Robert Falls

68 Robert Falls Age: 59 Occupation: Artistic director, Goodman Theatre Still provocative after 28 years at the helm of Chicago’s most prominent theatre (in last year’s acclaimed production of Measure for Measure, he killed off a character who wasn’t supposed to die), Falls has audiences eating out of his hand. Last season, the shows on the … Read more

Dan Webb

69 Dan Webb Age: 68 Occupation: Chairman, Winston & Strawn This former U.S. attorney remains the go-to litigator for white-collar defendants across the land. As the special prosecutor, Webb won a major victory in January when a judge refused to dismiss the manslaughter case against Richard Vanecko, the nephew of former mayor Richard M. Daley. (Vanecko … Read more

Michelle Boone

70 Michelle Boone Age: 52 Occupation: Commissioner, Department of Cultural Affairs and Special Events, City of Chicago The mayor’s culture czar helped the Taste of Chicago turn a profit in 2013—for the first time in six years—and moved the Chicago Jazz Festival from the Petrillo Music Shell to Millennium Park, a leap in elegance and acoustics. … Read more

James Heckman

71 James Heckman Age: 69 Occupation: Professor of economics, University of Chicago Last year, President Obama announced the White House’s support of universal pre-K. Then the new mayor of New York, Bill de Blasio, ran on an identical idea. And Hillary Clinton, likely the 2016 Democratic nominee for president, recently launched an initiative for early childhood … Read more

Greg Goldner

72 Greg Goldner Age: 44 Occupation: CEO, Resolute Consulting Goldner took a bit of a hit in 2013 when City Hall cut ties with his client Redflex Traffic Systems, the city’s red-light camera provider, after a bribery scandal. Nevertheless, the longtime Democratic operative and CEO of the public affairs powerhouse Resolute Consulting remains an influential mayoral … Read more

Jeff Tweedy

75 Jeff Tweedy Age: 46 Occupation: Musician Lately, Wilco’s frontman has been spreading the magic—as a producer. His assured touch in sessions with Mavis Staples, Low, and Sarah Lee Guthrie and Johnny Irion earned him a 2013 Grammy nomination for producer of the year (he lost to golden boy Pharrell Williams). Coming this year: a new … Read more

Robert Clifford

76 Robert Clifford Age: 62 Occupation: Founder and principal partner, Clifford Law Offices In 2013, Clifford’s prestigious boutique personal injury firm won a total of $66.9 million in 13 cases, including a $15.5 million lawsuit against University of Chicago Medicine. With elections on the horizon, all the major Democratic pols, from Hillary Clinton on down the … Read more

Dan McCaffery

84 Dan McCaffery Age: 67 Occupation: Chairman and CEO, McCaffery Interests He controls the 500-acre Lakeside development, the city’s next power nexus. Photo: Laura Brown Photography

James Crown

55 James Crown Age: 60 Occupation: President, Henry Crown & Co. The son of billionaire Lester Crown (No. 18) had a rough year. The president of his family’s private investment firm, he also chairs the JPMorgan Chase risk committee responsible for the trading fiasco known as the London Whale, which generated $6 billion in initial losses … Read more

How We Made This List

How do you define power? For the purpose of compiling this list—Chicago’s third annual ranking of the 100 most powerful Chicagoans—we started with proximity. (You don’t spend most of your time in the area? No dice. Sorry, President Obama.) You need not boast riches, pedigree, or position, though those things can help. You must have … Read more