The transition from the Rashidi to the Umayyad caliphate signifies politically a turning point in the early Islamic history. The first Umayyad caliph, Mu‘awiya b. Abi Sufyan (r. 41-60/ 661-680), came to power after bloody civil war, remembered in Islamic sources as the first fitna. He also was the first Muslim ruler to turn caliphate into hereditary succession by ordering his governors to take the oath of allegiance (bay‘a) for his son Yazid (r. 60-64/ 680-683). Mu’awiya’s unprecedented move represented for many Muslims a rapture from traditional models of rulerlship set by previous caliphs. These political transformations deepened tensions and debates within early Islamic community regarding the question of succession and legitimate leadership. This dramatic turn of events led to the emergence of oppositional factions against the Umayyads, such as the ‘Alids, Kharijites, and the Zubayrids. The proposed paper analyzes the earliest Islamic views regarding Mu‘awiya’s decision to appoint Yazid as his successor and investigates the religio-political reactions to this move. The paper places an emphasis on the role of ‘Abd al-Rahman b. Abi Bakr (d. 58/666) in the Hijazi opposition to Mu‘awiya’s controversial move. It also evaluates the extent to which his image as an oppositional leader changes over the time and reasons behind these transformations. The paper also gives insights into some of the legitimizing strategies that Umayyads applied against their adversaries. Methodologically, the paper follows primarily a comparative textual analysis of relevant accounts presented by early Muslim authors, particularly Qur’anic exegetes, belletrists, and historians. The paper, therefore, sheds light on the role that tafsir and ?adith literature played in the evolution of early Islamic historical writing. The interaction between these literary genres will demonstrate that historical construction of events sometimes are more affected by narrative arrangement and the authors’ agenda than sources accessibility. In doing so, the study will also touch upon the problematic nature of Islamic sources for the construction of the earlier stages of Islamic history as they were not contemporaneous to the events they purport to describe.