In this article, we investigate the individual and contextual factors that explain trust in Latin American labor unions. Utilizing data from Latinobarómetro (2018–2020), we show that trust in unions is higher among working-class and salaried middle-class individuals, and among those who identify with the left and exhibit greater confidence in political institutions. On a contextual level, trust in unions is higher in neo-developmentalist countries (e.g., Brazil, Uruguay) and lower in outsourced capitalist nations (e.g., Mexico, Central American countries). Contrary to our initial hypothesis, we also find that trust in unions is high in Chile—a liberal-rentier country with weak unions—and low in some redistributive-rentier (e.g., Venezuela) and neo-developmentalist countries (e.g., Argentina). To explain these findings, we examine how trust in unions is influenced by contextual factors such as labor informality, unemployment, inflation, the strength of left-wing parties, and the country’s level of social mobilization.