Men are seldom a topic of concern in migration research as gendered subjects who experience the implications of social justice, for instance in aspects relating to lives in their families such as fairness of representation, consequences of material redistribution, and management of emotions. Economic migrants in particular, who are seen as matching the role of breadwinners and confirming the status of dominant patriarchal men, are a particularly underrated case. Using the experiences of Wolof men who emigrate from Senegal to become the main providers for their families, this chapter questions this assumption by drawing insights from a theorization on ‘transnational families’, ‘intersectionality’ and ‘masculinity’ as developed within migration and gender studies. The chapter discusses how male gender roles become interlocked with other categories, as asymmetries (be they real or perceived) intervene between the migrant and the left-behind, and as geographic distance forces them to revisit the propriety of arrangements that enable them to enact their gendered responsibility within families. Caught between pressures deriving from their economic and moral obligations towards family and kin on the one hand, and personal aspirations of fitting the part of successful men on the other, the ethnographic research presented in this chapter shows that migrants engage in an emotional journey that may challenge, rather than confirm, their expectations of ‘hegemonic’ masculinity