Singapore faces a strategic dilemma as the rise of China and the US rebalance towards the Asia-Pacific result in a competition for influence. This thesis analyzes historical case studies of the Thucydides Trap to identify aggravating and mitigating factors that resulted in outcomes of either war or no war between ruling and rising powers. It then uses these factors to develop an understanding of the possible causes of conflict between the US and China. It concludes that while a conflict is possible, it is not inevitable because a conflict is not in the interest of either country. As both countries seek to avoid a direct confrontation, the security environment in the next 10 to 20 years will instead be marked by more intense competition as China seeks regional dominance. Given this security environment, this thesis recommends a hedging strategy to safeguard and advance Singapores core national interests of survival and prosperity. A hedging strategy is optimal because it allows Singapore to benefit economically and politically from a rising China through return-maximizing policies, while mitigating the possibility that Chinas rise might not be peaceful through risk-contingency policies. To implement a hedging strategy successfully, Singapore will need to leverage its ability to influence its security environment by facilitating continued US regional presence and by drawing major powers to have a stake in the region.