Even before Mayor Emanuel tapped him to lead the city’s school board in 2011, this one-time head of the Chicago Board of Trade had insider cred: He was the behind-the-scenes budgetary guru for wunderkind CPS chief Arne Duncan from 2003 to 2006. Vitale emerged in the public eye last year during CPS negotiations with Karen Lewis (No. 24). He played the adult in the room. And got that contract signed.

Photograph: BOB STEFKO