The desire to forge personal and collective destiny is nowhere more acute than in Havana’s Chinatown (Barrio Chino). As a historical bridge between Cuba and China and a profitable tourist attraction, but also a hub of unregistered trade, the district concentrates nationally pertinent opportunities and threats into twenty-three city blocks. Commercial networking underpinned the economic and social security of indentured Chinese workers and other migrants in the nineteenth and twentieth centuries. Today their descendants are pioneering the expansion of social networks to mainland China and breathing new life into Barrio Chino’s profitable restaurants. As transpacific relationships thicken, the trust underpinning them is creating unprecedented dilemmas for the Cuban state. Unable to contain the inflow of kitchen equipment, medicines, and money, administrators are becoming more responsive to local demands for infrastructure improvements and commercial leeway. The case of Barrio Chino demonstrates how trust on the ground is shaping the trajectory of Cuba’s national and international evolution.