One possible progressive reckoning hot take: Mayors can't ignore "trade-offs," specifically, with local oligarchs, even though taking oppositional or hostile positions in relation to the local corporate order are how Dems or progressives often get elected these days. And for good reason, the corporate order is a kind of austerity extortion trap. Talk about taxing the rich and the rich will threaten to move to some red state tax haven. Mayors need to tax and regulate stuff to build prosperity but business people don't like taxes or regulations, and are always looking for ways to get out of them. It's a conundrum. Successful mayors finesse the billionaires, getting them to buy into some big growth projects; with which the biz guys will own a substantial piece, naturally. But these mayors are rare. Most mayors shuffle around within the generally recognized "business friendly" norm confines of not talking about taxing or regulating the rich. Or until voters get fed up and vote in the next liberal progressive mayor who will be trashed as not knowing how to collaborate and find compromises and do the necessary trade-offs of city governance. Such as not talking about taxing or regulating the rich. But what if, actually, the biggest obstacle to better city living isn't environmental red tape and NIMBY zoning laws but insufficiently taxing and regulating the rich?
I am not a Chicagoan, so I’m not up on details regarding Mayor Johnson’s overall record. It seems his current unpopularity offers lots of lessons for big city mayors, whether they are self-described ‘progressives’ or not.
But I think the way Johnson’s handling of the migrant issue is framed is unfair. It’s a rare candidate who could have come into office with a background that would have prepared her/him for an influx of unhoused, unemployed, non-English-speaking people the size of a small city. In fact, that was the whole point of that political stunt, wasn’t it? Maybe the winterized tents were a bad idea, and maybe the social service contracts could have been negotiated for less than $200/hour. But what was the alternative? Leaving families to fend for themselves, living in bus stations and sidewalks with no services or support? In NYC, Mayor Adams got burned for initially housing migrants in vacant hotels until shelters were constructed. Not a great solution either (though the hotel owners made out OK). But again –was there a better option?
This is exactly what Abbot and DeSantis counted on by using human beings to highlight a policy failure that was decades in the making. And as a bonus, the MAGA crowd also got to strengthen their politically potent wedge strategy of creating resentment over the false narrative that migrants are taking scarce resources from existing communities in need.
By all means let’s examine Johnson’s weaknesses in governance and managing budget tradeoffs. But when it comes to the migrant issue, it’s important to reflect on the context. Given the success of the send-the-migrants-to-blue-cities stunt, it’s likely something like it will be used again, perhaps in a different way with a different issue. Is anyone in Democratic/progressive upper echelons working on possible scenarios? I hope so.
Excellent analysis. I lived in Chicagoland (just outside the city) for many years and this tracks well with what I've observed and what I hear from friends.
The only important point that I think was rather neglected (although it was mentioned in passing) is that the state of Illinois, Chicago, and more than a few other Illinois municipalities and counties are engaging in this kind of performative politics in the shadow of a mountainous public pension overhang that gets bigger, darker, and less sustainable every year. Stemming and reversing population loss and tax base erosion isn't just a nice-to-have in this situation: it's a desperate need-to-have. So is pension reform, but "the Mayor from the (already widely discredited) CTU" is the last person to be expected to push THAT.
There's a Greek tragedy of statewide proportions taking shape in the Land of Lincoln, but the comedians won't get off the stage.
All kidding aside, it looks like conservatives have a new use for "Let's Go Brandon". If the Left continues to be tone-deaf with candidates and policies that are so inept, it is only to the Right's benefit.
I was once on a university faculty union board of directors. Any union that only spends 20% on member representation needs to be decertified.
> Johnson compared those who questioned the legitimacy of some of the union demands to members of the Confederacy who opposed the abolition of slavery.
Ahhhhhh, there's the identitarian progressivism I remember from the late 2010s!
I have been reading these comments multiple times a day because I have two kids living in Chicago for school, and at least one intends to stay there after her graduation in a couple of weeks. I have very much fallen in love with Chicago after visiting a lot over the past 4 years, and my husband and I have talked about retiring there in another decade if at least one of our kids is there. But its mismanagement makes us nervous. It is a behemoth of a city, and I am not sure how to get it under control.
