The present chapter discusses the cultural implications of AI and its regulation by taking the example of Macao, a Special Administrative Region of the People’s Republic of China. Macao features many unique characteristics, such as being a free port and self-standing WTO member, or a multicultural place where “East meets West”. Overall, Macao’s economy, its hybrid legal system and wider political and cultural identity provides an interesting framework for a brief evaluation of its strategy for digital transformation and related AI policies. More concretely, the chapter argues that, as a consequence of Macao’s unique history having shaped its political, economic and cultural characteristics, the regulatory toolkit that it will develop in the near future will necessarily need to reflect the multicultural, multi-ethnic and multilingual identity of this complex city. In particular, there are three elements that seem to emerge as key to the development of culturally-sound framework: the public/private divide, China’s role under the multi-level governance principle of “One country, two systems”, and Macao’s role as a bridge connecting the East with the West. In summary, the chapter puts forward the idea that Macao legal reality as a “glocal” actor can contribute to the much-needed global debate on AI and data governance by serving as a regulatory laboratory for the experimentation with regulatory instruments created to address the many problems and challenges framed as oxymora and paradoxes that arise in this field.