Chance-based gambling has been a recurrent cultural activity throughout history and across many diverse human societies. In this paper, I combine quantitative and qualitative data and present a cultural evolutionary framework to explain why the odds in games of chance in premodern China appeared “designed” to ensure a moderate yet favorable house advantage. This is especially intriguing since extensive research in the history of probability has shown that, prior to the development of probability theory, people had very limited understanding of the nature of random events and were generally disinclined to think mathematically about the frequency of their occurrence. I argue that games of chance in the context of gambling may have culturally evolved into their documented forms via a process of selective imitation and retention, and neither the customers nor the gambling houses understood the probability calculus involved in these games.