Guest Column–Matt Rosenberg: It’s “Office Time” For Chicago: Let’s Spitball The City’s Future

By Matt Rosenberg


When I drove a Yellow Cab in Chicago in the late 70s, I learned to love donuts. Because in true Chicago form I used them for bribes. If you wanted the mechanics in the old garage on Halsted north of Belmont to fix something on your cab, you needed to come bearing a dozen, the Chicago Way.

Now – as Chicago’s Black middle and working classes continue to flee for places with less shooting and killing, lower taxes and fees, less costly regulations for entrepreneurs, and better K-12 schools – our city increasingly looks like a donut. Albeit one irregularly gnawed from the inside out. As if by crafty rats. 

We’ve arrived at what Chicago’s flailing Mayor Lori Lightfoot calls “office time.” Let’s do some blue-sky brainstorming. And spitball the future. 

Wild West streets are but one of a crippling series of institutional failures in the city that no longer works. So try this: a city contract with the electorate that’s also a competence manual. A modern-day city charter could be a city constitution and road-map for better governance. Other cities do this. We’re overdue. 

If voters bite on a related ballot measure which could materialize in 2023, it starts with a charter commission. No current or former office-holders allowed. Then the new charter is drafted. It and subsequent revisions go to voters. In Illinois, a Chicago city charter might or might not require sign-off from the legislature. If it does, fine. Force the issue. We’re already in the late innings and the other side has run up the score.

Yes, proxies of vested interests would seek to control a Chicago city charter to protect their carve-outs from encroachment by the greater good. Yet just maybe the threat of public employee unions off-stage but still writing the city’s new rule book, is just what apathetic citizens need to know about. So that they finally get off their rear-ends. 

A city charter for Chicago is probed in an important and deeply-researched 2019 book “The New Chicago Way,” co-authored by Ed Bachrach. He’s a retired retail clothing company CEO, and a CPA who also earned a master’s degree from Harvard in public administration. His co-author was Austin Berg of the Illinois Policy Institute. Take a deep breath here. They’ve been known to consort with…Republicans!

Bachrach and Berg stress that a city charter could ensure the professional rather than politicized management of Chicago’s police, schools, legal affairs, personnel, and especially finances. One crucial innovation would be a full-throated legislative fiscal analyst, to keep spending decisions honest, as does the Congressional Budget Office for the federal government. Bachrach and Berg also argue a city charter could importantly reclaim for the city council certain powers given away to the mayor. Like running council meetings, and deciding and appointing council committees. 

A city charter could institute badly-needed two-term limits on council members and the mayor. It could even shrink and reform our 50-member city council, where insider gerrymandering means politicians pick their voters, not vice-versa, and corruption is endemic. Experts say that generally, only ten percent of public-sector grifters are detected. Do the math: 3 of Chicago’s 50 aldermen are currently indicted. True, the council has a few stellar members, and most could be ineffectual or spineless, rather than criminal. 

Still, Chicago’s finances are a flaming, cartwheeling train wreck. Bachrach and Berg crunched the city’s pension plan numbers and saw about $170 billion (yes, with a “b”) in public employee pension obligations for Chicago taxpayers, to 2055. A dramatic reckoning is due and a charter could help, by requiring referendums for all city tax hikes and future borrowing. 

It could mandate an elected city comptroller and city attorney, and a professional police commission – not a mayoral appointee- running that crucial department. It could also ensure a stronger role for citizen advisory committees. 

A new city charter could affirm much fuller electoral participation as a guiding value. So that officials could be pressed to win from state legislators approval for Chicago elections held on presidential election dates, when city turnout is 70 percent. 

This in contrast to the current Wise Guy scheme: an odd-year, early-months city elections schedule that assures scant participation, of just one-third of Chicago’s registered voters. 

A city charter might even formalize intent to push in Springfield and federal courts for full-on K-12 school vouchers for Chicago families with children. Remember children? This is a school system in which less than one-fifth of Black fourth and eighth-graders can reach the lower “proficient” bar in reading and math on the National Assessment of Educational Progress.

Still, despite the obvious benefits, I can hear the guffaws about a city charter for Chicago. When has doing the right thing ever mattered? But here’s what world-weary detachment gets you. In 2019, the number of Democratic Socialists of America members on the “non-partisan” Chicago City Council grew from one to six. There’s more of that to come, if Chicagoans sit idly by. The Bernie Bro cadre didn’t birth Chicago’s decline, but they’ll surely keep advancing it.

What of the Terror Dome the city has become? Chicago’s head of police reform did manage to hint at the consistent foot patrols so badly needed in high-crime areas.  But the Tribune parsed his words this way: “That could mean efforts like getting out of patrol cars and walking through neighborhoods on foot.” Could mean? Good Christ! Must everything be a tippy-toed trial balloon in this city of fear? 

It seems as if the real worry is not actually Chicago’s endless river of blood, or its rain of bullets. Instead, the bugaboo with foot patrols is that some race hustler is poised to yell, “Over-policing! Systemic racism.” All the more reason for drafters and voters to carve professional, not political management of the police department – into their approval of a city charter’s assorted provisions.

News reporters close grim segments on the latest looting and armed robbery sprees, carjacking waves, rolling shoot-outs, and mass killings with rote, furrowed-brow reminders to beware of your surroundings and call police if you see anything suspicious. They might as well add, look both ways before crossing the street. And wash your hands when you get home.

I smell something deeply rotten. It’s the silence – one bout of throwaway mayoral remarks aside – about parents that won’t parent. Schools that won’t teach. Leaders who won’t lead.

And citizens who won’t use their rights to better shape the fate and future of our people’s republic, right here in this city at the end of its rope. It’s this silence that is violence. 

Without a viable Chicago, Chicagloand cannot hold, over the long term. 

Unless Chicago breaks out of its rut, Chicagoland will become a donut chewed up from the inside out.


Matt Rosenberg is the author of What Next, Chicago? Notes of a Pissed-Off Native Son.” He also writes at ChicagoSkooled. He lived in Chicago for 30 years, and returns frequently. He has worked in media, public policy, and communications since serving on the undercover team of the Mirage Tavern investigation in 1977. Reach him at

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