Michael Kasper

82 Michael Kasper Age: 49 Occupation: Lobbyist and attorney, Fletcher, O’Brien, Kasper & Nottage Kasper is quietly clout heavy. He is a close adviser to the mayor and one of the most powerful lobbyists in the state—his client roster is loaded with corporate titans, who are paying for Kasper’s inside access to Madigan (No. 2), his … Read more

James Franczek

79 James Franczek Age: 67 Occupation: Attorney, Franczek Radelet Mayor Emanuel’s first choice for difficult labor contract negotiations had his hands full last year with the city police union. Talks stalled late in 2013 when union leaders called the mayor’s wage offer an insult. Touch-and-go situation? Go to Franczek.

Tom Wilson

81 Tom Wilson Age: 56 Occupation: Chairman and CEO, Allstate The Northbrook-based insurance giant Wilson runs doesn’t loom quite so large anymore. Geico recently toppled Allstate as the nation’s second-biggest auto insurer—helping push his rank on this list down from No. 65 last year. The pressing question now: Can the bespectacled Michigan native get the business … Read more

Mike Madigan

2 Mike Madigan Age: 71 Occupation: Speaker, Illinois House Madigan clings to his No. 2 spot on this list, but barely. In 2013, he was hounded by a Metra patronage scandal and embarrassed by a rare public feud with Attorney General Lisa Madigan (No. 52), his daughter, over her much-anticipated candidacy for governor, which he squashed. … Read more

Gigi Pritzker

85 Gigi Pritzker Age: 51 Occupation: Founder and CEO, OddLot Entertainment A “movie mogul rising,” according to The New York Times, in November this producer (and sister of Tom Pritzker, No. 22) released her biggest film yet: Ender’s Game, a sci-fi adventure starring Harrison Ford, made for a reported $110 million (it took in $61.7 million … Read more

Pat Quinn

50 Pat Quinn Age: 65 Occupation: Governor, State of Illinois Like Sam Zell (No. 8), the governor is moving up on the list more from a spate of good luck than his own machinations. His formidable primary challengers have all but disappeared from the governor’s race. His suspension of legislators’ pay to push pension reform … Read more

Ken Griffin

28 Ken Griffin Age: 45 Occupation: Founder and CEO, Citadel Investments Considered the richest man in Chicago (Forbes estimates his wealth at $4.4 billion), this conservative hedge fund founder—who with his wife, Anne, is a big donor to health and education causes—commands attention when he speaks. But he doesn’t always hew to the party line. In … Read more

Fred Eychaner

32 Fred Eychaner Age: 69 Occupation: CEO, Newsweb Corp. Illinois legislators Heather Steans and Greg Harris introduced the bill, and Mike Madigan (No. 2) delivered the 13 swing votes. But one of the most important backers of the same-sex marriage campaign was this reclusive printing company owner, who reminds us yet again that money absolutely influences … Read more

Bruce Rauner

37 Bruce Rauner Age: 58 Occupation: GOP candidate for governor Rauner’s spot on this list has reached its inevitable crossroads: If he wins the GOP primary and defeats Governor Quinn in November, he will serve as the political counterweight to Democrats Madigan and Emanuel. Should he lose, he may fall off the list altogether. Despite … Read more

Karen Lewis

40 Karen Lewis Age: 60 Occupation: President, Chicago Teachers Union The union leader was powerless against the massive teacher layoffs and the 49 school closings that roiled CPS last year. But the cred she earned during the 2012 strike has made her a potent watchdog figure on an issue that virtually everyone cares about. Photo: … Read more