This chapter examines why India emerged as a stable democracy after independence, while Pakistan experienced recurring authoritarian rule. While both countries inherited similar colonial institutions from British rule, they nonetheless diverged considerably as political entities in the post-independence phase due to differences in the organizational strength of the political parties, the character of leadership, and the process of partition itself. In India, the Indian National Congress, through its grassroots organization and mass movements under the leadership of Gandhi and Nehru, succeeded in building legitimacy and a stable political rule that supported democratic consolidation. In contrast, Pakistan’s Muslim League lacked strong party organization and early on lost the charismatic leadership of Jinnah soon after independence, leading to an unstable rule which produced a context for a military coup d’état. The British decision to partition India and Pakistan in 1947—amid escalating communal riots—in fact, proved hasty and ended up imposing heavy political burden and caused national integration in both countries to become challenging, especially on Pakistan which was divided between its Western half and the Eastern zone (that became contemporary Bangladesh in 1971) and separated by a distance of almost 2,000 km. These structural and institutional fragilities, combined with the unequal dominance of West Pakistan and military influence, undermined democratic potential in Pakistan. This chapter argues that the interaction of actors and institutions during the decolonization process—especially Britain’s reckless choices—critically shaped the contrasting post-colonial political regimes in India and Pakistan.