Bullying is a phenomenon that is as old as childhood itself. It has existed for decades. The concept of bullying is problematic because of the myriad ways educational leaders and students define and characterize it. The purpose of this study was to explore the relationship between bullying and gender and the relationship between bullying and school leadership within two divergent school environments, that is, two public schools and one private school. The questions that guided this study involved bullying and gender, bullying and bullying behaviors, and bullying and leadership. The research study used a mixed method approach, a correlational design which used a survey to explore bullying and gender and interview data for bullying and leadership. The survey instrument used to gather the student data was the Olweus Bully/Victim Questionnaire; the administrative data was gathered using the Background Questionnaire and the Interview Questionnaire, both created by Dr. Phillip Jackson, Jr. The population was students that attended schools in an urban school district in Southeast Georgia; there were approximately 100 students randomly sampled from each school.