Einstein said that darkness is absence of light. It is assumed that absence of leadership or misappropriation of leadership characteristics and behaviors results in Dark leadership, and it is the system that produces a culture in which dark side of leadership becomes acceptable. In this chapter, I would be exploring the role of middle leadership (school heads, district education officers, and administrative officers) of school education department in Punjab. The chapter is based upon a qualitative study with in-service school teachers and school heads. The critical incident technique was used to collect data, and interpretive analysis was used to interpret data at various levels from coding to themes generation and interpretation of the phenomenon, dark side of leadership. Goleman's Dark Triad comprising, authoritarian, narcissistic, and psychopathic, provide theoretical basis of the analysis. The results are shared in a story form progressively supplemented with the evidence generating discourse about the dark side of leadership in the educational settings of Punjab. The study acts like a mirror shedding lights into the deep and dark corners of leadership making them aware of their creepy existence and challenging them to create meaningful acceptance for themselves by coming into light and leaving the dark behind.