Kiai and Pesantren are two things that cannot be separated. The character of the Kiai determines the culture of the Pesantren which at the same time forms the character of the existing santri. This article aims to find and reconstruct the actualization of kiai's collective-transformational leadership in shaping the organizational culture of the Pesantren. This research uses a qualitative approach with a multi-case study type. Retrieval of data in this study using snowball sampling. Data collection in this study used three techniques, namely: in-depth interviews; participant observation; and document analysis. Data analysis was carried out in two stages: single-case and cross-case analysis. Cross-case data analysis is intended as a process of comparing the findings obtained from each case. The results of the study state that, first, the active role of the Kyai collectively arises due to the large needs of the Pesantren. The collective active role of the Kiai in its development gave birth to the existing Pesantren culture. Where each Pesantren is different considering that the culture of the Pesantren is not far from the character of the founder and/or Kiai. Second, the collective leadership model is a leap in the tradition of Kiai leadership in Pesantren.