A large amount of Latin American popular, folk, and art music circulated in the United States during the twentieth century. It was not just popular music composers that had dialogue with it; classically trained composers such as Leonard Bernstein also did. However, more than the music tradition that Bernstein absorbed into his compositional language in works such as On the Town (1944) and West Side Story (1957), this chapter argues that Latin American music also served as a medium to express Bernstein’s ideas and feelings about the US socio-political and cultural landscape. Furthermore, the chapter shows that Bernstein’s dialogue and collaboration with Latin American composers at the Tanglewood Music Festival, conducting the New York Philharmonic during the Latin American tour (1958), and performing Latin American music works at the Young People’s Concerts (1958−72), all contributed to and enhanced his vision as a cultural broker.