In the winter of 1998-99, the inexplicable presence of Pakistani troops under the pretext of being local freedom fighters in the Indian-administered side of Kashmir brought the region to the brink of a nuclear war. This paper probes the military rationale behind Pakistan’s initiative, organizational interests, internal politicking among different state organs, and the role of a few powerful individuals in the operation. It takes into account the important dimensions of strategy employed during the preparations for the Kargil War and the errors on the part of Pakistani planners which if addressed could have reversed the outcome of the operation. The controversies surrounding the Kargil conflict are discussed through the works of academicians and memoirs of the military commanders from India and Pakistan. The first part of the paper focuses on the rivalry and causes of the outbreak of war between India and Pakistan by explaining the beliefs and psychology of the military planners based on the premise of Cashman and Robinson. The second part reviews the political and nuclear milieu in which the conflict took place, while the third part accounts for the international efforts to prevent the conflict from escalating. The fourth part draws conclusions from the entire episode, indicating the discrepancies on both sides and the evidence that Kargil was unique because it challenged the military logics.