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The Seasonal Agricultural Worker Program (SAWP) is a transnational labour agreement between Canada, Mexico, and various Caribbean countries that brings thousands of Jamaican migrant workers to Canada each year to work on farms. This thesis explores Jamaican SAWP workers’ experiences of stress in Ontario, and situates these experiences within a system of power and international inequality. When describing their experiences of stress and suffering in Ontario, many Jamaican workers drew analogies between historic and modern slavery under the SAWP. However, stress discourses also inspired workers to emphasise their resilience, and many workers gave equal attention to explaining their inherent strength as “Jamaicans”, which they associate with national independence and the history of slavery. In this way, I suggest stress discourses are sites of flexibility and resilience for Jamaican workers, and this thesis presents the foremost cultural, political, and historical factors that support Jamaican workers’ resilience in Ontario. Moreover, the predominant coping strategies workers employ in Ontario will be explored within the context of their restricted agency under the SAWP. This thesis concludes with a discussion of stress as an expression of subjectivity that is characterised by strength, faith, and the history of slavery.