
A couple notes up top:
First, a new event on October 8th: Let’s get to work: A pro-housing agenda for Chicago: Join Aldermen Red Burnett, Gil Villegas, the Mid-America Carpenters Regional Council, and A City That Works to talk housing, development, and organized labor. We’ll be at Everything Bar from 5:30-7:30pm. Register here.
Second - we’ve had a lot of new subscribers this year. Welcome! We’d love it if you’d take a couple minutes to fill out our reader survey, which is really helpful in giving us a sense for where this project ought to go and what we should be doing more/less of. Thanks!
Back in July, we put out a call for questions for our inaugural mailbag post. Then we promptly forgot to respond. Sorry about that! Here’s some overdue responses to a few of your questions.
Tex Pasley: Should the city be more proactive about encouraging commercial business growth (whether through better zoning, reducing regulations, etc.)? While certain commercial corridors do very well, the average neighborhood has a depressing amount of vacant commercial storefronts.
Almost certainly, although we haven’t gone deep on this issue (yet). Broadly speaking, it’d be great to see tweaks to make it possible to rent smaller amounts of storefront square footage, and lower the burden to open. It was also really nice to see Alderman Yancy’s resolution for a Small Business Bill of Rights - but it’d be a lot nicer to see the rhetoric in that resolution followed by some real action on behalf of the city.
As one specific, it seems like this is a particularly pronounced problem for daycares - which can be great neighborhood assets and tenants (and seem to make particularly good first-floor commercial options below a residential building), but often have to spend a long time in permitting and approval purgatory before they can get up and running. But if you happen to know more here, drop some thoughts in the comments or shoot us a note.
John Crowley: You’ve written about the importance of economic growth for Chicago & flagged various policies as anti-growth, but how would you assess Chicago’s overall climate for economic growth? Where are our biggest opportunities & biggest road blocks?
It’s not great. The best evidence for that is the fact that Chicago’s growth rate has lagged the rest of the country by quite a lot over the last few years. We have some real strengths: we’re a city with a highly educated workforce, a diversified corporate sector, and a lower cost of living than most of the coastal markets that we often think of ourselves competing against. But those strengths haven’t been enough to foster a robust tech ecosystem, and we lose the tax and cost of living battle to the fast-growing cities of the South.
Some of this is outside of the public sector’s control: there are idiosyncratic reasons that the tech boom occurred out in the Bay Area, and people really hate cold winters. We’ll spend more time on this in the coming months, but the biggest opportunity to spur growth probably mostly revolves around getting the basics right, including better public safety, and handling city finances. The challenge is that the sorts of taxes that are most damaging to future growth (like the tax on cloud computing) are often the most politically convenient levers to pull. On the other hand, those seem like easier problems than, say, places like Phoenix figuring out water shortages and 110 degree summers (or even New York City solving their housing crisis).
ben: If you were in charge of CPS, how would you go about starting to solve their structural deficit issues?
There’s been a massive decline in the number of kids attending CPS, and it’s likely to continue. Most of that is just because there are far fewer children living in the City of Chicago. That’s really hard, but it also means there’s a real opportunity here: declining student numbers plus a relatively robust tax base could allow you to invest more in each student in the coming years, while slowly crawling out of the district’s fiscal hole and paying down debt.
But that only works if you address the fixed costs. Chalkbeat’s piece last summer about empty schools made a pretty powerful case for how bad it is *for students* that we have so many underutilized schools, and the only way to change that is to right-size the number. Ideally, you’d have a long-term plan for how school buildings are used that includes a real community input, and a transparent selection criteria for consolidation, renovation, and new school construction. That’s very different from attempting a one-off school closure push a la Rahm, OR from pretending this issue never has to be addressed.
Also, the State of Illinois should handle CPS pensions the same way it handles every other District in the state. It’s basic parity and would make a huge difference for the District.
John: What do you think of the all-pedestrian crossing coming to the Six Corner intersection in Wicker Park?
