The Five Chicago People Central to Obama's Presidency Six years in, Michelle and Barack Obama still rely on a contingent of ex-Chicagoans. By Kaitlyn Jakola February 17, 2014, 11:20 am Valerie Jarrett 57, senior adviser The Obamas’ closest confidante has been by the presidential family’s side since she hired Michelle to work for Mayor Richard Daley in 1991. Arne Duncan 59, U.S. secretary of education The next task for this former CEO of CPS: make early childhood education a nationwide reality. Tina Tchen 58, FLOTUS chief of staff Tchen spent 13 years representing public agencies like the Chicago Housing Authority before she was appointed chief of staff in 2011. Sam Kass 33, top chef This former Avec chef leads the First Lady’s healthy foods initiative. Pete Souza 59, POTUS photog This former Trib photographer documents all the First Family’s big moments.