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Scholars note that teachers of color (TOC) not only serve as role models who share the same race/ethnicity but also offer valuable perspectives to all students. However, the proportion of TOC has remained stagnant for decades while the number of students of color has increased rapidly. We use statewide longitudinal application data in Wisconsin. First, we examine the relationship between school-level characteristics and the size of the TOC application pool. Second, we examine the extent to which TOC are more or less likely to apply to a school with a principal of the same race. Lastly, we examine the extent to which TOC are more or less likely to be hired at a school with a principal of the same race.