This chapter examines Bernstein’s complicated relationship with the Soviet Union. Born four years before the creation of the Soviet Union and dying eleven months after the fall of the Berlin Wall, his life story, including his rise to global prominence, paralleled the history of the Soviet republics. As an American of Ukrainian heritage, the composer had personal ties to the region. I examine these family connections and their complexities; his lifelong interest in Russian classical music; his period of attraction to Communism as an ideology, its consequences, and his statements in support of US–Soviet peace; and his 1960 cultural-diplomacy-related tour of the USSR with the New York Philharmonic. Ultimately, I argue that the United States’ relationship with the USSR had a profound impact not only on his family life and conducting career, but also on his attitudes to music-stylistic choices.