Ms. Winfrey's Harpo Productions helped transform the old dismal and dangerous skid row into the now chic West Loop. She called Chicago "the most fabulous city in the world" only two months ago, when her season launched in a cast-of-thousands spectacle on Michigan Avenue.

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Chicago is a city of magnificent parks and world-class cultural institutions and universities. But it is also a city of high taxes, regulatory morass and aggressive unions. Is Ms. Winfrey's announcement a wake-up call about underlying problems there? She gave no substantive reasons for it, but her departure is at least the third bitter disappointment to Chicago since it felt itself to be on top of the world--when President Barack Obama gave his victory speech in Grant Park. A month ago, Chicago lost its Olympics bid to Rio; then two major trade shows that had been in the city for decades announced that they were leaving because of the city's extraordinarily high costs and the intractability of the unions.

"Chicago has been punched in the face," says Bob O'Neill, the president of the Grant Park Conservancy. "It would be nice to anticipate and prevent negative things like the loss of the Olympics, the trade shows, and 'Oprah.' We need to retool and understand what happened and what we need to do to change." He believes true change will come only when Chicago reinvigorates its civic and corporate leadership to push for fundamental reform.