The Wenzi (Master Wen or The Cultured Master) is traditionally attributed to its eponymous thinker, yet little is known about him. The absence of biographical information has led scholars to investigate his historical identity, but with no definitive results. This chapter takes a different approach by shifting the focus from Wenzi as a historical figure to the origins of the legend of his discipleship under Laozi (Master Lao or The Old Master). When and where did the idea of Wenzi as Laozi’s disciple emerge? The analysis unfolds in three main sections. The first surveys early Chinese texts for references to Wenzi as Laozi’s disciple. The second explores textual links between the Wenzi and the Laozi. The third examines the two central figures in the Wenzi to determine what they reveal about the master-disciple relationship. The conclusion reflects on the broader implications of these findings and proposes a hypothetical scenario for the legend’s emergence. Ultimately, this chapter seeks to illuminate how the legend of Wenzi’s discipleship relates to the origins of the Wenzi itself—its connections to the Laozi and its philosophical underpinnings. Positioned at the intersection of early Daoist history, mythology, intertextuality, and philosophy, this study clarifies what current evidence allows us to conclude while acknowledging the uncertainties that remain.