I was also surprised to see that it is losing population because, unless you find an individual landlord who only owns a unit or two, moving in Chicago, even in the crappy neighborhoods, is expensive. Instead of security deposits, there are massive move-in fees that you don't get back, and in many cases, it is not clear what you get for the fee because the apartments are a mess when you move in. https://blockclubchicago.org/2025/04/23/chicago-landlords-are-charging-hundreds-in-move-in-fees-renters-want-to-know-why/
BTW, the news source that the article I linked to above is an old school, boots-on-the-ground news outlet, even though it is relatively new and all online. If you are interested in all things Chicago, I recommend Block Club Chicago. https://blockclubchicago.org/
The move-in fees are because of a quirk in Chicago security deposit laws. Landlords not only have to not commingle funds, they also have to pay a certain interest rate, and if they slightly mess any of that up there are serious penalties to the landlord. As a result, the smart move is to charge a move-in fee.
That is what everyone tells me, but it sounds like a sorry excuse to my ears. Until recently, I thought it was that way everywhere. It was the rule in Boston when I first rented there in the early 1990s. In fact, my landlord probably thought he could put one over on me by just giving me back my security deposit. Then I mentioned that he had not been giving me the annual interest payments on my security deposit in escrow. When I moved out, the check he gave me miraculously included an amount well above my deposit plus interest.
It sounds like the answer is to modify the penalties, not this stupid move in fee.
I completely understand your love of Chicago. I love the city, too, but after over 20 years of living there, I wouldn't consider moving back. Before you do, please check the financials of the state, the county (Cook), and the city as carefully as you would those of a Florida condominium that you were thinking of buying into, and go with your heads, not your hearts. All the best!
I will admit upfront that this piece is a bit too consistent with my ideological priors for me to evaluate it objectively. That said, Ben this was fantastic, and I think that’s well reflected in the attention it’s receiving outside the confines of SlowBoring. Seriously well done!
Great piece Ben! I think you get at the challenge for many ideologies that work well as a critique but not as a management system. Leading progressive thinkers tend to come out of academia or the legislative branches of politics where you don't have to grapple with "what if I actually ran a complex organization in accordance with these principles?" As a new-ish manager, there's just a whole reason of trade-off management and rule enforcement that it seems like many in that wing of the party have little practical experience with. I genuinely hope progressives come up with ways to identify better leaders and equip them with the tools necessary not just to win elections but to govern after the victory.
Polling will ask Black voters in Chicago what their most important issues are and they'll say jobs, cost of living, school quality the migrant crisis, etc and then vote like 90% for Johnson.
As the article points out, though, they weren't offered much of a choice. And after feeling disrespected (if pretty well-governed) by Rahm Emanuel and suffering four lost years under Lori Lightfoot, a lot of folks were feeling desperate.
If someone has a moderate neolib recommendation for Detroit mayor I'm all ears. But the primary isn't until August so I haven't paid close attention yet and most likely I'll just vote for whoever Mayor Duggan endorses.
The timing of this post is funny because Matt just posted something on Bluesky about progressives accusing slightly less progressive people of being Trump voters and seeing all the lefties attempt to dunk on it as a made up thing immediately made think of the Johnson-Vallas election.
I live in the 25th ward and saw first hand how bad an alderman one of his key allies—Byron Sigcho-Lopez—was and couldn’t vote for Johnson. I held my nose and voted for Vallas but it was common for people to conflate him with Trump. Even since then, I’ve gotten CTU and its related allies sending mailers accusing moderate school board candidates of being secret Republicans/Trumpy. It’s not good! Has it made me vote Republican? No, but it has made me even more reflexively skeptical of progressive candidates. I’m also several degrees to the left of the median voter, if that wasn’t the case it seems pretty plausible it may push some over the line towards Trump. That may make progressives feel good but it sure as shit doesn’t win elections.
