This chapter describes the enthusiastic involvement of young Highland Scots, after 1796, in the slave plantations of modern Guyana (the former colonies of Demerara, Essequibo and Berbice). This was despite the high risk of death from disease and the relatively small chances of success. The central argument of the chapter is that historians need the insights of the new discipline of behavioural economics to provide adequate explanations of why, as in this case, so many individuals acted against their best interests in making these choices. The behaviour of these migrants is examined in detail using key concepts from the work of Daniel Kahneman, Amos Tversky, Cass Sunstein and Richard Thaler, namely the availability heuristic, stereotypes and the representative heuristic, anchoring effects, loss aversion and framing effects. These concepts allow us to better understand both how the prospects facing those who chose to migrate appeared to the individuals making the decisions, and why they systematically misjudged the likely outcomes. Finally, it is suggested that this approach may have wider application to the ‘paradox of Scottish emigration’ －the historical puzzle of why so many Scots emigrated at a time when prospects at home were improving.