This chapter seeks to situate the League in a political developmental context to deepen understandings of the institution's place in history and its enduring relevance today. It examines the origins of the League of Nations, highlighting the institutional precursors that helped provide the League's ideational foundations. The chapter draws on the concept of legitimacy to analyze the League's troubled existence during the interwar years. The League was widely delegitimated in terms of substance and process, which contributed to its failure and the naїve utopianism that it would come to symbolize. The chapter therefore concludes with a discussion of how situating the League in time helps recover some of the deeper significance of the League experience and needles the thread. The flaws of the League were temporally and historically contingent, as it reflected a direct and pragmatic byproduct of the political moment of time in which it was conceived. The resulting bargain thus embodied a significant degree of hypocrisy.