Merchants were an important feature of the ancient commercial landscape. This chapter examines the merchant’s dilemma, the conditions that gave rise to their appearance, and the way that merchants operated in the ancient world. Structures of operation discussed include commenda partnerships, diaspora communities, and the role merchants played in the development of the putting-out system of managed production. Examples discussed include tribal merchants in New Guinea and South India as well as merchants in the state-level societies of Bronze Age Assur and Aztec Mexico.