The novel follows narrator "Philip Roth" on a journey to Israel, where he attends the trial of accused war criminal John Demjanjuk and becomes involved in an intelligence mission—the "Operation Shylock" of the title.

The ensuing struggle between this doppelgänger-like stranger and "Roth", played against the backdrop of the Demjanjuk trial and the First Intifada, constitutes the book's primary storyline.

Though this topic is thoroughly explored in Roth's series of Zuckerman novels, Operation Shylock even more radically attacks the distinction between art and life by making a fairly mimetic version of the author the protagonist of an obviously invented (though plausible) story.

For example, several minor characters from the novel are actual people including John Demjanjuk, Claire Bloom, and Israeli writer and Roth friend Aharon Appelfeld.

[10] Updike found the book "an orgy of argumentation...this hard-pressed reviewer was reminded not only of Shaw but of Hamlet, which also has too many characters, numerous long speeches, and a vacillating, maddening hero who in the end shows the right stuff."

But two slightly earlier novels stand out for me, both of them hectically metafictional works partly set in Israel: The Counterlife (1986) and Operation Shylock."

Daniel Mendelsohn cast his vote for Operation Shylock, writing: "Here, the coruscating linguistic brilliance, the profanity and playfulness (and the deep, often irritated engagement with Jewishness) that characterizes his earlier novels rise to new — and, I would say, philosophical — heights.

For the two Roths finally meet in a Jerusalem that is anxiously hosting the trial of John Demjanjuk, the Ukrainian-born Ohio autoworker who was revealed to have been a sadistic guard at a Nazi death camp: a setting that amplifies the significance of Roth's favorite themes of identity and imposture, truth and fictionality, and gives the ostensibly zany, Quixote-esque plot an ultimately tragic historical resonance.