A tiny city-state, Singapore has perceived its vulnerability as rooted in its miniscule size, limited resources, and geopolitical setting. Not directly involved in the competition between great powers, Singapore has hedged between the dominant powers of the Indo-Pacific for survival. This article introduces the concept of principled hedging, as opposed to desultory or indiscriminate hedging. It adds that Singapore’s role of mediator, which counterintuitively challenges its hedging strategy by involving itself in regional and great-power geopolitics and taking sides based on the key principles of non-interventionism and observance of international law, allows Singapore to carve out for itself maximum space in diplomacy and geopolitics. Singapore also mediates between great powers and pursues the role of international middleperson and host of high-profile summits to assert its identity, not only for branding and public diplomacy but also for pushing China and the United States to reach a kind of détente so that it does not have to take sides explicitly. Singapore strictly adheres to the principles of non-interventionism and observance of international law, developing not only a collective position through the Association of Southeast Asian Nations (ASEAN) but also an independent role of mediator between China and the United States. By playing the role of mediator, Singapore has projected an image of impartiality, pragmatism, and rationality that plays into the strategic considerations of great powers and offers opportunities for independent policymaking and self-expression of geopolitical views.