Persistent bullying behavior is that which starts high and remains either moderately high or persistently high, seemingly in spite of intervention/prevention approaches employed: yet little is known about how/why persistent bullying emerges or is sustained. Those who do not respond to interventions and persist with their bullying behavior, require close consideration and more targeted, nuanced approaches. This instrumental case-study uniquely explores a self-identified, high-persistent bully's explanations of how the bullying emerged, and what supported/sustained it to become a persistent behavior. A whole-of-life interview protocol facilitated a reflective exploration of the participant's social and behavioral 'turning points': the influence of transitions and changes in one's life: serving to initially steer him toward bullying others, and eventually sustaining his persistent bullying behavior over time. An interpretative phenomenological analysis (IPA) revealed three 'turning points' which seemingly met his primary personal and social goals/needs of belonging, social positioning and status. This paper adds to the literature by introducing the notion of 'turning points' as a possible mechanism that facilitates the emergence of, and sustains persistent negative/bullying behaviors. Understanding turning points and any chain reactions in the lives of those who engage in higher, persistent levels of bullying can inform the development of future measures, intervention approaches and provide insights into issues of care for individuals engaging in persistent bullying.