The firm Sacks runs—which invests in hedge funds on behalf of big clients such as pension funds and endowments—may help determine how cushy your retirement is. He is also thisclose to Rahm, who handpicked him to be the city’s corporate ambassador at World Business Chicago. No one outside the administration appears on the mayor’s schedule more than Sacks, the Chicago Tribune reported. “If we had a commerce secretary,” says a City Hall insider, “it’d be Michael.”

Photograph: RAMZI DREESSEN