Fair trade commonly focuses on the figure of the smallholding peasant producer. The effectiveness of this as a strategy lies in the widespread appeal of an economy based upon independent family producers trying to secure livelihoods in impersonal and exploitative global commodity markets. But the attempt by fair trade to personalise economic relationships between coffee producers and consumers diverts attention away from aspects of the political economy of production for the market. This chapter examines a rural Costa Rican coffee economy that has supplied fair trade markets since the 1980s. Documenting differences in landholdings, the range of activities farmers engage in, and the relationship between landowners and landless labourers, women, and migrant harvesters from Nicaragua reveals differentiation and tensions that are obscured in the “smallholder” model invoked by fair trade.