The Chinese criminal underworld is evolving along two paths: structural and territorial-based triads and criminal groups formed by entrepreneurs. The present study used triad involvement in casino VIP rooms to examine how these two paths cross after China resumed sovereignty of Macau in 1999. It was found that although the current operations of the junket business is determined by the external business environment in mainland China, triads continue to treat the VIP rooms as economic territories. New forms of betting and crime have emerged to meet the needs of high-end gamblers, thus resulting in the formation of a triad-enterprise hybrid that comprises territoriality and reputation of violence commonly found in extra-legal governance and the dynamic entrepreneurship of small firms.