We’re not traffic engineers, but it sure seems like a good idea. One of the issues right now is that cars come whipping around North Avenue trying to make right turns into multiple layers of pedestrians. Giving pedestrians a real chance to clear out in multiple directions might reduce the amount of pedestrian-driver conflicts, which would be a good idea. It’d also be nice if the city actually enforced the ‘no left turn’ restrictions northbound on Milwaukee (for similar reasons).
John: What are the biggest successes of the Johnson administration?
The tongue-in-cheek answer is that for fans of good governance, they’ve done a remarkably good job inducing City Council to serve as an independent, coequal branch of municipal governance, rather than just a rubber stamp for the mayor. Council has become a lot more assertive over this term, and that’s not likely to change in future years regardless of who wins the 2027 mayoral election.
The actual answer is probably a few of the top personnel selections. Department of Planning and Development Commissioner Ciere Boatright seems to have been a good pick. She’s gotten a number of big projects moving (including Foundry Park the 1901 Project), and generally seems to be well regarded. It also looks like Aviation Commissioner Michael McMurry has managed to speed up construction on new gates at O’Hare Airport, which would be a real win for the city’s long-term health. Larry Snelling was also a solid pick - and while it’s true that the Mayor’s record on public safety deserves to be assessed against other cities, it’s also true that if murders were going up everywhere he’d be getting blamed (just ask Lori Lightfoot). At a minimum, this is a case where the doom and gloom case against the mayor four years ago hasn’t panned out.
There have also been some good choices under the radar, particularly with the Housing and Economic Development Bond, and the Cut the Tape initiative, which was well intentioned even if it hasn’t gone as far as it could.
Justin Erb: What did you think of the elected school board when it was proposed? What do you think of it now?
Richard: I had mixed thoughts about it then and mixed thoughts about it now. It is good for people to be engaged in their democracy, and CPS is a huge part of how our city functions. It is also good to have elections in November of even years, and it’s good that that is how these races are being run.
That said, 21 members is an unworkably large board that (perhaps by design), will struggle to provide constructive input or oversight. And I don’t think people are prepared for how challenging it will be to deal with the financial and political entanglements between CPS and the City.
Conor: I was originally pretty split on it. On the one hand, it’s kind of weird that nearly every Illinois school board is elected by the people and CPS wasn’t; on the other hand, my impression was that the proposal for an elected board was less about good governance and more about the CTU pushing for a plan they assumed would enable them to reach more favorable negotiations (by getting their candidates elected) than they could under mayoral control.
Then they got their candidate elected mayor and that kind of flipped on its head (and the CTU has become a lot less popular). Consequently, I’m a bit less worried about that electoral downside than I would have been. I do agree with Richard that 21 members is way too big. It also seems odd that these are all unpaid positions, and to be blunt I can’t fathom why anybody would want the job, given the difficulties they’re going to be facing - but I’m glad a lot of good people are stepping up to run anyways.

To Tex's Question:
The Small Business Bill of Rights and Cut the Tape initiatives will help tremendously, and there’s still a long way to go on the streamline regulations front. Add to that improving customer service for small businesses by streamlining permitting and inspection processes.
Like housing, commercial rents are often out of sync with what businesses can pay these days, plus all costs for most small businesses (especially food businesses) have continued to climb, and we will probably see a significant number of small businesses shutter in the coming year or two. (This will happen across the country—it’s not Chicago-specific.)
More housing will do wonders to support small businesses—more customers, more businesses. Many of our mixed-use neighborhoods were built when the neighborhoods were more densely populated and before big-box stores, supermarkets, and internet retailers. I hate to say this, but in the modern retail economy and with more service-based businesses working from home, we have too many commercial storefronts, especially in less-dense neighborhoods. Adding much, much more housing and converting some ground-floor spaces to residential will alleviate many problems.
As always, thoughtful and informative.
I think we misunderstand the problem with the Chicago Police, if we focus on who is appointed to "lead" and believe that they have any real impact on what is wrong. Eddie Johnson and Snelling obviously quite different people; police culture and job performance...quite the same. CPD does exactly what it wants, runs up 100's of millions of dollars in yearly law suits and simply waits out "leaders" to leave after a couple of years. Its not a public company, or a sports team, or restaurant with new chef.
Not saying that we can't change this, but making this about leadership and personality inhibits change and distracts from the real work.