The study examined the possible roles that creativity plays in students dropping out of high school. It used data from the National Educational Longitudinal Study (NELS: 88), the Educational Longitudinal Study (ELS: 2002), and 87 high school students from a low income area in southeastern Michigan. NELS and ELS questions related to creative personality and anticreative school environment were selected and asked of students. The students' responses were compared to their scores on measures of creativity (Runco Ideational Behavior Scale, Torrance Tests of Creative Thinking, & Scales for Rating the Behavioral Characteristics of Superior Students). The NELS respondents who showed creative personality were identified and examined whether their creativity related to dropping out. The results of logistic regression analyses indicated that the questions selected from NELS and ELS that showed anticreative school environment have a negative correlation with the scores on the creativity measures, which affect students' dropping out. An understanding of these students and their behavior will help promote creative students' academic and lifelong success through appropriate classroom restructuring.