This research is an initial exploration of how members of one Hispanic subculture (Cuban Americans) were socialized into sport participation and spectating across multiple generations. Through 16 in-depth interviews with Cuban Americans across three generations, the researchers explored Cuban Americans’ values relative to sport and identified socialization agents that were the primary contributors to their socialization into sport. It was confirmed that family plays a primary role in sport socialization for this subculture. We also found the presence of retroactive socialization—a child socializing the parent/grandparent into sport—and suggest that neither school nor sport coaches are key socializing agents for this particular subculture. We also determined there were differences in sport socialization across generations.