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.
While in Israel, the narrator seeks out an impersonator who has appropriated his identity—sharing the same facial features and name as Philip Roth—and used this celebrity to spread "Diasporism," a counter-Zionist ideology advocating the return of Israeli Jews to their European nations of exile. 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.
A major concern of Roth's fiction since the 1970s has been the relationship between a novelist's life and work. 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.
Despite this effort, separating the real from the fictional in Operation Shylock is not wholly impossible. For example, several minor characters from the novel are actual people including John Demjanjuk, Claire Bloom, and Israeli writer and Roth friend Aharon Appelfeld. The post-operative nervous breakdown mentioned in the prologue and in other books by or about Roth was drawn from Roth's real-life experience of the temporary side-effects of a post-operative sedative (triazolam) which was later banned in several countries after discovery that the manufacturer had not published studies showing a high risk of short term psychiatric disturbance.
 Roth's "Confession"
In March 1993, he maintained the veracity of his novel to The New York Times' Esther B. Fein: "'Operation Shylock,' Roth insists with a post-modern straight face, is a 'confession,' not a novel, and he means for us to take this every bit as seriously as the contents labels demanded by the strictures of the Food and Drug Administration. 'The book is true,' Roth said the other day. 'As you know, at the end of the book a Mossad operative made me realize it was in my interest to say this book was fiction. And I became quite convinced that it was in my interest to do that. So I added the note to the reader as I was asked to do. I'm just a good Mossadnik.'"
Roth's long-time professional acquaintance John Updike gave the novel a famously caustic review in The New Yorker. 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." Updike closed with the admonition, "It should be read by anyone who cares about (1) Israel and its repercussions, (2) the development of the postmodern, deconstruction-mInded novel, (3) Philip Roth." In The New York Times Book Review, novelist and poet D.M. Thomas called the novel "an impassioned quarrel...Despite the seriousness of its theme, the book carries the feeling of creative joy. One feels that Roth feels that he's let rip."
The novel appears to have grown in stature since publication. In 2006, when New York Times Book Review editor Sam Tanenhaus mailed a short letter to "a couple of hundred prominent writers, critics, editors," asking that they identify the best work of American fiction published in the preceding quarter-century, several respondents named Operation Shylock. (The eventual winner was Toni Morrison's 1987 Beloved.) Reporting upon Roth's reception of the 2011 Man Booker International Prize, critic Jonathan Derbyshire of the New Statesman wrote, "The judging panel make the inevitable reference in their summing-up to Roth's extraordinary fecundity over the past 15 years or so, at a stage in his life when 'most novelists are in decline'. The most notable fruits of Roth's Indian summer, 1995's 'Sabbath's Theater' and 'American Pastoral', published two years later, are certainly among his most luminous achievements. 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.'"
Operation Shylock received the 1993 PEN/Faulkner Award for best novel. Roth would eventually become the first three-time winner of the award: for Shylock, 2001's The Human Stain, and 2007's Everyman.
- p5, Philip Roth, The Facts: A Novelist's Autobiography, Random House, 2011: "I'm talking about a breakdown. Although there's no need to delve into particulars... what was to have been minor surgery... led to an extreme depression that carried me right to the edge of emotional and mental dissolution. It was in the period of post-crack-up medication, with the clarity attending the remission of an illness..."
- p79, Timothy Parrish (ed.), The Cambridge Companion to Philip Roth, Cambridge University Press, 2007: "In point of fact, Roth's surgeries (one the knee surgery, which is followed by a nervous breakdown, the other heart surgery) span the period..."
- pp108-9, Harold Bloom, Philip Roth, Infobase Publishing, 2003
- Adam K, Oswald I (May 1993). "Triazolam. Unpublished manufacturers research unfavourable". BMJ 306 (6890): 1475–6. doi:10.1136/bmj.306.6890.1475-b. PMC 1677863. PMID 8292128.
- Bramness JG, Olsen H (May 1998). "[Adverse effects of zopiclone]". Tidsskr. Nor. Laegeforen. (in Norwegian) 118 (13): 2029–32. PMID 9656789.
- Kales A (September 1990). "Benzodiazepine hypnotics and insomnia". Hosp. Pract. (Off. Ed.). 25 Suppl 3: 7–21; discussion 22–3. PMID 1976124.
- Manfredi RL, Kales A (September 1987). "Clinical neuropharmacology of sleep disorders". Semin Neurol 7 (3): 286–95. doi:10.1055/s-2008-1041429. PMID 3332464.
- Esther B. Fein, "Philip Roth Sees Double. And Maybe Triple, Too," The New York Times, March 9, 1993.
- D.T. Max, "Twilight of the Old Goats," Salon, May 16, 1997. ("According to [Claire] Bloom's memoir, Roth blamed Updike's harsh New Yorker review of 'Operation Shylock' for his decision to check into a psychiatric hospital.")
- John Updike, "Recruiting Raw Nerves," The New Yorker, March 15, 1993. In the essay, Updike gets down into the structural weeds: "Relentlessly honest, Roth recruits raw nerves, perhaps, because they make the fiercest soldiers in the battle of truth...Never impressionistic in his style, Roth began [in Goodbye, Columbus] with sensory facts, arranged and presented in a prose not quite colloquial, but simple and clear. Under the stress of the intricate questions his later fiction poses, his sentences stretch, and turn a bit stentorian. A diagrammatic grayness creeps in as the complications thicken."
- D.M. Thomas, "Face to Face with his Double," The New York Times Book Review, March 7, 1993.
- The New York Times, "What Is the Best Work of American Fiction of the Last 25 Years?", May 21, 2006.
- Jonathan Derbyshire, "Philip Roth wins the Man Booker International Prize," New Statesman, May 18, 2011.
- The Associated Press, "Philip Roth Wins Literary Award," February 26, 2007. (For his novel Everyman. "Roth is the first three-time winner of the PEN/Faulkner, having received it in 1994 for 'Operation Shylock' and in 2001 for 'The Human Stain.'")
- Roth on Operation Shylock in The New York Times
- D.M. Thomas on Operation Shylock in The New York Times Book Review