Deconstruction and destruction tend to be viewed as a continuum, on the assumption that to deconstruct is to destroy. Deconstruction certainly seems intent on the death of definitive meaning, absolute truth, theoretical flights, and universal values. Versions of the deconstructive task have been addressed and applied by philosophers throughout history and across cultures. By examining such approaches we may learn whether deconstruction must bring destruction in its wake, or whether another outcome might be possible. To test this hypothesis the philosophy of Zhuang Zi is compared with that of Friedrich Nietzsche. Their unique approaches to the deconstructive task point to a deeper issue of contrasting cultural assumptions and grounding principles, allowing a better understanding of what lies at the heart of the philosophical divide between ''East'' and ''West.'' Each embraces a strategy of fruitful opposition: gadfly Nietzsche approaches his predecessors with wariness and righteous wrath; butterfly Zhuang Zi co-opts Kong Zi, and confounds Hui Zi. The distinction between opponent and competitor parallels that between wu-wei effortlessness and wei aggression. Despite an intuitive grasp of the child's 'yes' to life, wu-wei, Nietzsche remains mired in a defective wei strategy, while Zhuang Zi's Daoist deconstruction takes the form of wu-wei philosophical play.