Trusting relationships play a crucial role in all aspects of school life. This study builds on this understanding by exploring the role gender and race/ethnicity plays in establishing trust between teachers and principals. Utilizing statewide working conditions survey administered in North Carolina, we employ both descriptive and analytic methods to examine the relationship between the racial/ethnic and gender match between teachers and principals and teachers' trust in their principal. Our analyses indicate that race matters in establishing trust between teachers and principals. We suggest implications for educational leaders and principal preparation programs.