The Daley Years

"He's lived in a box and it's the City of Chicago," says younger brother Bill, the Clinton-era Commerce Secretary-turned-banker. This inward focus explains the lack of ambition beyond City Hall and six-day work weeks. And it also explains the crushing disappointment Daley felt when the International Olympic Committee convened in Copenhagen to decide among Rio de Janeiro, Tokyo, Madrid or Chicago and ignominiously knocked out Chicago in the first round.

A win would have solidified the city's little-understood position as a world powerhouse. According to Columbia University global cities expert Saskia Sassen, an exhaustive international study of the top 75 global cities ranks Chicago fifth-most economically important, after London, New York, Tokyo, and Singapore, based on a mix of resources, talent and state of the art office districts needed by national and foreign firms operating worldwide.

Who knew? "It's also the most beautiful city in the U.S.," says Sassen. "My European friends and colleagues are stunned when they go."

An Olympic nod would have also helped shatter caricatures about Chicago and provided the engine for its next stage of development. And it would have capped a remarkable run for Daley, whose success came in the face of urban America's basic social and economic ills. It would have sealed his legacy and served as tributes to his dad, the Builder; a son, Kevin, who died of spina bifida and whom he mentioned in his announcement; and his wife, Maggie, by all accounts the critical force in keeping the emotional, at times erratic, mayor, on an even keel but now struggling with inoperable breast cancer. She held his hand as Daley revealed his decision not to run for re-election to a sparse group of reporters Tuesday.

In retrospect, a tipoff may have been how a man who has mastered the local and Washington political processes, improbably avoided the quicksand of corruption around him and won six straight elections couldn't conquer an electorate over whom he had scant control: the often unpredictable Olympic panel. And he had to rely on the celebrity and aura of a man who, more than Daley or Michael Jordan or Oprah Winfrey (who announced she's leaving town next year), symbolizes the reality of a new century's cool, sophisticated Chicago even as he owes Daley precious little: President Barack Obama.

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James Warren is the Chicago editor of The Daily Beast and an MSNBC analyst. He is the former managing editor of the Chicago Tribune.

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