The Real Deal Chicago brings us a saga of so much winning. So very much winning.

About a year before the 2005 groundbreaking for Trump International Hotel & Tower, Trump Organization executive Charles Reiss met the late Chicago real estate broker Bruce Kaplan and his colleague, Leslie Karr. The Trump family, Reiss said, wanted advice on how to market the retail space that would face the Chicago River at the tower’s base...“It’s a dreadful space,” said Karr, who is now senior vice president for retail at SVN Chicago Commercial. “You could have some kind of luxury call center there, or maybe a high-end med spa, but not at the prices they were asking.”

A "luxury call center"?

So very much winning.

A decade after the tower opened in 2009, it has just one retail tenant, a salon that occupies an enclosed 3,400-square-foot suite above the hotel lobby. The entire deck-level space remains empty, its blank beige walls on full display for the millions of tourists who stroll along the river each year. No part of it has ever been leased, according to Trump Organization tax appeal documents filed in Cook County and analyzed by The Real Deal.

Trump Tower’s failure is an outlier in Chicago’s competitive retail market, where no comparable space has languished on the market for nearly this long. Over the years, the Trumps have cycled through multiple leasing agents without success. Last year, the Trump name was even removed from marketing materials. And then added back again. Last summer, Donald Trump Jr. paid a visit to the property to kickstart leasing activity.

And Sluggo turned things right around, of course.

These efforts have proven futile.

No kidding.

In 2018 alone, the tower’s leasing brokers, RKF and ARC Real Estate, spoke with at least 77 potential tenants — mostly cafe and restaurant operators — to discuss a potential lease, according to the tax appeal documents. All said no.

An organization dedicated to high-end real estate deals is no good at...high-end real estate deals. That's always been the ur-unreality to the reality-show presidency*. And now we have an unoccupied real-estate desert because these clucks found the one inaccessible spot in the middle of some of the most desirable commercial property in the country. They can't rent to anybody because nobody can find the front door of their big empty building.

So very much winning.

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Charles P. Pierce Charles P Pierce is the author of four books, most recently Idiot America, and has been a working journalist since 1976.

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