As a synthesizer of the Māhayānic Prajñāpāramitā tradition in the early development of Chinese Buddhism, Jizang (549–623 CE) was one of the most important representatives of the Sunlun School (aka. The Three-Treatises School), whose doctrine centers on emptiness. This paper concerns the unfolding of the deconstructive strategies in Jizang’s rendering of the four levels of twofold truth, demonstrating how Jizang’s method of negation as a form of “critical philosophy” is utilized to correspond to the Sanlun appropriation of the Madhyāmikan understanding of emptiness. According to Jizang, the doctrine of the twofold truth functions as a pedagogical means, aiming to achieve two major purposes: (1) to put forth a critique of both nihilist and absolutist interpretations of emptiness; and (2) to resolve certain obscurities and inconsistencies in the teachings within the Buddhist tradition. The author submits the idea that the Sanlun philosophy exhibits a more positive attitude toward the conventional through Sinicized conceptualization of the Middle-Way-as-Buddha-Nature, and that the Sanlun thought is more dependence upon affirmative expressions (i.e. kataphasis) than negative ones (i.e. apophasis) to promulgate its thesis. The paper concludes by pointing out that the Jizang’s method of negation has a significant impact on the later development of Chinese Buddhism, such as the Tiantai school’s doctrine of Emptiness-Provision-Middle and the Chan Buddhist teaching of non-abiding.