This thesis explores the mysterious Pollard affair, a tense episode of espionage and diplomatic crisis that transpired during the mid-1980s, toward the tail end of the Cold War. The spying and subsequent capture of Jonathan Pollard, an American Jew, to benefit Israel led to a reckoning in the relationship between the American and Israeli governments, between the American Jewish community and Israel, and between the American Jewish community and the U.S. government. Although Israel and the United States had a close and enduring working relationship at the time, Pollard received a life sentence. He was released on parole in 2015, and his parole restrictions were lifted in 2020, after which he immigrated to Israel. This paper will argue that the greatest damage caused by the lengthy Pollard affair was that which was inflicted upon the American Jewish community’s relationship with Israel. The effects of the scandal on the government-to-government relationship, on the other hand, were not as profound. The espionage episode exacerbated a slowly growing willingness among American Jewry to openly criticize Israeli policies, something that the community had previously been quite reluctant to do. Understanding the ripple effects of the Pollard affair — both within the two governments, as well as among American Jews and Israelis — can shed light on the nature of the long-standing, close, and multi-faceted relationship between the two countries.