The research in this brief takes place within the context of efforts to strengthen the principalship in Chicago Public Schools (CPS). Using eight years of data from CPS, 2012-13 to 2019-20, this brief describes Chicago's principals--their demographic characteristics, their backgrounds, their trajectories into the principalship, and how long they stay. The authors focus intentionally on the racial/ethnic diversity of the principalship since CPS is a district that primarily serves Black and brown students. In addition, this brief describes how their previous experiences in schools align with the schools they ultimately lead. The brief concludes by looking at exit rates among principals.