Fifty-two years after Brown v. Board of Education and 42 years after the Civil Rights Act of 1964, there remains a declining presence of Black teachers and administrators in the United States. As powerful role models for all students, especially Black students, Black educators are crucial to the increasing minority student population (First Minority Awareness Summit, 2004). This study investigated the factors that influence Black teachers with respect to applying for and accepting the principalship and identified the factors relative to this dilemma. A historical review was presented to convey how Black teachers and administrators have arrived at their present circumstances. This historical review was enhanced by an understanding of why Black teachers choose to become principals; therefore, job choice theory, including subjective, objective, work itself, school context, and critical contact factors, was explained. Through the use of survey methods, 325 participants' responses to the Principal Job Survey (Barksdale, 2003) from 10 public school divisions in Region II, Region III, and Region IV in Virginia were analyzed. Hierarchical multiple regression and descriptive statistics were utilized to analyze 65 attributes on the survey, as measured on a 5-point rating scale. The five independent (predictor) variables were objective, subjective, critical contact, school context, and work itself job choice theory factors. The dependent (criterion) variables were identified as job desirability index and overall attractiveness of the principalship, as well as the probability of seeking, being offered, and accepting the principalship. The findings determined that work itself was the predictive factor in an individual's applying for or accepting the principalship with regard to all five dependent variables. Only for the dependent variable of overall attractiveness were subjective, critical contact, and work itself factors predictive of Black teachers' seeking the principalship.