High-value export-oriented agriculture is today considered as a means of integrating smallholders into the world economy. This paper examines the geographic and organisational changes that have taken place in the fresh pineapple sector over the past 50 years. We begin with a historical analysis of the changes in leadership among producer countries, namely the dethroning of Côte d’Ivoire by Costa Rica. We show that this geographical shift has been accompanied by massive organisational changes: the pineapple sector is increasingly driven by large downstream actors who derive their power from the ability to impose their definition of quality to the whole chain, and from economies of scale and scope. Although varietal innovation plays a key role throughout the period, commercial and logistical innovation are of increasing strategic importance. However, because of the constraints imposed by the concerned supply chains, small farmers risk being excluded or marginalized.