This study explored the personal and situational factors that contribute to a high school principal's willingness to sell the issue of objectionable team nicknames to their school division administration for the purposes of banning them. Based on the literature review, nine hypotheses were developed regarding the factors that influence the issue-selling process in a centralized, hierarchical organization. The issue-selling model utilized in this study suggested that organizational support, top management openness, organizational norms, probability of success, and image risk would be determinants of willingness to sell the issue (Mullen, 2005). This study utilized a mixed-method research design. Personal interviews were conducted with retired and current high school principals that had dealt with the objectionable team nicknames during their careers. In addition, questionnaires were electronically sent to 311 current high school principals. Ordinary least squares regression identified perceived probability of success and image risk to be the factors that have the most statistical impact on a high school principal's willingness to sell the objectionable team nickname to their superior. Logistic regression was used to determine the likelihood that an emotional issue would be brought forth. This study provides recommendations concerning issue selling in a public school system.