The purpose of this study is to explore the principles of school leadership by comparing the characteristics of Xiang Yu (項羽) and Liu Bang (劉邦) as described in Sima Qian's "Records of the Grand Historian" (史記). To achieve this goal, the study examines the leadership types observable in "Records of the Grand Historian" and compares the contrasting leadership styles of Xiang Yu and Liu Bang, ultimately seeking to uncover the leadership qualities required by school principals in today's context. The results are as follows: "Records of the Grand Historian" (史記) depict into the inquiry of attributes of an ideal leader through the descriptions and assessments of historical figures. Consequently, an examination of "Records of the Grand Historian" enables us to explore the value factors that school principals should embody in their leadership. The depiction of a successful leader in "Records of the Grand Historian" (史記) is one who is grounded in humanistic values, has a grand vision, strives to realize the common good of the community, and possesses qualities of active listening and inclusivity. By comparing the contrasting leadership styles of Xiang Yu and Liu Bang, two historical figures featured in "Records of the Grand Historian" (史記) whose leadership stands out most distinctly, and applying these insights to school leadership, the study suggests that school principals should present a vision that aligns with the current situation, listen to and embrace the opinions of the members, and be aware of their own shortcomings while appropriately delegating authority to the teachers.