Maria Pappas Never Claimed to Be a Nun

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Maria Pappas has been the Cook County Treasurer since 1998. She's 76 years old. She signed with a talent agency last year as a professional senior model. She told Axios she became a model because she saw Elon Musk's mother modeling and thought, "I look better than her." She is an amateur baton twirler.

Every year she puts out a free calendar of herself posing in her collection of 60+ statement jackets — most of them bought at Akira in Block 37 — and you can pick up a copy at the store if you're fast enough (btw, if you're the type of person who would only go to the Akira in Block 37 to get a municipal calendar, they will know immediately).

She hosted a live radio show on WVON called "Black Houses Matter" about property tax overpayments in Black and brown communities. She figured out how to make people care about county government, which is something approximately zero other county treasurers have ever done.

All this happened BEFORE Pappas decided she wanted to be the Mayor of Chicago — since then, she’s started experimenting with Reels in a way that I can’t recap without derailing the entire piece.

In the past, even when I cringed, I had to admire Pappas' willingness to experiment and adapt, building a personal brand inside what is arguably the most boring office in county government. When progressive candidates spent thousands of dollars on weird videos in smoky rooms without mics or any hints about what their policy platforms might be, I looked on the Maria Pappas calendar with something resembling envy. Mostly confusion. But, I don’t know, there was envy too.

Chicago Characters in the Era of the Political Machine

There is a particular strain of Chicago political intensity that comes from understanding the stakes when everyone around you is trying to obscure them. It does not necessarily make you good at things, or fun to be around. But it does tend to make you a character, and Chicago loves a character. And Chicago has always produced characters like Maria Pappas.

Chicago used to have a machine. The machine was bad, a corrupt patronage operation that ate public resources and consolidated power in the hands of ward bosses, exacerbating segregation and empowering bad people. Bad people like Ed Burke, who held the same City Council seat for 54 years, ran a private property tax appeals firm out of the same office where he chaired the Finance Committee and got convicted on 13 federal charges. That machine is dead (good riddance), mostly. Though zombified traces linger on, particularly visible when trying to invoice anything in city government, it’s dead.

The machine used to absorb and deploy the energy of characters like Maria Pappas. It channeled people who were Like That into ward committeeman roles, patronage jobs, the kinds of positions where being a nightmare was actually useful.

Chicago Steak Knife Energy in the Era of Austerity

When the machine collapsed, privatization and austerity moved in. Austerity didn't require eccentricity, but it didn't mind it either. You could be completely unhinged as long as you delivered. Characters in Chicago Politics didn't disappear — in fact, many of them helped the privatization along (I wrote about this a few years ago in "Rahm Emanuel Steak Knife Energy," a great example of a Chicago character that thrived during the Neoliberal Era). And, while I don’t have any great jokes or new insights about Lori Lightfoot, it feels impossible to make this assertion without mentioning her here).

Chicago Characters in the Content Flywheel Era

Once the austerity deals dried up, a new Chicago politics era began, the content era. There's a whole infrastructure now that rewards characters: boring municipal policy decisions get picked up by conservative think tanks, amplified through Fox and the Daily Mail, repackaged on Reddit and TikTok as evidence that Chicago Is Dying, consumed by millions of people who will never set foot here.

Arguably, our current era is one of the best times to be a Character in Chicago Politics, though you have to freelance — Ja'Mal Green has run for mayor twice, gotten 2% of the vote, and endorsed Paul Vallas the day after Vallas's campaign paid him $28,460. Chicago Flips Red shows up to City Council meetings in "Take The Crook Out Of Cook County" hats, livestreaming to audiences of thousands without much of a policy platform beyond “hopefully we can monetize this,” and gaining shout outs from the ultimate final boss national grift level character, the president of the United States.

Pappas has been there for every one of these eras — the machine, the privatization, and now the content era.

Chicago Characters and Chicago Deals

This week, the Tyler CEO sent a letter to Pappas — copied to Preckwinkle and the county board — alleging she called a top company lawyer a "token Hispanic," used racial language about the county board president, threatened to destroy careers, and told a lawyer to "learn to speak English."

Cook County outsourced its property tax system to Tyler Technologies over a decade ago. Tyler spent that decade not finishing the job — tax bills went out months late, $8 billion in revenue to schools and local governments got held up, 80,000 taxpayers are still waiting on refunds.

Pappas says the "token" comment was actually a warning to the lawyer about how Tyler was treating her. She says, and I quote from the Trib: "I never claimed to be a nun."

Regretfully, like all Characters, Pappas says things that are very funny.

But, also like most Chicago Characters, she rarely has zingy one liners about her own suspect ties, including that she held stock in Tyler Technologies and other county contractors, and did not disclose this until the Tribune started asking questions two weeks ago.

Patronage was corrupt, but it was also a distribution system. Ward bosses were monsters, but they filled potholes because their power depended on it. Privatization, under the conceit of innovation, removed the distribution system entirely. It kept the extraction, but the ditched the part where anyone had to deliver anything to anyone.

Now characters in Chicago politics metabolize into content — calendars, City Council livestreams, merch drops, mayoral campaigns that go nowhere.

Maria Pappas is the best of them, and that's the problem.

Tyler Technologies gets paid regardless.