In regions riddled with heightened security tensions from great power competition like Southeast Asia, why do states like the Philippines defy conventional rationality and hedge against great powers? This paper seeks to answer this anomaly by going against the literature of hedging to propose the theory of Offensive Hedging, arguing for an offensive realist reconsideration of Philippine Grand Strategy. Supplementing this theory, this paper will redefine hedging as a grand strategy to account for anomalous cases that exist across the literature. These arguments will be supported by analyzing Sino-Philippine partnerships through numerous lenses during the height of Philippine Hedging (2016-2022) and correlate such practices with maritime stand-offs between the two nations in the West Philippine Sea.