Village chiefs¡¦ role has been facing great impact and challenge ever since the transition of society, development of information, raise of education level and popularity of communitarianism. Therefore, how village chiefs¡¦ legal position should be set and integrate with village officers as well as community development have been brought into discussion in recent years. While gaps do exist between current academic study and practical operation, this study centers on village chiefs¡¦ position with the case of An-Shun Li of Kaohsiung City for further study. The exploration of literature is divided into three parts: role theory, village chiefs¡¦ position and village systems, and the relationship between village chiefs and community development. Literature review, in-depth interview, and participants¡¦ observation are adopted as research methods. With the concept of status, role expectation, role conflict and role performance in role theory, the study explores the interaction between village chiefs and other connecting village officers, analyzes the problems that chiefs¡¦ encounter under current legal system and then generalizes the role current chiefs should play. The research finds that the biggest difference between current and traditional chiefs is that the role they play as citizens¡¦ participation navigators and community development managers. While government is examining and adjusting village controlling area and government-assigned chief policy, it is advised that concrete solution to be proposed for individual cases which require specific environment. The regulation of village chiefs is wished to become better in the future. A new organization is looking forward to be setting up as a mediator between village chief and community development organization to deal with community affairs, thus to make the local system in line with modern society demands.