David Spielfogel

30. Garry McCarthy 32. Juan Rangel 31 David Spielfogel Age: 35 Occupation: Senior adviser to the mayor, City of Chicago Next Back He may be young, but this ambitious London School of Economics grad has worked everywhere: in the Clinton White House, on Howard Dean’s presidential campaign, and on U.S. Senate bids on behalf of … Read more

Don Thompson

15. Sam Zell 17. Jim Delany 16 Don Thompson Age: 49 Occupation: CEO, McDonald’s Next Back Talk about a tough act to follow. Former McDonald’s honcho Jim Skinner was one of the best CEOs on the planet. The enigmatic Thompson, who got the top job when Skinner retired last summer, is now grappling with slumping … Read more

Douglas Druick

56. Theo Epstein 58. Frederick Waddell 57 Douglas Druick Age: 67 Occupation: President, Art Institute of Chicago Next Back In the digital age, this chief has moved mountains to make AIC the head of the virtual museum pack. Meanwhile, 2012 attendance was a healthy 1.4 million, and his 2013 opener, Picasso and Chicago, has blockbuster … Read more

Tom Wilson

64. James Reynolds Jr. 66. Tyrone Fahner 65 Tom Wilson Age: 55 Occupation: Chairman and CEO, Allstate Next Back The head of the Northbrook-based insurance giant delivered a 45 percent rise in stock price last year, silencing his critics and nabbing him a debut on this list. Photograph: THE ALLSTATE CORPORATION

John Rogers Jr.

17. Jim Delany 19. Eric Lefkofsky 18 John Rogers Jr. Age: 55 Occupation: Chairman and CEO, Ariel Investments Next Back When you’re the head of a firm that manages $5 billion in assets, a civic connector par excellence (see “It’s Cozy at the Top”), and buds with the president, you command an audience when you … Read more

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