Menu Home

On My 21st Chicagoversary, I No Longer Have Faith in Chicago

I have no faith left in Chicago. On the 21st anniversary of my move to Chicago from my native New York City (which also nearly marks this blog’s 19th birthday), bringing my Chicago era to an end cannot come fast enough. And the saddest part is that in 2024, I’m far from the only Chicagoan who has no hope for a Chicago future where the city doesn’t end up looking like the Detroit of the past. Because Detroit has a lot going for it right now—consistent development, local megaprojects, new investment, fiscal health, increasingly great student math and reading scores, a downtown residential renaissance.

Meanwhile, we in Chicago have had two consecutive mayors going to war with businesses, restaurants, developers, and the news media, delegitimizing the concerns of White and Hispanic residents, systematically ignoring crime and dismantling the police force and policing tools, ignoring both the needs and impact of newly arriving refugees, allowing deadweight leadership to destroy a world-class transit system–and in the case of Brandon Johnson, shitting on more than a century of protecting our lakefront as a bedrock civic policy, being an overt and active antisemite, and being a completely inept political pawn.

None of that is new news. Every single major investor, developer, philanthropist, and corporation that has yanked their headquarters and their money from Chicago to elsewhere has cited these things, over and over and over. I’m thrilled we’ll soon have a state’s attorney who actually prosecutes crime. But that change is still months away. In the meantime, we’re left with a mayor who, incredibly, is even more toxic to the socioeconomic health and future of this city than the chronically wagging-fingered Lori Lightfoot was.

The Chicago I moved to in 2003, with its safe, livable downtown, vibrant neighborhoods where people didn’t fear to stroll from day into dusk, drive after dark, or take transit at all, with a City Hall that was a City Hall for Chicagoans of all colors, ethnicities, and backgrounds? The Chicago that wasn’t an international punch line? The one where you still felt secure about having a social life beyond daylight hours? Raising your kids? Growing old?

When was the last time you felt or thought any of those things about Chicago? How long before the pandemic did you realize Chicago was in trouble? Was it 2019, right before the world shutdown? Or 2016, when Kim Foxx stopped prosecuting shoplifters, muggers, and carjackers? For me, Foxx was the beginning of the end. But I held out hope and stayed put—through years of a plague wondering if we’d survive at all. Through all of Lightfoot’s pandering buffoonery. Because I’ve loved this city since the day I arrived, and thought it was worth the faith of biding time.

But how many years of your life should you wait for your city’s leadership to stop toxically destroying it before you realize those years could have been spent happier, safer, and less stressed out in other places that don’t have leaders who’ve decided to turn their cities into social experiments? When what you really deserved all along was simply to be able to walk to the corner for a beef and a coke without wondering if you’d make it back safely or at all?

Making an entire city as weak as its weakest neighborhoods will never lead to anywhere but hell. Supporting and nurturing what’s already working and helping that to grow and spread is a much better strategy, and the one that created the Chicago of the very recent past whose future is being irreparably destroyed.

This current Chicago, where after two consecutive Black Progressive mayors, every neighborhood gets to enjoy the fear and dread that before them only our worst neighborhoods got dragged down by? With that spread of dread being a point of political pride? “Look world–now everyone’s afraid to go out at night and all our philanthropists are moving to Miami!” What kind of fucked-up value signal is that?

It didn’t make our worst neighborhoods any safer, nor did it somehow teach our best neighborhoods some sort of lesson in identity politics. It just motivated the people and businesses with the money and skills that Chicago needs and has relied upon since its founding—investors and corporate leaders and residents alike—to leave, and made the ones who have always considered new lives here to reconsider coming at all. Whether anyone who isn’t them likes it or not.

No one owes Chicago a life here. Chicago doesn’t deserve anyone’s residency. Being a Chicagoan is a privilege that works both ways. It can be wonderful to have this place as your home. But the city is also enriched by those who stay. And staying is a choice. No matter how much Chicago needs all of its Chicagoans, the city can’t stop those who choose to flee for the sake of their own wellbeing. Endless mayoral tantrums full of class-shaming shouts of how dare you, and you owe it to residents less privileged than you, and your ZIP code means you don’t have real problems–and the ever popular but they’re just youth? Will never get a single person to stay.

They just remind the people who’ve decided to leave why they’re leaving.

Any why shouldn’t they? Why should people with means and choice keep wasting their safety and their nerves on a place that persistently and very publicly doesn’t care about their welfare? Especially when it doesn’t take very much in the way of means to go? If you really and truly want to get the hell out of Chicago, maxxing out the credit cards in your wallet and the cargo area in your SUV are pretty much all you need to do. More than 80,000 former Chicagoans have done it since 2020.

When I left New York for Chicago in 2003, I spent two solid years blissfully running around, checking off my bingo card of neighborhoods, restaurants, foodways, museums, gardens, and tourist attractions that to this day I believe were consistently on par with or better than the ones I left behind in the alleged capital of the world. I spent most of the next two decades happy that I lived on the southwestern shore of Lake Michigan, warmed by the sight of our skyline every time I returned by road, rail, or air. Which to this day I still point out never, ever happened to me one time upon returning to my native New York. (This weekend, in fact, I remarked this very thing to Ryan on the way back from Michigan wine country when the Loop came into view as we crossed the Skyway from Indiana.)

I have turned down job opportunities that would have brought me back “home” to New York. I reunited with my family after many years and still stayed put in this time zone. And although you may not believe it reading this, I don’t regret moving here and I don’t regret any of the time I’ve spent here. Not at all.

But moving here was in my thirties. Being here now is in my fifties. And there many things I want to accomplish, do, see, enjoy, celebrate, and be while I’m still on this planet that quite frankly I deserve to accomplish, do, see, enjoy, celebrate, and be without looking over my shoulder every goddamned time I walk out my front door. (Chicagoan reading this, you deserve that too, by the way.)

Enough is enough when it’s enough. There will be a day when you’ll get a blog update in your inbox or in your socials and read about where Ryan and I eventually decided to be–after we’re there. I won’t telegraph it and I have never been one for goodbyes. My transitions have always been like light switches. The stress-avoidant autistic in my likes it that way. I’m not saying my exit from Chicago will be tomorrow. But I am saying, with certainty, that it will be, and sooner rather than later. Until then, like the rest of us, I’ll do my best to keep my head down and make the best of it. 

The inevitableness I feel about it reminds be of what Democratic Pennsylvania senator John Fetterman said about the far-left Progressive movement. He takes pains to point out that he didn’t leave that wing of his political party. With all of its ideological change—change that he finds toxic—the movement really left him. 

Riding that magic carpet out of town is a lot less bittersweet when the rug’s already been pulled out from under you.

Categories: Backstory Blog Anniversaries CHICAGO Politics

Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

My Bio | My Conversion | My Family Reunion

Follow My Socials:

Contact Me:

1 reply

  1. As I pondered the affordability and cacophony of Los Angeles for one newly retired, coming back to my beloved Chicago was certainly high on my list. I just didn’t think I could adjust to a place where the life of an adult playground had been sucked out.
    So I chose the mountains of Western North Carolina, and the Asheville metropolis (!). Many out-of-town progressives are coming here; I can always visit , but I hear the Dearborn Social Club is gone…

Leave a comment...