Chancelor Jonathan Bennett was born in Chicago, Illinois. His father, Ken Williams-Bennett, was an aide to the late Chicago mayor Harold Washington and then-Senator Barack Obama. His mother, Lisa Bennett, worked for the Illinois Attorney General. Bennett grew up in the middle-class neighborhood of West Chatham on Chicago's South Side. When Bennett was sixteen, his father began to work in the Department of Labor during President Barack Obama's first term. Bennett personally met President Obama in his youth and discussed his aspirations to be a rapper, to which Obama responded with "word". Bennett was originally going to move to Washington, D. C. following Obama's win in the 2008 presidential election, though those plans eventually fell through. Bennett attended Jones College Prep High School where he was a member of the Jewish Student Union.