CEO, Chicago Public Schools
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 latest assignment looks like his toughest: close a $500 million budget hole, convince Bruce Rauner to give hundreds of millions more, and negotiate a new contract with the teachers’ union. If he pulls all this off, Chicagoans might just give him the messiest job of all: Emanuel’s.