Tongxuan's 100 Chan Questions is a significant Zen Buddhist koan collection. It includes dialogues about philosophy and religious practice expressed through paradoxical sayings and puzzling poems. This thirteenth-century text, included in the supplementary Buddhist canon, was composed by several leading figures of the Caodong Chan Buddhist school in China, who were part of an important sublineage located in Beijing and supported by the emerging Mongol rulers. The collection thus represents the literary production of a crucial, though lesser-known, phase of Caodong Chan history based in a branch situated in the northern territories that thrived at the dawn of the Yuan dynasty. The text of Tongxuan's 100 Chan Questions demonstrates key aspects of Caodong discursive practice, reflecting the school's philosophy that Chan transmission should be based on a rhetoric of minimalism, or an exceptionally concise and cryptic writing style that conjures how “to speak without speaking.” This technique is particularly suited to cultivating a manner of contemplative training based on the notion of pragmatism, or the application of a nondual standpoint to examples of everyday moral decision-making. This elegant translation of Tongxuan's 100 Chan Questions with insightful commentary on the meaning and symbolism of the cases provided by the author shows how and why the collection was compiled by several generations of Chan monks who gained the support of the Mongol government. Steven Heine examines the diverse ways in which the text's Zen sayings and poems were influenced by a wide variety of sources encompassing Buddhist sutras, Daoist parables, Confucian dictums, Chinese literary compositions, and traditional East Asian folklore and mythology.