Occupation: Chairman, Equity Group Investments
He's the richest person in Chicago, with a net worth of $3.8 billion, according to Forbes. But his wealth alone does not secure him a spot on this list. Demonstrating an uncanny ability to emerge relatively unscathed from business disaster (Tribune, anyone?), the polarizing mogul is as busy as ever with the real-estate empire (apartments, mobile home parks, overseas properties) that he founded and controls. He's also helping shore up the Museum of Contemporary Art, having contributed $10 million in October that the institution will use, in part, to pay down its debt.
Photograph: CHARLES OSGOOD/CHICAGO TRIBUNE