This article examines the development of Islamic legal theory during the leadership of Umar bin Khattab, focusing on his leadership model, social setting, and the practice of ijtihad in responding to the dynamics of early Islamic society. The study aims to analyze how Umar bin Khattab applied Islamic law contextually without departing from the fundamental principles of the Qur'an and Sunnah. This research employs a qualitative method with a library research approach by analyzing primary and secondary sources related to the history of Islamic legal thought. The findings indicate that Umar bin Khattab's leadership played a crucial role in shaping an adaptive, just, and maslahah-oriented Islamic legal system. His ijtihad, such as the suspension of zakat distribution for muallaf and the postponement of hudud punishments during periods of social crisis, reflects a progressive understanding of Islamic law that prioritizes justice and public welfare. These legal policies demonstrate that Islamic law during Umar's era was not merely normative, but also practical and responsive to social, political, and economic challenges. This study concludes that Umar bin Khattab's approach to ijtihad serves as an important foundation for the development of contextual and dynamic Islamic legal thought that remains relevant across different times and circumstances
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