… What’s your Halloween costume this year? I need ideas.

Otherwise, I’m going as a "tired guy who spends too much time thinking about Ray Lopez."

H

PS — I still work at the Chicago Teachers Union. Since CTU is the NeW POLItcal Machine, it feels like I should make sure you know that I write this at night, unaffiliated and unendorsed by my employer, way later than I should be awake, and aggressively not on the clock.