This essay begins with an introduction to the essence of transformational diplomacy, as well as its relationship with the U.S. national security strategy. In addition, this essay examines how mainland China views transformational diplomacy. It also presents three potentially controversial inferences on transformational diplomacy's influence on Taipei, Beijing, and Washington. Three important conclusions of this essay are: (1) because of the ”peaceful evolution” nature, transformational diplomacy can be one of the key variables influencing foreign relations between the PRC and the U.S., but not now; (2) political and military arguments between the PRC and the U.S. will loom large as transformational diplomacy is being carried out, but triangular Washington-Beijing-Taipei relations might change dramatically not due to transformational diplomacy but three sets of sensitive bilateral relations among them; (3) without engaging mainland China in a proactive way, Taiwan's role in U.S.'s peaceful evolution strategy toward China will be less significant.