While ‘winning’ might be considered a fundamental part of the human objective, what constitutes winning and how one might achieve it remain somewhat abstract, in war as in any other human endeavor. ‘Winning’ militarily at the tactical level – in a firefight or a battle – has always been more quantifiable than at the strategic level. At the strategic level, success might be measured by means of three big ideas: ownership; intervention for effect; and fighting for ideas. The divergence between success at the tactical level and the political context of the war creates a challenge at the operational level when it relates to political and strategic matters.The result of a research project carried out by the Centre for Historical Analysis and Conflict Research for the British Army, this book analyses the philosophical constituents of what may comprise ‘victory’ or ‘winning’ and then travels, chronologically, through a wide set of historical case studies, exploring those more philosophical components and weaving them into the factual discussion. Thus the factual relation and analysis is the vehicle for a deeper exploration of the concept of success or ‘winning’, rather than a narrative end in itself.