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This study explores one of Tibet's greatest thinkers, Longchenpa (1308-1364), within the context of the `rhetoric of negation', an intense critique of philosophical views and spiritual practices that displays their inability to lead directly to liberation. Like that of his predecessors, Longchenpa's rhetoric of negation aimed to dismantle compulsive conceptualising mental processes, which creates an absence. However, Longchenpa went one step further and overcame the futile liberation of spiritual practices by creatively transforming his rhetoric of negation into a pedagogy capable of facilitating the experience of natural awareness, or liberation. The book attempts to trace and reveal Longchenpa's transformation from negation into an experience of natural awareness, and then explore whether such transformation is compatible with the Two Truths doctrine and Dzogchen's notion of non-duality. Such an inquiry also has broader implications for any method applied within a non-dual soteriological system. The study also emphasizes Longchenpa's role as a teacher of liberation, which has not been explored in academic research of his texts. Additionally, it contextualizes him biographically and historically. The contextualization "humanizes" and depicts a "realistic" portrait of Longchenpa, and determines his position in the Tibetan realities of his time, questioning whether it had any implications that shaped his 'rhetoric of negation'.