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

Lori Healey

If all had gone according to plan, Healey would be scrambling right now to get Chicago in tiptop shape to host the Summer Olympics. Instead, as head of McPier since April, she’s scrambling to keep tourists and conventioneers coming to the city. The headwinds are strong, including $3.5 billion in bond debt, flat hotel occupancy, … Read more

Stefan Edlis and Gael Neeson

The future of the Art Institute of Chicago is in plastics. That is, plastics mogul Stefan Edlis and his wife, Gael Neeson, who last April donated 44 works of pop art valued at $400 million—the biggest gift in the museum’s history. While a $35 million cash gift from the late Dorothy Braude Edinburg made news … 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

Howard Tullman

Calling it 1871 3.0, this serial entrepreneur led the Merchandise Mart–based tech hub in yet another expansion—and to a No. 1 ranking (from a Swedish research firm that studies tech centers) as the nation’s best university-affiliated incubator. Power Quote “Whatever was yesterday’s miracle is tomorrow’s ‘So what?’ ”

Sam Toia

Chefs and restaurateurs grab most of the attention, but this politically connected, under-the-radar power broker is the engine driving Chicago’s thriving foodie industry. Last year was a four-star one for Toia: He successfully lobbied to bring back happy hour in Illinois (multiple attempts since the late ’80s had failed); helped restore state funding to Choose … Read more

Susana Mendoza

Look above: You’re staring at the future of the Democratic Party in Illinois. The daughter of Mexican immigrants, Mendoza was only 28 when she was elected to the statehouse. Last May, she was sworn in for her second term as city clerk. Now she’s stepping up to run statewide in the November special election for … 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

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.