This article foregrounds the returns of migration by following young migrant workers to Lebanon and back to subsistence farming communities in western Sudan during a time of revolution and economic crisis in both countries. Their labor and the returns of it connect these two seemingly distinct zones of labor and production in a transregional economy, linking East Africa to the Middle East. In this cross-border economy, the search for work through mobility has become a point of value extraction by brokers and border guards, and at the same time a practice of gendered self-validation for male migrants. In Sudan, migrants and brokers both refer to this practice as a gamble, mughamara. Proposing mughamara as an ethnographic concept of mobility, I show how young migrants use this term to validate themselves through migration. Comparing their experiences to Sudanese migrants who worked in Lebanon decades before them, I show how the youth’s presentation of mobility as a necessary gamble with life reveals an underlying generational experience of crisis and the foreclosure of class mobility. In a political and socioeconomic context where migrant workers often feel devalued in and by labor, mobility is presented as their only way forward—as well as their ticket home.