This retrospective study examines involvement in school bullying at all developmental stages, from elementary school to university, in relation to personality traits. Participants were 216 university students, 162 (75.0%) females and 54 (25.0%) males. The majority of the sample (88.9%) aged 18-24. Students completed the International Personality Items Pool (BFFM) and a self-report questionnaire about school bullying online. The results show that the involvement roles in personality trait A3 (don't insult) of the Agreeableness (A) scale differ significantly at all educational levels. However, trait E6 Extraversion (E) and the Conscientiousness (C) scale differ at the elementary school level, and trait N6 of the Neuroticism (N) scale varies at the middle school and N3 differs at the high school. All participants differ statistically significantly in A3, Conscientiousness scale at all educational levels. Those involved differ statistically significantly in the traits Neuroticism, C8, and C9 and in two traits of Openness (O). Throughout the course of schooling, victims showed a higher score on the Conscientiousness scale than the bullies/victims. The victims who became the bullies (victims/bullies) had a higher score on the Emotional Stability scale than the bullies who became victims (bullies/victims). About half of the participants said that the experience affected them positively and the other half negatively. Those who answered that it had a positive impact on them showed a statistically significant difference in characteristics E7 (talkativeness) and N10 (pleasant mood). The findings help inform a new perspective of anti-bullying intervention that targets personality traits in all the roles and their rotation.