John Rogers Jr.

Name someone in Chicago’s power crowd, particularly its business elites, and chances are that Rogers has placed, advised, or mentored them—including a gal named Hobson (No. 18) and a fella named Obama. He marries well too: First wife Desiree Rogers went on to be Johnson Publishing’s CEO, and ex-wife No. 2, Sharon Fairley, was just … Read more

Fred Eychaner

What is Eychaner up to? Few people seem to know—and that’s just how the wealthy radio station owner likes it. Behind the scenes, however, he’s a macher of the first order. If Hillary makes it into the White House, she’ll have this Democratic megadonor, in part, to thank.

John Cullerton

In the great mess that is Springfield, Cullerton has emerged as the voice of moderation, trying to bring together the warring speaker and governor. He has put together major compromise proposals for school funding and pension reform. Along the way, he has ticked off both Madigan and Rauner—which suggests he’s doing something right.

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

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

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

Kurt Summers Jr.

This political wunderkind—and grandson of the legendary political strategist Sam Patch—began the year walking a fine line between his boss (the mayor), his former boss (Toni Preckwinkle), and his own ambitions. A loyal soldier, Summers must have heard the growing chatter that he’d be a darn good candidate to pick up the pieces of Emanuel’s … Read more

Juan Luciano

Timing is everything. And this Argentine exec, formerly ADM’s COO, replaced Patricia Woertz just as big bets on ethanol were turning sour and oil and grain prices were poised to plunge. Since he took over (in January 2015) through January 2016, ADM’s stock fell 32.5 percent. (The S&P fell just 5.8 percent.) Luciano is now … Read more

Chancellor “Chance the Rapper” Bennett

Chicago’s biggest emcee since Kanye, Chance has been on fire lately. He released his first-ever free album on iTunes (the critically worshiped Surf , with bandmate Donnie Trumpet), headlined Pitchfork, and became the first-ever unsigned act to perform on Saturday Night Live. All the while, he used his platform (1.3 million Twitter followers and counting) to … Read more

Martin Nesbitt

Barack’s bestie, entrusted to preserve the president’s legacy, is raising the dough and ratcheting up the planning for what will be the most significant civic project in Chicago since Millennium Park: the Obama library, a potential game changer for the economically depressed South Side. If only we knew where it’ll be: Jackson Park or Washington … Read more