On 9 July 1967, Leonard Bernstein led the Israel Philharmonic Orchestra (IPO) in a concert atop Mount Scopus, celebrating in the aftermath of the Jewish State’s geopolitical victory in the Six-Day War. Even as explosions thundered on in the distance, Bernstein publicly championed Jerusalem’s destiny to be a peaceful, unified city in which all could flourish through increased cultural tolerance. This event is perhaps more indicative than any other of the contradictions between Bernstein’s personal and political beliefs as a progressive, first-generation Jewish American and his deeply ingrained, lifelong loyalty to Zionism and Israeli nationalist sensibilities. This chapter briefly explores how these oft-conflicting belief systems and historical events shaped Bernstein’s lifelong struggle to negotiate his identity as an American New Jew.