Gambling has long been comprehended as activities involving money wagering or other belongings for random or uncertain outcomes and causes the risk to chains of problems to the individuals, ranged from financial problems, psychological problems, and interpersonal problems. Maladaptive gambling behavior has also been classified in DSM-IV, named as pathological gambling (312.31), and is considered as illegal practice in many countries, including Indonesia. Gambling activities as a tradition also exist in various cultures, such as ‘tajen’ in Bali, Indonesia. ‘Tajen’ is a cockfighting tradition and a part of religious rituals in Bali. This has resulted in a unique problem regarding to its cultural and legal context, while the risk to psychological problems (such as pathological gambling) cannot be disregarded. Using the case of Tajen in Bali, this paper also discusses the influences of culture to gambling behavior and its legal complexity.