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The thesis explores the concept of grand strategy and applies it to the development of Taiwan’s grand strategy between 1949 and 2008, from Presidents Chiang Kai-shek, Chiang Ching-kuo and Lee Teng-hui to Chen Shui-bian. The thesis first examines the debates between the ‘classical’ war-centred and ‘neo-classical’ peace-centred perspectives in the realm of strategic studies and argues that these need not be mutually exclusive, but can in fact supplement one another. The thesis then adopts a stance of theoretical pluralism, whereby grand strategy is regarded as a process of power practice across periods of war and peace; it defines grand strategy as a cognitive state agent taking action to create and manipulate power in furthering its desired ends in a dynamic international society. This convergent perspective of grand strategy is designed to embrace these two schools of thought, since it is equally important for those who seek a better understanding of grand strategy in general and the evolution of Taiwan’s grand strategy in particular to focus both on how best to wage war and how best to preserve peace. To make sense of and to apply the concept of grand strategy, as an operational term, this thesis proposes four strategic analytical dimensions, namely, capability, choice, environment and posture, which are informed by the duality of four analytical pairs: ideational and material factors, ends and means, agency and structure, and defence and offence. Building upon this strategic analytical framework, the thesis moves to explore the perspective of leadership in Taipei against the backdrop of the politicalmilitary confrontation between the ROC on Taiwan and the PRC. The thesis investigates how and how far Taiwan’s grand strategy had been conditioned and developed by the influence of the Taipei-Beijing competition for sovereignty, changes in the international context, the unique strategic perspective of the successive presidents, domestic political developments and the asymmetry of national power between Taiwan and China. Through its investigation, the thesis argues that Taiwan’s grand strategy over the past six decades has been fundamentally driven by one prime factor: to secure the perspective of the ROC’s sovereign status as understood by Taipei’s leaders, not only across the Strait but also in international society.