The essential problem with Blue governance in big cities is here:
"How can Chicago build affordable housing more efficiently to reduce homelessness? How can the city add housing supply in its highest-demand neighborhoods to increase population growth? Can the teachers’ union temper its budget demands and embrace higher standards to improve student outcomes? Which policing investments will reduce homicide rates while building community trust?"
Not a word about supporting and growing the city's economy, or providing the quality services that the non-dependent population that pay into the city's tax base need in order to make it worthwhile for them to stay there. It's the same in New York. The whole principle of the City Council's existence is who gets to spend what on the social projects they like (they call this "investments"). None of them know anything or care anything about governance. It's just basically government by graft, which as we now know is the essence of the national Democratic Party as well.
It's all very well to say "you know, we've got to start showing the nation that we can do a good job in the Blue constituencies that we control" but actually doing that goes against everything the party stands for. It's never going to happen. The only hope there good, old-fashioned two-party government, that is, for the Republicans to make a serious play for those voters.
i live in Philadelphia, another big northern city. Our new mayor, Cherelle Parker, was the most conservative Democrat running. She emphasizes public safety, being”clean” and green. It seems to be working! She also seems to understand the importance of making it easier to do business in Philly. I dont see a lot of national press on Parker (which may be a good thing).
At some point, I predict the Illinois Governor is going to have to take over Chicago governance, as Michigan did with Detroit after decades of mismanagement. I hope he is up to the task.
Illinois is in almost as parlous a financial condition as Chicago, so there's little help to be hoped for there. In addition, Chicago dominates its state in a unique way: Michigan and even New York don't compare. So the state taking over Chicago would usually just mean one group of Chicago politicians taking over from another group of Chicago politicians.
I would like to see the power of both the teachers union and the police union greatly reduced. Both are a blight driving up costs with both ineffective at their jobs.
My first reform - let them all move out of the city if they wish. I'm certain that plenty of the rank and file would bolt.
Second, remove the right of teachers to strike during the school year.
One possible progressive reckoning hot take: Mayors can't ignore "trade-offs," specifically, with local oligarchs, even though taking oppositional or hostile positions in relation to the local corporate order are how Dems or progressives often get elected these days. And for good reason, the corporate order is a kind of austerity extortion trap. Talk about taxing the rich and the rich will threaten to move to some red state tax haven. Mayors need to tax and regulate stuff to build prosperity but business people don't like taxes or regulations, and are always looking for ways to get out of them. It's a conundrum. Successful mayors finesse the billionaires, getting them to buy into some big growth projects; with which the biz guys will own a substantial piece, naturally. But these mayors are rare. Most mayors shuffle around within the generally recognized "business friendly" norm confines of not talking about taxing or regulating the rich. Or until voters get fed up and vote in the next liberal progressive mayor who will be trashed as not knowing how to collaborate and find compromises and do the necessary trade-offs of city governance. Such as not talking about taxing or regulating the rich. But what if, actually, the biggest obstacle to better city living isn't environmental red tape and NIMBY zoning laws but insufficiently taxing and regulating the rich?
I am not a Chicagoan, so I’m not up on details regarding Mayor Johnson’s overall record. It seems his current unpopularity offers lots of lessons for big city mayors, whether they are self-described ‘progressives’ or not.
But I think the way Johnson’s handling of the migrant issue is framed is unfair. It’s a rare candidate who could have come into office with a background that would have prepared her/him for an influx of unhoused, unemployed, non-English-speaking people the size of a small city. In fact, that was the whole point of that political stunt, wasn’t it? Maybe the winterized tents were a bad idea, and maybe the social service contracts could have been negotiated for less than $200/hour. But what was the alternative? Leaving families to fend for themselves, living in bus stations and sidewalks with no services or support? In NYC, Mayor Adams got burned for initially housing migrants in vacant hotels until shelters were constructed. Not a great solution either (though the hotel owners made out OK). But again –was there a better option?
This is exactly what Abbot and DeSantis counted on by using human beings to highlight a policy failure that was decades in the making. And as a bonus, the MAGA crowd also got to strengthen their politically potent wedge strategy of creating resentment over the false narrative that migrants are taking scarce resources from existing communities in need.
