This field research seeks to analyze various developments and changes in the world of pesantren in the midst of changing societies and dynamic national political struggles. The kiai and pesantren institutions in the Indonesian context and the northern Javanese pesisiran in particular have various strategic roles both in the religious education sector which also guides the views and behavior of the surrounding community. In this research, it is seen from a socio-anthropological perspective with a choice of qualitative approaches. The data were collected through the observation by staying at the research location for several months, as well as interviewing the kiai, asaatidz, teachers at the pesantren, as well as several community leaders. Some historical data and others were obtained through documentation and search of other related literature. The findings of this study include the first presence of kiai with pesantren in northern coastal (pesisiran) Pati of Central Java, which has made many transformative social contributions to the surrounding environment. Both, historically, the pioneering of da'wah and the transformation of the pesantren, have been initiated by the kiai since the era of the struggle for independence, from kiai Salam, kiai Mahfudz to kiai Sahal struggle era and the young kiai in Islamic boarding schools in the Pati region, the northern coast of Java. The three Islamic boarding schools with social capital owned by the kiai (in the form of networking, norms, and trusts) not only play a role in interpreting and dialoguing the traditional values of Islamic teachings, but also maintaining and providing a role model for moderate Islam, in the empowerment movement of socio-religious, socio-education and socio-economics, even the socio-politics of contemporary society.