This paper aims to examine the best leadership approach for law enforcement managers and supervisors. To address this issue, we will examine the leadership phenomenon and a case study in a police department. Thus, we can provide a frame work which includes the pertinent aspects of the leadership theories and their applicability to the criminal justice organizations. This study will also review several leadership models of leadership and discuss their applicability to the law enforcement organizations. Then we identified three challenges that hinder the leadership process in law enforcement agencies which are political affiliation, shifting structure of law enforcement organizations, and lack of delegation.