Principals play an important role in determining the quality of their schools by the selection of teachers. A preponderance of evidence from the economic and education policy literature indicates that teachers with stronger academic backgrounds produce better student outcomes. This article hypothesizes that school principals with certain attributes are likely to favor teachers with similar attributes to their own. This study uses the Schools and Staffing Surveys from 1993 to 1994 to test whether school administrators who attended more selective universities are more or less likely to hire teachers who attended more selective undergraduate institutions. Findings suggest that principals undergraduate background matters when it comes to their recruitment, selection, and perhaps retention of teachers with strong academic undergraduate backgrounds, especially in high-poverty schools. Principals in high-poverty schools who attended highly or the most selective undergraduate institutions were 3.3 times more likely to hire teachers who attended similar institutions.