This thesis examines the life of Ngaati Tiipa rangatira Waata Kukutai (1822-1867), and critiques historical perspectives that have narrowly identified him as merely a Kuupapa loyalist. This study argues that Kukutai’s choices and leadership were driven first and foremost by those things he viewed as crucial to Ngaati Tiipa autonomy and wellbeing. Kukutai was an articulate and well-educated leader of Ngaati Tiipa. Waata was governed by principles of rangatiratanga (chieftainship), mana motuhake (independence) and loyalty to Ngaati Tiipa and to the whenua. He was deeply religious and courageous and was an entrepreneur who sought to protect his people by securing economic independence. This thesis shows how he negotiated colonial structures by forming strategic alliances, and in the process led his people through one of the most turbulent periods in New Zealand history. Waata was an enigma shaped by loss, vision and hope for a new future in extraordinary times in New Zealand’s history. Waata was a polarising personality who held fast to his life principles. He withstood immense pressure from other Waikato chiefs during the Waikato invasion. During the Waikato War Waata was most active, carrying letters, food and supplies to colonial soldiers and earned himself and his tribe of Ngaati Tiipa the label of kuupapa. While Waata was not the only ‘friendly chief’ during colonial times he has been the most pillorised in Waikato. Seemingly ignored by many historians is at the same time Waata ensued that Ngaati Tiipa land was never invaded by the colonial troops. Waata’s actions protected his people and his land and maintained his mana motuhake, his sovereignty over his district.