In the beginning of the seventeenth century, Geng Ju, the magistrate of Changshu county, restored Yushan Academy. Scholars gathered from every quarter to discuss Neo-Confucian philosophy at the academy, which swiftly became an important intellectual hub in the Jiangnan region. The Wanli edition of Yushan Academy Gazetteer, compiled under the leadership of Geng's colleague, Zhang Nai, recorded many scholarly debates between Geng and other contemporary scholars associated with the Academy. Hence, this gazetteer remains an important resource for our understanding of late Ming intellectual history. Chapter 14 of the gazetteer includes an anthology of philosophical debates about life, death and samsara between 20 scholars at the academy, led by Geng and Zhang. They also creatively reinterpreted concepts from the Analects, including the passages, "One who hears the Dao in the morning may gladly die in the evening," and "How can one know death when life is not yet known?" The scholars took varying stances on life, death and samsara from different types of backgrounds and intellectual lineages, with positions ranging from the orthodoxies of the Cheng brothers and Zhu Xi, to Confucian ideas tinged with Zen Buddhism, to a syncretic blending of the Three Teachings. Comprehensively preserved in the gazetteer, these debates certainly provide a major contribution to our understanding of late Ming Confucianism. Previous scholarship on Yushan Academy is very limited, with Geng Ju, Zhang Nai, and their peers barely making an appearance. The analysis in this essay focuses on the background and concerns of this debate and how it proceeded, defining and positioning the philosophical standpoints of Geng and Zhang, as well as the general intellectual atmosphere at Yushan Academy, locating it within the wider context of Ming intellectual history, in hope of sparking attention and discussion on the subject.