Operation Shylock tells the story of an American Jew author, Philip Roth, who hears that someone has been using his name in Israel to promote the ideology of Diasporism, that the European Jews of Israel should return to their homelands in Europe. The protagonist narrator, the author Philip Roth, seems to be based on the author of the book itself. If the story told were not so absurdóPhilip Roth eventually becomes a spy for the Mossadówe might believe that the story is in fact what its subtitle suggests, a confession. The rogue Philip Roth is never given a true identity, but instead exists to the protagonist as Moishe Pipik, Yiddish for Moses Bellybutton.
After recovering from a debilitating experience from a prescription medication, Halcion, Philip learns of his impostor. He initially wonders if it could just be another drug-induced hallucination. Yet he soon determines that it is all too real. As scheduled, he travels to Israel to interview the Israeli author Aharon Appelfield. However, most of his time is spent in conversation with Pipik, at the trial of John Demjanjuk , or with college friend and now-ardent-Arab George Ziad, whom Philip initially leads to believe that he and Pipik are one and the same.
Philip alternates between imitating Pipik (who is imitating him) and attempting to discover Pipik's real motivation behind his Diaspora initiative. Philip discovers Pipik's girlfriend, Jinx, and has an irresistible attraction to her. From her, Philip learns about Anti-Semites Anonymous, a support group designed by Pipik to correct Gentiles of anti-Semitism just like Alcoholics Anonymous corrects alcoholism. Over the course of the narrative, he picks up other bits and pieces of information about his impostor. He discovers that Pipik, a former private investigator, has cancer as well as a penile implant to please Jinx.
This report prepared by Whitney