This work is an intervention in the historiography of the sixteenth and seventeenth centuries Orissa in the complex intersection between the State, legitimacy, and society. An analysis has been made of the endogenous and exogenous circumstances related to the formation of the State, the social structure, cultural identity, and political framework ofthe State of Sambalpur in the western part of Orissa and the State of Khurda in the coastal part of Orissa. In its essence, this book shows the complex patterns of state formation and multiple processes of the legitimacy of Sambalpur and Khurda. As a result, the states emerged as regional powers in the two geopolitical regions of Medieval Orissa. It is hoped that this intervention will be judged adequate by readers Dr. Brundaban Mishra, currently working as an Associate Professor in the School of Liberal Arts & Humanities, Woxsen University, Hyderabad, India. Dr. Mishra did Postdoc [JSPS Fellow] from Kyoto University, Japan, in South Asian History andobtained Ph. D from Jawaharlal Nehru University, New Delhi, in Indian History. He worked as a Senior Research Associate at the Global Institute for Tomorrow, Hong Kong, a Research Associate at Centre de Sciences Humanies [French Ministry of Foreign Affairs, New Delhi], and the Department of Culture Government of India.