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This chapter examines the similarities and differences between the concepts of transformational leadership as developed within North America and the Confucian idea of transformation. It argues that Confucian tradition encompasses the essential elements embedded in the concept of transformational leadership. The former differentiates from the latter in its deeper degree of transformation, emphasis on morality and culture, and its focus on transformation from the inside outwards. The two greatest educators in Chinese history, Confucius and Cai Yuanpei, are evaluated in terms of their transformational leadership qualities in the Western sense. By looking at Confucius and Cai Yuanpei as successful transformational leaders, the chapter identifies four important factors from Chinese cases that may contribute to the success of this type of leadership. Implications of this comparison are discussed as they may inform the knowledge, research and practices of transformational leadership.