The aim of this article is to present study results concerning the structure of teacher Machiavellianism. Machiavellianism was researched extensively throughout the last 40 years as a personality feature comprising traits related to leadership manipulation tactics. Psychology describes Machiavellianism as a part of the universal model called “the dark triad of personality” alongside with subclinical narcissism, subclinical psychopathy and low empathy. The teacher Machiavellianism model presented in this article, as opposed to the universal models, strongly accentuates the context-specific variables related to the organization of life in a school, alongside with personality variables. To achieve a new insight into the mechanism of how teacher Machiavellianism is generated, structural equation modeling (SEM) was used, which incorporates personality variables such as: self-effi cacy, disposition for gratitude, values, one’s personal resources, professional burnout, alongside context-specific variables like: organizational culture, work attitude, tenure and specialization in the tasks performed. Results of two studies are shown, discussing the empirical structure of teacher Machiavellianism components in relation to the initial theoretical model.