Abstract This paper focuses on the subject of the cocoa transfer agreements and the transformation of rural agrarian livelihoods in the cocoa belt of South West Nigeria under the Structural Adjustment Programme (SAP). The paper maps the trajectory and career of three dominant agricultural entrepreneurs in the cocoa produce trade in South West Nigeria during the 20th century. The paper demonstrates that while the cocoa business in Nigeria has received considerable scholarly attention, the impact of moneylenders, public letter writers (PLWs) and cocoa transfer agreements on cocoa business, rural livelihoods and entrepreneurship in the aftermath of SAP is yet to be fully investigated. Analysing the accumulative strategies and contributions of Emmanuel Akintan, Isaac Adegbuyi Akingboye and Rufus Orosundafosi to rural capital formation, the paper highlights the impacts of liberalisation policies on African rural businesses in the aftermath of SAP. The paper combines primary sources, such as oral interviews, personal observation and ethnography, with information collected from the archives, newspapers, diaries, and extant literature to analyse the dynamics of rural accumulation in the cocoa producing South West Nigeria during the 20th century. The paper argues that the acquisition of wealth and the thin line between standard procedures and clandestine deals stimulated accusations of dispossession of peasant farmers by the capitalist moneylenders and merchants in the post-SAP era.