To most outsiders, Chicago is perceived as the home of a monolithic Democratic Machine.
That's not quite true. While Chicago and its inner suburbs churn out votes in a classic political machine-like fashion, there are really two machines.
Greek mythology provides a parallel, Orthrus, the two-headed dog.
As for Chicago's two-headed dog, it consists of the Cook County Regular Democratic Organization, headed by Chairman Toni Preckwinkle, who also serves as president of the Cook County Board of Commissioners. That’s the Preckwinkle Machine.
The other head of the beast is the Chicago Teachers Union Machine, led by president Stacy Davis Gates. A screaming harridan, Davis Gates is referred to as “the Notorious SDG” by Chicago Contrarian's George Shay.
For now, both Preckwinkle and Davis Gates are allies. However, as Charles De Gaulle said of international relations: “No nation has friends, only mutual interests.”
Chicago area moderates and conservatives want both heads of the Machine dog to be defeated. So, it's a two-front war. Both must be crushed, but to do so, common-sense voters need to know how they operate.
Preckwinkle
The Preckwinkle Machine is Boss Toni Preckwinkle. Because Cook County government, compared to that of the state of Illinois or of Chicago, exists mostly in the background, she receives little blame when things wrong.
And do things ever go wrong in Cook County.
Contrarian's Paul Vallas has been leading the charge in attacking Preckwinkle the public servant.
Earlier this month on X, the longtime civil servant let loose on her:
“As Cook County Board President Toni Preckwinkle rolls out her $10 billion 2026 election-year budget trumpeting her ‘fiscal management,’ voters are best reminded that the budget has more than tripled during her tenure and public safety’s share has plummeted from 41 percent to 18 percent."
Most disappointing is the absence of any meaningful property tax reform during her tenure, as property taxes have jumped 78 percent since 2008 — more than 10-times the 7 percent increase in home values. In South Suburban communities, property taxes soared a whopping 20 percent this year.
Among her wasteful spending is $265 million frittered away through the hire of politically connected Tyler Technologies to fix the broken property tax system. The result of this debacle is delayed property tax bills and disbursements to taxing districts, forcing them to borrow to cover payments.”
Longtime lobbyist and City Club of Chicago president Jay Doherty, now a federal inmate, assisted Tyler Technologies in winning County work.
Preckwinkle’s cozy position in the background vanished in 2017 when she championed the deeply unpopular county soda tax. The Cook County Board surprisingly rebelled and one of the leaders in that battle was fellow Democrat Richard Boykin, a commissioner who represented a district on Chicago’s West Side.
Boss Preckwinkle lashed out.
In the following year’s Democratic primary, the Two-Headed Machine endorsed pro-Chicago Teachers Union candidate Brandon Johnson, an unknown CTU organizer.
On the October 4 episode of the Chicago Contrarian podcast, radio host Amy Jacobson explained what happened next.
“Brandon Johnson won, but that’s how we got Brandon Johnson. He became a Cook County Commissioner; and then became the mayor. So, she’s Tony Preckwinkle again — and is pulling all the strings.”
Kim Foxx, a former Cook County assistant state’s attorney, was another unknown. Prior to her two ruinous terms as State's Attorney, Foxx served as chief of staff for Preckwinkle. Pulling strings, Preckwinkle managed to place Foxx in office, where she ran a pro-criminal, catch-and-release operation as the county’s chief prosecutor — or better yet, sort-of prosecutor. Foxx made her wisest decision in office when she decided against seeking a third term in 2024. Preckwinkle and her Machine, as well as the CTU, lined up behind another unknown to succeed her, Clayton Harris III, who vowed to continue Foxx destructive policies.
Fortunately, Harris' opponent, Eileen O’Neill Burke, with the help of a few Republican crossover voters, won a narrow victory in last year’s Democratic primary. She’s now cleaning up the public safety debacle created by Foxx and Preckwinkle.
The Chicago Teachers Union
The CTU’s level of failure is similar to Preckwinkle's.
According to the most recent third-through-eighth grade reading scores, fewer than one-third of Chicago Public Schools students read at grade-level. Mathematics is even worse: Less than 18 percent of CPS students score at grade-level. High school test scores are terrible too.
The old CTU argument of “But we’re the union, not the management” is as strong as a wet potato chip. The CTU is a generous campaign contributor to key legislators in Springfield and in the City Council. And of course, for the last two years, their former organizer, Johnson, has been mayor.
The current Chicago Board of Education is a hybrid model, ten of its members are elected, but despite spending $2 million on those races last year, only four of its candidates won. The other 11 seats are held by Johnson appointees. But that adds up to 15 of 21 seats being Johnson/CTU controlled.
Preckwinkle can’t govern. The CTU can’t educate.
Since neither head of the Orthrus dog can run on their records, their message is simply: Republicans are evil and Trump is worse, and oh yeah, white supremacy is everywhere. And don’t forget the patriarchy.
How to defeat them
As for Preckwinkle, weakening her machine is as simple as defeating her in next year’s Democratic primary. She is running for reelection as Cook County Board president.
Fortunately, moderate and conservative Cook County voters have a solid choice in Brendan Reilly, the alderman of Chicago’s 42nd Ward.
Reilly pummeled Preckwinkle last month on the Fran Spielman Show podcast.
“The far left that has been ushered into office under Toni Preckwinkle’s leadership has been conducting lots of social experiments that … are very expensive. They’re hard for us to afford, and we’re not even sure if there’s any kind of return on investment.”
Reilly went on to slam her for being the schemer who put Kim Foxx into office.
Next steps
It won't be easy, and remember, O'Neill Burke only bested Harris by only 1,500 votes, but voting Preckwinkle out next year will likely lead to her resignation as party leader, because when her term ends, she won’t directly or indirectly control any government jobs. Her political doppelganger is another current federal inmate, Michael Madigan. His quick resignation as chairman of the Illinois Democratic Party followed his defeat for another term as state House speaker.
Even with Stacy Davis Gates, “the Notorious SDG,” at the helm of the CTU, its power is more dispersed, like swarms of mosquitoes at a picnic. But the union can be defeated too.
Do some research before voting next year. Unless they are unopposed, vote for the opponents of the candidates who are endorsed and funded by the CTU. That will be extremely important next year because every seat on the Chicago Board of Education will be decided by voters in the November general election. And it's a safe guess the CTU views Johnson as a gone goose in 2027. They’ll see board elections as their political redoubt.
And there is always the possibility — wouldn’t that be great? — the two heads of Orthrus the Dog will turn on each other as they are attacked from the outside. Remember De Gaulle’s observation about international relations.
And yes, we live in a dog-eat-dog world.
One more piece of advice, as Green Day sings:
“Do you know the enemy?
Do you know your enemy?
Well, gotta know the enemy, rah-eh.”
You know what to do. Rah-eh!
