This study aims to determine the relationships between leadership style, job satisfaction, and organizational commitment within the context of a pesantren in Indonesia. In specific, there were five research objectives. First, to determine the level of charismatic, transformational, and autocratic leadership styles among the Kyai. Second, to examine the effects of charismatic, transformational, and autocratic leadership styles on job satisfaction. Third, to examine the effects of charismatic, transformational, and autocratic leadership styles on organizational commitment. Fourth, to examine the effect of job satisfaction on organizational commitment. Fifth, to assess the mediating role of job satisfaction between charismatic, transformation, and autocratic leadership styles with organizational commitment. The quantitative methodology and correlational research design was employed. Research data were collected through a questionnaire from 556 educators from four branches of Pesantren Darunnajah, Indonesia. Respondents were selected using the cluster sampling technique. The questionnaire was developed based on the previously established scales. The data were analyzed using multiple regression analysis to test the hypotheses. Hierarchical regression analysis was applied to test the mediation hypotheses. It was found that there was a significant relationship between charismatic leadership (β: 0.112, t: 4.318), transformational leadership (β: 0.753, t: 28.012), autocratic leadership (β: 0.082, t: 3.314) and organizational commitment. Charismatic leadership (β: 0.104, t: 4.275), transformational leadership (β: 0.769, t: 30.601), and autocratic leadership (β: 0.112; t: 4.832) also had significant relationships with job satisfaction. In addition, job satisfaction had a significant relationship with organizational commitment. Finally, job satisfaction mediated between charismatic leadership, transformational leadership, and autocratic leadership with organizational commitment. This study extends the literature about the relationships between charismatic, transformational, and autocratic leadership styles with job satisfaction and organizational commitment in the context of pesantren in Indonesia. It also contributes empirical evidence on the role of job satisfaction as a mediator in the relationships.