Let’s face it: there’s something so typical, so on-brand, so Milwaukee of Milwaukee landing a once-in-a-lifetime event like the 2020 Democratic National Convention and then losing it to a global pandemic. Always a bridesmaid, never a bride. I won’t pull the football away from you this time, Charlie Brown. Insert the sound of The Price Is Right losing horn HERE. Sigh.

Yes, the anchored-in-Milwaukee-in-theory-only DNC takes place this week. (The pre-pandemic version was originally scheduled for July.) A victim of COVID-19, the mostly virtual event will feature virtually no delegates, candidates, party luminaries, or media superstars stepping foot on Milwaukee soil. Biden won’t be here. Harris won’t be here. The Obamas won’t be here. Groups of protestors might be milling around some pointlessly closed streets, but that’s about it. Maybe Mayor Barrett will make a speech. Upwards of 50,000 people were once expected to descend on Milwaukee for the DNC; that number is now down to about 1,000. The New York Times accurately described this week’s shindig as a “ghost convention.”

Let’s face something else: this really, really, really sucks. Restaurants, bars, hotels, music venues, retail centers, food halls, liquor stores, strip clubs, and each and every human being living in and around Milwaukee County stood to make bank off the DNC. Fifty thousand people. Fifty thousand events. Untold millions of dollars spewing forth from the convention centers and sports arenas of Downtown Milwaukee and flowing all the way down to the tiniest bars and Airbnbs of Kenosha. It was going to be glorious. We were all gonna be rich!

And now: nothing. Virtually nothing. Shit, the few people who are still coming are being told to avoid bars and restaurants. It’s enough to make your head spin. It’s enough to make you cry.

There’s another loss, too, albeit a less tangible one: Milwaukee’s chance to “tell its story.” The eyes of the world were going to be on Milwaukee during the DNC, we were told, and the city would finally—finally!—be able shrug off its old beer-and-cheese stereotypes and come out as the vibrant and cosmopolitan 21st-century urban paradise that it truly is. Or something like that. Food! Art! Culture! Smiling young people sitting outside! You could see the “378 yummy places to eat during the DNC” listicles from a mile away.

And yet the “Milwaukee telling its story” thing always seemed fuzzy to me. First of all, what story? The dusty story of its founding, filled with typical characters and interesting-only-to-locals details? (“Tonight on CNN: What really happened during the Milwaukee Bridge War of 1845?”) The well-worn story of its political past, a.k.a. the stuff that’s pretty much covered in Wayne’s World? (“It’s the only major American city to have ever elected three socialist mayors!”) There are numerous Twitter threads filled with endless Milwaukee factoids (Carmex was invented here!), and numerous VISIT Milwaukee videos showing off all our quirky quirks (cheese curds!) Are those the stories we were supposed to tell?

And second of all, whose story? In the early stages of this article, I was planning to write from the perspective of the city itself, sharing the kind of story I thought it should tell. I quickly realized that this was a horrible idea. Who am I to speak for an entire city filled with residents who have vastly different experiences than my own? What makes me the expert on what Milwaukee should and should not project to the world? Don’t we usually call on John Gurda for that sort of thing?

I decided to stick to the one Milwaukee story I knew the best: my own. In doing so, I discovered that the evolution of my time here (25 years next fall) seems to run in parallel with the evolution of the city as a whole. Not so much my individual experiences, but my attitude toward Milwaukee, and Milwaukee’s attitude toward itself. It’s a story of low self-esteem and overconfident change, and of eventually finding a state of equilibrium between the two. It’s a story that begins simply:

I moved to Milwaukee because it was a shit hole.

I moved here in 1996, a self-absorbed 18-year-old from Mayville, Wisconsin hoping to become a critically adored filmmaker and/or a universally beloved rock and roll star. (Reader, neither of these things happened.) I chose Milwaukee for a number of reasons, one of them being that, in my mind, it was a dark, dirty, and wonderfully sketchy city. Ah, the romance! This was the home of gritty bars and gritty drunks, of shuttered buildings and hollowed-out industry, of broken dreams and Jeffrey Dahmer. Beer! Bowling! Blacking out! Move to Madison? Didn’t they give you a complimentary hacky sack when you signed your first lease? No thanks. Milwaukee was hard. It was real. I wanted to be hard and real, too.

