Utilizing rich data on nearly 11,000 educators over 17 academic years in a highly diverse context, we examine the career paths of teachers to determine whether and when they transition into the principalship. We utilize a variety of event history analyses, including discrete-time hazard modeling, to determine how an individual's race, gender, and their combination--among other characteristics--contribute to their likelihood of making this transition. We found that inequitable pathways to the principalship are not explained by systematic differences in personal and contextual characteristics along lines of race and gender but rather that the selection of school leaders may be a process influenced by systemic bias.