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Education research to date has largely ignored the principal’s role in teacher hiring (Engel & Finch, 2015). This reality is unnerving as teachers are the most important school-level factor in student learning (e.g., Rockoff, 2004; Rivkin, Hanushek, & Kain, 2005) and thus hiring quality teachers is a critical component of school success and improving equality of educational opportunity for all students (Hallinger & Heck, 1998; Horng, Klasik, & Loeb, 2010). This comparative case study aims to provide a better understanding of teacher hiring practices and subsequent fit in three high schools with divergent performance, socioeconomic, and racial/ethnic characteristics located within the same mid-sized city school district.