November 10, 2023

Water Tower Place, an eight-story, 758,000 sq. ft. high-end shopping mall in downtown Chicago, is in the news. 

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Once one of the biggest and most exciting malls in the Midwest, it quietly leaked that the owners are interested in renting out the top five of its eight floors “for purposes other than retail.” 

Not just wealthy shoppers, but even browsing tourists, too, it seems, are staying away in droves.

Chicago could support such a luxury mall once.  The Magnificent Mile was a thrilling destination for generations.  What happened to Chicago’s iconic Michigan Boulevard?  Or to back up even farther — what happened to Chicago?

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Chicago.

The Second City.  The Biggest Airport in the World.  The City of Big Shoulders.  Hog Butcher to the World.

Back when it was The City That Worked, Chicago had a lot of nicknames, and for good reason, before we lost them, one by one.  We were known as a global corporate center, a transportation hub, a theatre district second only to New York, a restaurant destination second to none.

But Chicago has been other things too, all along.  A machine town run by one corrupt party, the Democrats.  A world-famous home of organized crime, from the mafiosi of the Prohibition Era to the drug gangs of today.  A tax and regulatory hell where the government’s share of your income, both above board and under the table, was always painful.

So, living and working in Chicago — and by extension, in Chicagoland — has always been a challenge.  As an employer, you had to charge more for your product, to cover the taxes and graft.  As an employee, you had to be paid more, in salary and benefits, to cover the income tax and property tax, the sales tax and highway tolls.  Everything adds up, making this an expensive place, not just for some of us, but for virtually all of us.

Still, it could be worthwhile.  For a long time — over a century — the math could work, because the advantages outweighed the disadvantages.