Beware of mayoral candidates from out of town
In Chicago, we have a phrase that means more than it sounds like it does.
“He’s not from around here.”
It’s not an insult, exactly. It’s a diagnosis.
What we mean is simple: Some people live in Chicago, but they don’t know Chicago. They weren’t born here. They weren’t raised here. They didn’t grow up watching how the city actually works — how power flows, how neighborhoods change, how crime rises and falls, how business and labor coexist, how politics is done when the stakes are real and the margins are thin.
Over the last 30 years, that distinction has mattered more than most people want to admit.
Chicago has long attracted people from elsewhere — especially from smaller Midwestern towns — drawn by white-collar jobs, big-city prestige, Cubs games on TV, and the promise of upward mobility. That’s fine. Cities grow by attracting talent. No argument there.
But when large numbers of newcomers begin reshaping the electorate — while long-time residents are getting mugged, taxed out, or simply worn down — the body politic starts to drift away from the lived experience of people who actually built the city.
And that drift has consequences.
The old check on naivete
For most of the 20th century, Chicago had a built-in corrective: mayors who were unmistakably from around here. The old machine didn’t just enforce loyalty — it enforced local knowledge.
If you look at Chicago's mayors from the 1950s through the early 2010s, a pattern emerges:
- Richard J. Daley — Bridgeport born and bred. Mayor until the day he died, literally at his desk. He understood the city because he was the city.
- Michael Bilandic — Another Bridgeport guy. Not charismatic, made mistakes, but they were pragmatic mistakes, not ideological experiments.
- Jane Byrne — Knew Chicago cold. Not a wild-eyed liberal, not detached from reality.
- Harold Washington — His family had been here for generations. He knew the terrain and governed with common sense.
- Richard M. Daley — Son of the mayor, raised in the system, fluent in Chicago’s language. His tenure—like his father’s—had flaws, but it was a period of growth, stability, and civic confidence.
- Rahm Emanuel — The Emanuel family had deep Chicago roots. Rahm was tough, transactional, and understood the necessity of working with business. As Democrats go, he was rational.
Notice something else: All of these mayors were Democrats. This isn’t a partisan argument. It’s a local knowledge argument.
When the wheels came off
The break came after the Laquan McDonald scandal, which cost Rahm his job. In the emotional aftermath, Chicago did what it increasingly does: It mistook moral signaling for competence.
Enter Lori Lightfoot.
Lightfoot was not from around here. She came to Chicago for a great job, became a successful lawyer, and climbed fast. But she never absorbed the city’s rhythms or instincts. The result was a string of decisions — no-chase policing, reflexive hostility toward law enforcement, open warfare with the City Council — that a lifelong Chicagoan would never make.
Then came Brandon Johnson.
Also not from around here. Elgin is not Chicago, and anyone who pretends otherwise is kidding themselves. Johnson doesn’t understand the city he governs. He doesn’t understand its finances. He doesn’t understand its business ecosystem. He doesn’t understand public safety. What he understands is grievance politics — race baiting, ideological signaling, and “Orange Man Bad” theatrics.
Chicago governance requires arithmetic. Brandon Johnson can’t — or won’t — do the math.
Every mayor who was from around here understood that business mattered, that public safety was non-negotiable, and that ideology always takes a back seat to keeping the city functional. Johnson governs as if Chicago were a graduate seminar.
It isn’t.
Testing the hypothesis
So here’s the hypothesis, tested against history:
- Mayors from around here tend to govern pragmatically, work with business, respect institutional constraints, and prioritize order.
- Mayors not from around here tend to govern ideologically, treat the city as a moral project, and underestimate the consequences of bad policy.
The pattern holds. Not perfectly — but clearly enough to matter.
What do we do with this?
First, we stop pretending this is impolite to say.
Second, we make “from around here” a litmus test — not the only one, but a serious one — when evaluating future mayoral and countywide candidates.
This doesn’t mean excluding outsiders by law or creed. It means recognizing that generational knowledge has value. Deep value.
Take Paul Vallas. Nearly elected. From around here. Deep roots. Sensible ideas grounded in lived experience. He understands how Chicago works because he’s watched it work — and fail — for decades.
The same standard should apply to county offices as well. How long has Toni Preckwinkle lived here? How deep are her roots? These questions matter more than the media likes to admit.
The harder problem: The electorate
Fixing candidates is easier than fixing voters.
Chicago has a diaspora — millions of people who grew up here, whose parents and grandparents grew up here, who still follow the city obsessively but moved to the suburbs for safety, schools, or sanity.
If Chicago could fix public safety and stabilize the economy, some of those people — or their children — might come back. That would be a good thing. But it’s hard. Really hard.
Until then, those of us who are from around here have an obligation.
We need to explain — patiently but firmly — what works in this city and what doesn’t. We have a historical data set that newcomers simply don’t have. We know why certain ideas fail, why others endure, and why Chicago is not like Davenport, Rockford, or Madison with taller buildings.
This used to be “the city that works.” It worked because people who understood it were running it.
That’s the argument. That’s the warning. And that’s what we’re trying to do here at Chicago Contrarian — pass along knowledge that took generations to acquire, before it’s lost entirely.
If you’re new here, listen up.
If you’re from around here, speak up.
Chicago depends on it.
