At the heart of urban tourism promotion lies a triad of powerful players—the city, the hotels, and the destination marketing/management organization (DMO). This article explores the relationships between the DMO, charged with crafting and executing destination promotion, and its two most powerful stakeholders—the city (or urban government) and hotels (or accommodation sector). Empirical insights are derived from an examination of three major North American city destinations. In each setting, in-depth key informant interviews were conducted with leaders of each member of the triad (the city, the hotels, and the DMO). The triad is found to be asymmetrical with each member bringing a unique and complementary resource. The extent to which members of the triad can effectively relate to one another and combine their complementary resources is posited to be an important determinant of success in destination promotion.