Bill Daley

71. Jim Franczek Jr. 73. Patrick O’Connor 72 Bill Daley Age: 64 Occupation: Potential gubernatorial candidate Next Back At presstime, he was “seriously considering” running for governor. Been there, heard that. Still, the former commerce secretary, Gore campaign manager, White House chief of staff, lawyer, and banker has connections in spades. Photograph: WILLIAM B. PLOWMAN/NBC … Read more

Dan McCaffery

90. Michelle Boone 92. Richard Posner 91 Dan McCaffery Age: 65 Occupation: Chairman and CEO, McCaffery Interests Next Back Because he controls the fate of a crucial piece of ground—the site of Children’s Memorial Hospital—plus 589 waterfront acres once occupied by U.S. Steel, McCaffery’s development decisions will have an outsize impact on the look of … Read more

Ted Phillips

74. Roger Ebert 76. Andrew McKenna Sr. 75 Ted Phillips Age: 55 Occupation: CEO, Chicago Bears Next Back Phillips is entrusted to run the beloved football franchise, but does he wield the power to bring the Bears back from epic collapse? His New Year’s Eve ditching of coach Lovie Smith for polar opposite Marc Trestman … Read more

Richard Posner

91. Dan McCaffery 93. Jesse Ruiz 92 Richard Posner Age: 74 Occupation: Judge, U.S. Court of Appeals, 7th Circuit Next Back Posner not only decides the most important issues of the day (he overturned Illinois’s ban on concealed weapons in December) but also influences intellectuals nationwide (in The New Republic, he skewered Justice Antonin Scalia’s … Read more

Ed Burke

21. Jeff Smisek 23. Ken Griffin 22 Ed Burke Age: 69 Occupation: Alderman, 14th Ward Next Back Occasionally singed by scandal but never burned, this City Hall lifer has stayed relevant through 43 years and seven mayors. His influence runs wide and deep: ruling the City Council’s finance committee like a feudal lord, chairing the … Read more

Michael Madigan

1. Rahm Emanuel 3. J.B. Pritzker 2 Michael Madigan Age: 70 Occupation: Speaker, Illinois House of Representatives Next Back Want to pass a bill? Go see Madigan. Want to get elected? Better talk to Mike. Arguably as powerful as the mayor, Madigan redrew the legislative map and promptly added seven seats to his majority. He … Read more

Fred Eychaner

48. Ann Lurie 50. Tracy Letts 49 Fred Eychaner Age: 68 Occupation: President and CEO, Newsweb Corp. Next Back He is the man behind the curtain, but this wizard has real power. Eychaner is a publicity-shy radio station owner who declines interviews and photographs but hosts the likes of Barack Obama and Bill Clinton in … Read more

Michael Kasper

58. Frederick Waddell 60. Linda Johnson Rice 59   Michael Kasper Age: 48 Occupation: Lobbyist, Fletcher, O'Brien, Kasper & Nottage Next Back Dubbed "City Hall's new No. 1 lobbyist" by the Sun-Times, Kasper, who doubles as an election lawyer, has seen his clout multiply since a client became mayor (he argued Rahm's residency case). Not … Read more

Anne Pramaggiore

82. Jorge Ramirez 84. Desirée Rogers 83 Anne Pramaggiore Age: 54 Occupation: CEO, ComEd Next Back One of the most plugged-in women in Chicago business, she made the public case last fall for Exelon’s biggest utility to raise rates to support a grid update (the jury is still out). She’s a presence, too, on many … Read more