Michael Ferro Jr.

68. Richard Driehaus 70. Pat Quinn 69 Michael Ferro Jr. Age: 46 Occupation: Chairman, Wrapports Next Back This moneyman seems bent on conquering the media one property at a time. After having led the consortium that bought the Reader and the Sun-Times (which went on to run a photo spread of his family at a … Read more

Desirée Rogers

83. Anne Pramaggiore 85. Brendan Sodikoff 84 Desirée Rogers Age: 53 Occupation: CEO, Johnson Publishing Co. Next Back She wasn’t invited to the June wedding of Valerie Jarrett’s daughter, but this business-minded media executive tops the invite list for the rest of the city’s high-profile affairs. Photograph: SHAUNA BITTLE/CHICAGO TRIBUNE

Andrew Mason

99. Anita Alvarez 100   Andrew Mason Age: 32 Occupation: CEO, Groupon Back When news that your board didn't fire you causes your company's share price to fall still farther, you're a clout-challenged CEO indeed. Many blame Mason for Groupon's transformation from white-hot IPO to Wall Street whipping boy; 2013 will be his make-or-break year. … Read more

Tom Ricketts

44. James Crown 46. Dan Webb 45 Tom Ricketts Age: 49 Occupation: Chairman, Chicago Cubs Next Back In January, this longtime Cubs fan (who met his future wife in the Wrigley bleachers) announced that his family would pony up the bulk of his proposed $300 million Wrigley renovation—if the city and others would relax restrictions … Read more

Matt Hynes

77. Robert Clifford 79. Barbara Byrd-Bennett 78 Matt Hynes Age: 41 Occupation: Director, Office of Legislative Counsel and Government Affairs, City of Chicago Next Back The mayor’s top political adviser and chief lobbyist has kept the City Council docile, helped put his boss front and center in Springfield, and proved to be gifted at the … Read more

Greg Wasson

33. Jeanne Gang 35. Brad Keywell 34 Greg Wasson Age: 54 Occupation: CEO, Walgreen Next Back Bruised from last year’s Express Scripts fiasco—analysts estimate that Walgreen’s contract dispute with the giant employee-benefits firm resulted in $4 billion of lost revenue—this former pharmacist needs a big win. Good thing he’s not shy about making big bets. … Read more

Karen Lewis

23. Ken Griffin 25. Tom Pritzker 24 Karen Lewis Age: 59 Occupation: President, Chicago Teachers Union Next Back Last year, she proved wrong all those who had dismissed her as a neophyte with a big mouth. The seven-day teachers’ strike she pulled off in September secured her 29,000 devoted union members a contract that delivered … Read more

Dan Webb

45. Tom Ricketts 47. Neil Bluhm 46 Dan Webb Age: 67 Occupation: Chairman, Winston & Strawn Next Back This lawyer’s work ethic and impressive record representing corporate giants (GE, Pfizer, Microsoft) had already earned him a sterling reputation before he waded into the politically charged investigation of Richard Vanecko, the nephew of former mayor Richard … Read more

Toni Preckwinkle

7. Michael Sacks 9. Irene Rosenfeld 8 Toni Preckwinkle Age: 65 Occupation: President, Cook County Board of Commissioners Next Back This reformer has managed to keep her sterling reputation in a town full of tarnished politicos and get stuff done: slashing patronage, halving the county’s $487 million deficit after her first year, and trimming a … Read more

Steve Koch

28. Robert Zimmer 30. Garry McCarthy 29 Steve Koch Age: 57 Occupation: Deputy mayor, City of Chicago Next Back This Wall Street whiz, who once oversaw blockbuster deals for Credit Suisse, was hired last August as Rahm’s top business adviser. Now his fingers are everywhere: from dealing with the pension crisis to negotiating with the … Read more