This chapter examines the entrenchment of caste-based moral and legal codes that essentially favoured Brahmanical power in the region of Malabar on the southwestern coast of the Indian subcontinent over a longue durée period from twelfth to the early nineteenth centuries. The agrarian expansion in medieval Kerala (of which Malabar was a part) favoured a hierarchical structure that placed the Brahmans at the top of the societal ladder. This cultural power gave them the legitimacy to arbitrate on various caste-based moral and legal codes known as maryadas. This was also accompanied by a process of a decentralised system of administration. But this was temporarily unsettled with the coming of some Mysore rulers who designed a centralised administrative force modelled on the idea of political sovereignty in the second half of the eighteenth century. Under this structure, the opponents of the rulers were not spared as they were inflicted with severe punishments. Subsequently, the Brahmans and the other dominant caste landholders fled from the northern part of Kerala known as Malabar to Travancore region in the south. However, the defeat of the then Mysore Ruler Tipu Sultan in the last decade of the eighteenth century, followed by the onset of English colonial rule, reinstated cultural and land privileges for the Brahmins and other dominant caste landholders who had since returned to the Malabar region. The elemental collaboration between the English colonial state and the landed Brahmans also resulted in the re-sanctioning of maryadas within the newly established legal system of the former in Malabar. One of its manifestations could be seen through the appointment of Nambudiri Brahmans and Pandits as arbitrators in deciding judicial verdicts under the colonial legal system. Against this historical backdrop, this chapter offers a critical exploration of some early correspondences exchanged between some chieftains of Malabar and the English East India Company that would illuminate how the socio-cultural aspects of power were codified into the colonial legal system, by extension, its authority.