This chapter examines the rise and fall of Chinese indentured labor in Cuba during the mid-nineteenth century. Between 1847 and 1874, nearly 125,000 Chinese workers (often referred to as coolies) arrived in Cuba to supplement the African and African-descendant slave labor force. While these workers legally were not enslaved, their daily experience closely resembled slavery. By 1874, international pressure helped shut down the “coolie trade” to Cuba. However, as this chapter argues, Chinese workers themselves played a crucial role in undermining the indentured labor system on the island. They regularly resisted their exploitation. Individual acts of resistance could ameliorate daily hardship or help an individual obtain freedom even if they could not overthrow the system. Nevertheless, resistance had cumulative power. As these workers pursued everyday and radical forms of resistance, they engaged and exposed the contradictions and hypocrisy of the coolie labor system. In the process, they drew increasing domestic and international attention to their plight. Chinese resistance became a constant reminder that supposedly legally free men were being treated as if they were slaves and that this mockery of free labor ideals needed to end. Thus, the Chinese helped create the pressure to end the coolie labor system in Cuba.