By all means let’s examine Johnson’s weaknesses in governance and managing budget tradeoffs. But when it comes to the migrant issue, it’s important to reflect on the context. Given the success of the send-the-migrants-to-blue-cities stunt, it’s likely something like it will be used again, perhaps in a different way with a different issue. Is anyone in Democratic/progressive upper echelons working on possible scenarios? I hope so.
Excellent analysis. I lived in Chicagoland (just outside the city) for many years and this tracks well with what I've observed and what I hear from friends.
The only important point that I think was rather neglected (although it was mentioned in passing) is that the state of Illinois, Chicago, and more than a few other Illinois municipalities and counties are engaging in this kind of performative politics in the shadow of a mountainous public pension overhang that gets bigger, darker, and less sustainable every year. Stemming and reversing population loss and tax base erosion isn't just a nice-to-have in this situation: it's a desperate need-to-have. So is pension reform, but "the Mayor from the (already widely discredited) CTU" is the last person to be expected to push THAT.
There's a Greek tragedy of statewide proportions taking shape in the Land of Lincoln, but the comedians won't get off the stage.
All kidding aside, it looks like conservatives have a new use for "Let's Go Brandon". If the Left continues to be tone-deaf with candidates and policies that are so inept, it is only to the Right's benefit.
I was once on a university faculty union board of directors. Any union that only spends 20% on member representation needs to be decertified.
> Johnson compared those who questioned the legitimacy of some of the union demands to members of the Confederacy who opposed the abolition of slavery.
Ahhhhhh, there's the identitarian progressivism I remember from the late 2010s!
I have been reading these comments multiple times a day because I have two kids living in Chicago for school, and at least one intends to stay there after her graduation in a couple of weeks. I have very much fallen in love with Chicago after visiting a lot over the past 4 years, and my husband and I have talked about retiring there in another decade if at least one of our kids is there. But its mismanagement makes us nervous. It is a behemoth of a city, and I am not sure how to get it under control.
I was also surprised to see that it is losing population because, unless you find an individual landlord who only owns a unit or two, moving in Chicago, even in the crappy neighborhoods, is expensive. Instead of security deposits, there are massive move-in fees that you don't get back, and in many cases, it is not clear what you get for the fee because the apartments are a mess when you move in. https://blockclubchicago.org/2025/04/23/chicago-landlords-are-charging-hundreds-in-move-in-fees-renters-want-to-know-why/
BTW, the news source that the article I linked to above is an old school, boots-on-the-ground news outlet, even though it is relatively new and all online. If you are interested in all things Chicago, I recommend Block Club Chicago. https://blockclubchicago.org/
The move-in fees are because of a quirk in Chicago security deposit laws. Landlords not only have to not commingle funds, they also have to pay a certain interest rate, and if they slightly mess any of that up there are serious penalties to the landlord. As a result, the smart move is to charge a move-in fee.
That is what everyone tells me, but it sounds like a sorry excuse to my ears. Until recently, I thought it was that way everywhere. It was the rule in Boston when I first rented there in the early 1990s. In fact, my landlord probably thought he could put one over on me by just giving me back my security deposit. Then I mentioned that he had not been giving me the annual interest payments on my security deposit in escrow. When I moved out, the check he gave me miraculously included an amount well above my deposit plus interest.
It sounds like the answer is to modify the penalties, not this stupid move in fee.
I completely understand your love of Chicago. I love the city, too, but after over 20 years of living there, I wouldn't consider moving back. Before you do, please check the financials of the state, the county (Cook), and the city as carefully as you would those of a Florida condominium that you were thinking of buying into, and go with your heads, not your hearts. All the best!
Great source when researching.
I will admit upfront that this piece is a bit too consistent with my ideological priors for me to evaluate it objectively. That said, Ben this was fantastic, and I think that’s well reflected in the attention it’s receiving outside the confines of SlowBoring. Seriously well done!
