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In the past few years, especially after the 2008 global financial crisis, China has become more assertive, not just in its military posture but also in its diplomatic affairs and economic interactions. Despite this rising assertiveness, China’s grand strategy officially remains that of ‘Peaceful Development.’ In consequence, scholars have disagreed about the trajectory of China’s grand strategy in light of its often ambivalent behavior. To explain this ambivalence, this article will take a closer empirical look at two important developments regarding China’s international affairs: The softening on China’s preoccupation with territorial integrity and sovereignty has been exhibited in taking sides with Russia in the Ukraine Crisis, as well as its continually increasing participation in United Nations peacekeeping missions. In contrast to more common materialist explanations, this article argues that the ambivalence of these actions can best be explained by contextualizing them with China’s history and sense of legitimacy.