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Forrest Claypool

Claypool stars in the political equivalent of that old Mike Rowe show Dirty Jobs: He’s the guy who’s always called on to clean up someone else’s mess. Patronage at the Chicago Park District. The Ventra rollout debacle at the CTA. All manner of trouble on the Fifth Floor as Rahm’s third chief of staff. Claypool’s … Read more

David Reifman

Though hardly a household name, this heavy-hitting zoning guru has repped some of the biggest real estate developers on some of Chicago’s most transformative projects in recent years, including counseling the Cubs on the Wrigley Field rebuild and winning approval for the Ryerson steel redevelopment in Pullman. When the mayor plucked Reifman in September for … Read more

Toni Preckwinkle

The Cook County Democrats’ No. 2 chieftain—a “tweedy independent with sensible shoes,” as the Tribune’s John Kass once described her—more powerful than Chicago mayor Rahm Emanuel? Right now, absolutely. Long known as a workhorse and policy wonk who appeals to lakefront liberal types, Preckwinkle recently unleashed her Machiavellian side. While much of Rahm’s credibility and … Read more

Dennis Muilenburg

He may be new to the corner office (as of July), but not to Boeing: Muilenburg started working at the aerospace giant as an engineering intern back in 1985. So far, he’s had a few wins (for example, reaching a union contract deal) and a few stumbles (Boeing stock fell 15 percent in the January … Read more

Paul Kahan

At this point, the question is not whether you’ll find yourself at a critically acclaimed Kahan joint, but which one. Big Star, Dove’s Luncheonette, or the Violet Hour in Wicker Park? Or maybe Avec, Blackbird, or the Publican in the West Loop? Add in a still-under-wraps showpiece slated for the intersection of Damen, North, and … Read more

Michael Ferro

In February, this controversial, well-connected tech entrepreneur (and part owner of the Sun-Times) became chairman and top shareholder of Tribune Publishing, Chicago’s parent—vaulting Ferro onto the national media stage. For better or worse, the fate of print journalism in this town rests largely in his hands.

Rahm Emanuel

It stinks to be Rahm right now. Check out the spectacular free fall in his public approval ratings, particularly since the release in November of the Laquan McDonald video. But the downward trend—which bobbed up a bit at presstime—began well before then. Witness his tougher-than-expected reelection last spring, when he donned a fuzzy sweater and … Read more

Mellody Hobson

Don’t call her George Lucas’s wife. The only Chicagoan to land on Time magazine’s 2015 list of the 100 most influential people—alongside the likes of Apple CEO Tim Cook and the infamous Koch brothers—Hobson is, of course, a major power in corporate America: She’s president of Ariel Investments and on several blue-chip boards (Starbucks, Estée … Read more

Robert Zimmer

In many respects, Zimmer had a terrific year: The university won the Obama presidential library sweepstakes, for example, and U. of C. Medicine announced that it would open a badly needed Level I trauma care center, a move applauded by virtually the entire South Side. Numbers, however, may be catching up to this trained mathematician. … Read more

Curtis Duffy

The owner of Grace—one of only three Chicago restaurants to ever earn three Michelin stars—can command $940 for a nine-course dinner for two with wine pairings and still pack the seats. Duffy’s fame extended further this year: For Grace, a documentary about him, garnered impressive buzz on the festival circuit.