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Llywelyn ab Iorwerth (1173-1140) has long been considered one of the leading heroes of Wales. The life and rule of Llywelyn, known as Llywelyn the Great, is explored in detail in this thesis. The grandson of Owain Gwynedd, ruler of North Wales from 1137-1170, Llywelyn grew up during the period of turmoil following Owain’s death. After wresting control of Gwynedd from his rival family members in the latter decade of the 12th century, he proceeded to gain recognition as the foremost representative of Wales on the political stage. Although viewed as a legendary hero in Welsh history, poetry and culture, Llywelyn's route to power is more complex than that. The thesis explores the development of the man from rebel and warlord, to leader and spokesman, to statesman, traces the expansion of his hegemony throughout Wales, and discusses the methods he used to gain and maintain power. Particular attention is paid to his use of family, marriage, allies, rivals and the church to achieve his goals. These insights can be derived from the surviving charters, letters, and other acta of Llywelyn and the Royal Chancery of England, the titles accorded therein, Welsh and English chronicles, as well as, occasionally, Venedotian Poetry. Finally, this thesis seeks to address the limitations on Llywelyn’s successes, in light of succeeding events and concludes with a discussion of Llywelyn’s legendary status in the modern world.