Great piece Ben! I think you get at the challenge for many ideologies that work well as a critique but not as a management system. Leading progressive thinkers tend to come out of academia or the legislative branches of politics where you don't have to grapple with "what if I actually ran a complex organization in accordance with these principles?" As a new-ish manager, there's just a whole reason of trade-off management and rule enforcement that it seems like many in that wing of the party have little practical experience with. I genuinely hope progressives come up with ways to identify better leaders and equip them with the tools necessary not just to win elections but to govern after the victory.
Polling will ask Black voters in Chicago what their most important issues are and they'll say jobs, cost of living, school quality the migrant crisis, etc and then vote like 90% for Johnson.
As the article points out, though, they weren't offered much of a choice. And after feeling disrespected (if pretty well-governed) by Rahm Emanuel and suffering four lost years under Lori Lightfoot, a lot of folks were feeling desperate.
If someone has a moderate neolib recommendation for Detroit mayor I'm all ears. But the primary isn't until August so I haven't paid close attention yet and most likely I'll just vote for whoever Mayor Duggan endorses.
The timing of this post is funny because Matt just posted something on Bluesky about progressives accusing slightly less progressive people of being Trump voters and seeing all the lefties attempt to dunk on it as a made up thing immediately made think of the Johnson-Vallas election.
I live in the 25th ward and saw first hand how bad an alderman one of his key allies—Byron Sigcho-Lopez—was and couldn’t vote for Johnson. I held my nose and voted for Vallas but it was common for people to conflate him with Trump. Even since then, I’ve gotten CTU and its related allies sending mailers accusing moderate school board candidates of being secret Republicans/Trumpy. It’s not good! Has it made me vote Republican? No, but it has made me even more reflexively skeptical of progressive candidates. I’m also several degrees to the left of the median voter, if that wasn’t the case it seems pretty plausible it may push some over the line towards Trump. That may make progressives feel good but it sure as shit doesn’t win elections.
The essential problem with Blue governance in big cities is here:
"How can Chicago build affordable housing more efficiently to reduce homelessness? How can the city add housing supply in its highest-demand neighborhoods to increase population growth? Can the teachers’ union temper its budget demands and embrace higher standards to improve student outcomes? Which policing investments will reduce homicide rates while building community trust?"
Not a word about supporting and growing the city's economy, or providing the quality services that the non-dependent population that pay into the city's tax base need in order to make it worthwhile for them to stay there. It's the same in New York. The whole principle of the City Council's existence is who gets to spend what on the social projects they like (they call this "investments"). None of them know anything or care anything about governance. It's just basically government by graft, which as we now know is the essence of the national Democratic Party as well.
It's all very well to say "you know, we've got to start showing the nation that we can do a good job in the Blue constituencies that we control" but actually doing that goes against everything the party stands for. It's never going to happen. The only hope there good, old-fashioned two-party government, that is, for the Republicans to make a serious play for those voters.
Detached single family houses in the neighborhoods people actually want to live in are not selling for $350,000. I wish.
That number is totally skewed by the sale price of tear-downs in high crime neighborhoods.
i live in Philadelphia, another big northern city. Our new mayor, Cherelle Parker, was the most conservative Democrat running. She emphasizes public safety, being”clean” and green. It seems to be working! She also seems to understand the importance of making it easier to do business in Philly. I dont see a lot of national press on Parker (which may be a good thing).
At some point, I predict the Illinois Governor is going to have to take over Chicago governance, as Michigan did with Detroit after decades of mismanagement. I hope he is up to the task.
Illinois is in almost as parlous a financial condition as Chicago, so there's little help to be hoped for there. In addition, Chicago dominates its state in a unique way: Michigan and even New York don't compare. So the state taking over Chicago would usually just mean one group of Chicago politicians taking over from another group of Chicago politicians.
I would like to see the power of both the teachers union and the police union greatly reduced. Both are a blight driving up costs with both ineffective at their jobs.
My first reform - let them all move out of the city if they wish. I'm certain that plenty of the rank and file would bolt.
Second, remove the right of teachers to strike during the school year.