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Within the context of a large urban school district in the southeastern United States, we examined: (a) the factor structure of scores from a new measure of administrators’ preferred teacher applicant characteristics, and (b) the relationships between administrator demographics and their preferred applicant characteristics. A four-factor structure was identified (Personal, Professional, Student Outcomes, Demographics) and less preference for professional characteristics, which have been identified as showing the most promising associations with student achievement gains by research and targeted by policies to improve teacher quality. We found a significant difference between principals and assistant principals for the demographics of teacher applicants. This may result from principals feeling greater pressure from district mandates to hire diverse staff than assistant principals.