× Expand Photograph by Chris Naffziger A Walgreen's housed in an historic building in Chicago's Wicker Park neighborhood.

Over the Thanksgiving holiday weekend, cable channel FXX decided to fill its entire schedule with a 600-episode marathon of The Simpsons. The golden years, the early 1990s, feature some of the most inspired social commentary in any medium, including a strangely prescient “Treehouse of Horrors” episode where aliens kidnap President Bill Clinton and Senator Bob Dole, just a week from the election, and replace them with alien imposters, thus assuring the conquest of the United States. The political critique of our increasingly failed two-party system was laid bare, in a cartoon. But before and after are the ubiquitous episodes of Bart and Lisa, seeking the acceptance of their peers by either committing petty crime or choosing to present a fake public persona. The message of The Simpsons was clear: be yourself, and never compromise your values or your self-esteem for acceptance by the “cool kids.”

I was simultaneously catching up on those old episodes while visiting Chicago over Thanksgiving. The old clichés about the competition between St. Louis and Chicago still continue, and while they may make for easy content, the real lesson the Gateway City could learn from the Windy City is an important one about self-confidence. One thing I never notice in Chicago is a particular lack of hope for the future; while the murder epidemic in the city rages on, I always detect a feeling of hope for the future. Chicago is always planning something grand and new, and seems to stand up for itself. Are hundreds of thousands of people being left behind in Chicago? Yes, of course, but that goes for every city in America, from San Francisco to Youngstown, Ohio.

I met up with a friend in Wicker Park, a burgeoning and yes, gentrifying neighborhood on the near northwest side of Chicago, just a 10-minute L ride from the Loop, the central downtown area of the city. Right off the bat, Chicago made an important decision 70 years ago: while allowing for the destruction and displacement of the interstates, it preserved its mass transit, even incorporating it into new highways. St. Louis still seems to have no guilty conscience for destroying its mass transit. Is it any wonder the Chicago Loop thrives and St. Louis’s downtown dies?

While waiting for my friend to arrive on the L, I took a short walk around the intersection of Milwaukee, Damen, and North Avenues (Chicago embraces its triangular intersections, something St. Louis could learn in its treatment of Gravois Avenue). Lo and behold, I glimpsed the most lavish Walgreens I had ever seen in my life, in the confines of an old bank building. Its Beaux-Arts interior and exterior carefully restored, and its interior store shelves fit in well with the original architecture. I remember thinking to myself, St. Louis would never force Walgreens to do this. Walgreens (or insert any multinational corporation here) would say it could not afford to fix up the old “blighted” property, give a campaign donation to the alderman, and proceed to demolish more historic architecture and build the standard, suburban-style Walgreens.

Guess what? Some places in America have more self-esteem that. Chicago and the local alderman knew very well that Walgreens desperately wanted a location at that intersection, and made them fight for the honor. The 8,177-store behemoth, when confronted by a government with a backbone, agreed. I can assure you that the store was packed with customers on Saturday night, and while I don’t have the documentation, I am sure they have already paid off the investment. Questions of gentrification in Wicker Park aside, Chicago has leadership that will stand up to lazy development. Little wonder that the city is where young people flock to after graduation.

I also remembered a Tweet that my friend Mitch Eagles made a month ago, during the hearing for tax abatements and TIFs for the new City Foundry project in Midtown, near the new Ikea. Mitch informed the Twitter universe that Otis Williams, the head of the St. Louis Development Corporation, stated during testimony the following:

× Otis Williams: "In the city of St. Louis, whether we like it or not, it is not a place where people want to be" #TeamTIF #CityFoundry — Mitch Eagles (@73_Carondelet) November 2, 2016

Wow, thanks for the ringing endorsement for our city. In fairness, St. Louis is not competitive (yet) with better-lead cities such as Chicago, Seattle, New York or San Francisco, cities that culturally, politically, and economically capture the imagination of the entire world. But aren’t our leaders supposed to be fighting for us? To have a sometimes unrealistic hope in our future? Back when St. Louis had just been founded, and conditions were so dire that the small village received the nickname Pain Court, literally “short of bread,” do you think that Pierre Laclede and or August Chouteau ever publicly stated that St. Louis was “not a place where people want to be?”

I doubt it. We can learn a lot from Chicago, and other thriving cities in America, about the importance of self-esteem and standing up for ourselves and our community. We can even learn from our founders, whose confidence and hope founded a great city. When will we recapture their imagination, their vision?

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Chris Naffziger writes about architecture at St. Louis Patina. Contact him via email at naffziger@gmail.com.