And for a time (again, in my mind), Milwaukee was hard and real, and I took pride in that. City-sanctioned Milwaukee pride and things like Milwaukee Day, on the other hand, didn’t exist. Milwaukee was a dark joke, a TV news boogeyman, a place folks drove through and around when they weren’t going to Summerfest or Brewers games. At best, it was a perennial underdog, a far-flung Chicago suburb that could never quite play with the big cities. At worst, it was, well, a shit hole. It was the perfect place for an 18-year-old dope like me who wore pleather jackets and who hated himself.

Did this inferiority complex peak in 2012, when VISIT Milwaukee used the slogan “Milwaukee. Think of us as Chicago’s Upper, Upper North Side” to promote the city? Let’s say it did.

But then something happened. Right around the time I realized I would likely spend the rest of my life in Milwaukee (something I was pleased to realize), a whole new group of young transplants started showing up. Incredibly, this group wasn’t attracted to Milwaukee for its perceived awfulness or its hard-scrabble character—they were coming here for the city’s inherent wonderfulness and its endless malleability. Weird!

Here’s me back in 2015, reflecting on that change:

The past five years have seen Milwaukee Pride™ kicking into overdrive. Beyond Milwaukee Day, think of groups like NEWaukee. Think of sites like OnMilwaukee, Urban Milwaukee, and of course, Milwaukee Record. Think of all the local rallies and good feelings surrounding the Bucks. (The Bucks!) What was once a lowly Rust Belt city with little to no prospects has suddenly become a city of reinvention, a city of potential. It’s now a beacon for smiling, urban-loving young people (or so we’re told), lured here by our incredible music (true), incredible music venues (true), incredible restaurants (true), incredible neighborhoods (true), and cheap rent (less true every day). And who can blame them? Put simply, the Milwaukee of today is better than the Milwaukee of yesterday.

You’ll notice some skepticism in the above passage. True to my nature as a self-loathing asshole, I had my doubts about Milwaukee’s “reinvention.” Wasn’t it the same deal as a dozen other “Rust Belt” cities? Wasn’t it whistling past the graveyard, so to speak, of the not-so-distant past? Wasn’t it glossing over the not-so-perfect present? “These days,” I said in 2015, “suggesting that Milwaukee is anything less than the Greatest City On God’s Green Earth, or that it might be, well, a rather typical Midwestern city struggling to find its identity in a post-industrial world, is tantamount to treason.”

Did Milwaukee’s overconfidence peak in 2013, when the city used a Peaches song about oral sex to promote its downtown? Let’s say it did.

Fast forward a few years and I’ve noticed another change. Now, whenever a flashy new amenity like, say, the downtown streetcar is discussed, people are quick to point out Milwaukee’s glaring faults (and not the “gritty” faults I romanticized back in the day). Some of these objections are troll-ish (you’ll never find a more insufferable bunch that fervent streetcar opponents), but the ones that are sincere point to real issues we can no longer ignore: segregation, racial inequality, police brutality. “Study ranks Milwaukee as worst city for African Americans” goes a typical Milwaukee headline. It’s a wake-up call currently playing out on a national scale, and one that has only been magnified in recent months.

And it’s a wake-up call for me, too. “The Milwaukee of today is better than the Milwaukee of yesterday,” I wrote back in 2015. Even with a dash of skepticism, that sounds incredibly short-sighted today. Now, whenever I crow about something new and shiny in Milwaukee, I remind myself of the “two Milwaukees,” and of the work I still need to do as a writer, a publisher, and a person. I’m 42 years old. One of the happy byproducts of getting old is learning to let go of your bullshit and to listen to others for a change. I’m glad I’ve reached that point in my life, and I think Milwaukee has reached that point, too. It couldn’t have come at a better time.

To sum up: It once felt impossible to say anything nice about the city. Then it felt impossible to say anything bad about the city. Now it feels impossible to say anything nice about the city without qualifying that statement with the oft-ugly truth. So maybe that’s the city’s story, if there can possibly be one: a story of change, a story of a city in the middle of a reinvention and in the opening moments of a long-overdue reckoning. A city in flux. A city’s people in flux. A single person in flux.

There’s been a lot of talk about the DNC returning to Milwaukee in 2024. If it does happen—and I hope it does—I’d like to think we’ll have a different story to tell. A better story, with fewer dark moments and overblown pride and more hard-won victories and triumphs of justice. Think of what we can accomplish in four years. Even if the DNC doesn’t return, we shouldn’t pass up the chance to show the world who we are. And if not who we are, who we can be.

About The Author

Matt Wild
Co-Founder and Editor

Matt Wild weighs between 140 and 145 pounds. He lives on Milwaukee's east side.