In 2014, mainland Chinese collector Liu Yiqian bought a Ming dynasty Chenghua-period chicken cup from the European-based Meiyintang collection, at a Sotheby’s auction for US$36 million. The record-breaking price brought public interest to the chicken cup which was well-known in antique collecting circles. The sale focussed attention on the topics of the Chenghua era, Western collectors, and the contemporary mainland Chinese buyers. This thesis examines these three areas to discover the rich and complex representation of the chicken cup over its lifespan of more than 500 years. The study analyses the chicken cup’s transformation from a wine vessel to a collectable antique, and from a work of art to the ‘Holy Grail’ among today’s collectors. Art historical methodologies are employed to assist the discussion in this thesis, including theories of iconography, material culture, biography and social history, connoisseurship and philosophy of aesthetics. The study reveals that the chicken cup often speaks on behalf of extant chicken cups and other antique treasures. Importantly, it epitomises a complicated imperial narrative, provides evidence of the development of Western taste in Chinese aesthetics and exemplifies the ardent pursuits of contemporary mainland buyers. The multifaceted significance demonstrated in this research attempts to fill the academic gap for this eminent piece of historical porcelain, acknowledging the necessity of using multiple viewpoints to adequately evaluate its place in history. This offers a model for application to investigate other forms of Chinese art.