In the early days of the pandemic, when much of the world had shifted to Zoom and other online video platforms, the New York Times ran an article about what has become known as “Bookcase Credibility.” The article explained that “as the broadcast industry shelters in place, the bookcase has become the background of choice for television hosts, executives, politicians, and anyone else keen on applying a patina of authority to their amateurish video feeds.” The placement of books in a library or bookcase sends a certain message, and people have intentionally rearranged their bookcases and libraries as more of the outside world gains access to it.
Even before Zoom, people have, of course, been intentional regarding their book placement. Not bound by the organizational needs and constraints of a lending or research library, private citizens can arrange their bookshelves according to whatever convenient, haphazard, or, in many cases, amusing system they see fit. I know people, for example, who like to show off their bookshelves where they have arranged unlikely pairs near each other. Books authored by halakhic or philosophical rivals, or by people with strongly opposing religious views, can be put next to each other for comedic effect.
On my own bookshelf, I have three books near each other, almost identically titled but with very different contents. These are: What Ifs of Jewish History: From Abraham to Zionism, edited by Gavriel D. Rosenfeld; What If? Serious Scientific Answers to Absurd Hypothetical Questions by Randall Munroe (currently in one volume, with a second one coming out later this year); and What If? Fascinating Halachic Discussions for the Shabbos Table, Arranged According to the Weekly Torah Reading by Rabbi Yitzchok Zilberstein and Rabbi Moshe Sherrow (currently in seven volumes, five on the Torah and two on the holidays).
Although representing very diverse subjects, these books’ common use of the title “What If” implies a related purpose, namely the use of hypothetical situations as the basis for exploration of larger questions. These hypothetical discussions differ greatly depending on the genre. While hypotheticals in history and science generally remain on a speculative plane, hypotheticals in Halakhah (or Jewish law) can have serious real-world implications where logic and reasoning can serve as the basis for a ruling in an actual situation.
In the world of academic history, “What Ifs” represent a genre known as counterfactual or virtual history and is the subject of our first book. Gavriel D. Rosenfeld’s What Ifs of Jewish History contains a collection of essays by leading historians based on counterfactual Jewish history, analyzing the effects and impact of historical occurrences and how things would have looked had events transpired differently. Topics discussed include: what if the Exodus never happened, and what if the Temple in Jerusalem had not been destroyed by the Romans? In recent years, this type of history has become a respectable academic pursuit with more historians writing “What If”-style articles and books. In a masterful essay that both charts the history of counterfactual history and succinctly describes the value of its study, historian Niall Ferguson writes, “To understand how it [history] actually was, we need to understand how it actually wasn’t―but how, to contemporaries, it might have been… Virtual history is a necessary antidote to determinism.”
A drawback of this kind of history, however, is that it can easily devolve into fantasy, where the counter history is no more than a plot device and does not necessarily further the understanding of the true history. Interspersed with the counterfactual historical essays in Rosenfeld’s work (the book is arranged chronologically) are several chapters that are works of fiction, also written by leading historians. These essays are indicated as fiction with a note at the start of the respective chapter (although regrettably not in the table of contents), and they lack proper footnotes or any other scholarly apparatus. There is also no real historical analysis that would explain why the presentation is anything more than pure fiction and, by extension, no argument why they belong alongside the nonfiction essays in the work. To be clear, I am not critiquing this particular genre; rather, I am noting the difference between a “What If” that is primarily for the purpose of entertainment and one which is designed for historical analysis and showing how easily the two are blurred.
Our second “What If” book is by Randall Munroe, an American cartoonist best known for his comic xkcd (“a webcomic of romance, sarcasm, math, and language”). He has also written several bestselling books on science, including the aforementioned What If: Serious Scientific Answers to Absurd Hypothetical Questions. Based on his blog by the same name, Munroe answers unusual questions sent in by readers on topics as diverse as “What would happen if you tried to hit a baseball pitched at 90% the speed of light?” or “What if all the water from the oceans were drained?” using real science and mathematical principles (with plenty of wit and cultural references thrown in). According to an interview in The Atlantic, Munroe got the idea for the blog, and subsequently the book, while volunteer-teaching a class for high school students based at MIT about energy. After realizing that his students were particularly excited by hypothetical fictitious scenarios, he started teaching about physics by introducing imaginary cases involving The Lord of the Rings and Star Wars which immediately captured the interest of the students. This “absurd-hypothetical-question-model” method has found a wide audience, and Munroe is credited with spreading scientific interest and excitement to a wider, more popular audience through its use. The “What If” question can thus be a method for teaching and spreading information.
A similar motivation, albeit in a religious context (le-havdil), is at work in the What If series of R. Yitzchok Zilberstein and R. Moshe Sherrow, our third and final work. R. Zilberstein is a colorful contemporary talmid hakham in Israel who has authored numerous sefarim (books) of derush (scriptural exposition), Halakhah, mahshavah (Jewish thought), and more. His multivolume Hashukei Hemed on numerous masekhtot (tractates) of the Talmud discusses halakhic questions that are based (often quite loosely) on each page of the masekhta. These sefarim were originally written to enhance the study of Daf Yomi (a page of Talmud a day) by showing the halakhot that emerge from every page. R. Sherrow then adapted many of these questions (with R. Zilberstein’s answers) and organized them in the order of the weekly parashah (Torah portion). Questions of all sorts abound, from commonplace scenarios (inadvertent damage caused by a workman) to the less common (is an upscale fish tank subject to ayin hara – the evil eye?). Appearing in seven volumes and published by ArtScroll, these books have proven to be very popular and entertaining and have a similar appeal to the works of Rosenfeld and Munroe in capturing the imagination of the reader.
Moreover, the title of the series implies that the book relates questions which are specifically hypothetical, at least in terms of many specific details, as opposed to actual questions posed concerning real halakhic situations. All good teachers recognize the importance of sometimes explaining a given concept by using examples which ignore the practical possibility of the described scenario actually happening, and that is how we might view the methodology of R. Zilberstein’s What If series. But in the original Hebrew editions, there is nothing―neither in the title nor otherwise―to suggest that the questions are at all hypothetical. While a disclaimer indicating that names and other identifying details have been changed does indeed appear, the questions themselves may be assumed to be rooted in reality, as that is how they are presented. Similarly, I could not find anything in the English volumes (where the same disclaimer about name changes is repeated) that would even imply that the questions are anything but real, having been asked regarding actual situations. This stands in stark contrast to the books mentioned above which are clearly and explicitly rooted in fiction. The fact that the Artscroll books are nonetheless entitled “What If” would seem to suggest that the questions therein are at least somewhat divorced from reality and/or may have been edited to reveal an interesting principle, in keeping with the spirit of the pedagogical advantages offered by hypotheticals, or to better arouse interest.
While hypothetical cases already exist throughout the Talmud and appear regularly in traditional rabbinic works down to modern times, the genre of responsa (She’elot u-Teshuvot) has usually been seen as reflecting actual cases where real questions were submitted to a rabbinic authority to be answered and were subsequently made public in a public form. One important exception to this, which we may see as a precedent for the “What If” series, is the Terumat ha-Deshen of R. Israel Isserlein (1390-1460). Containing hundreds of questions and answers, this work was extremely influential among Ashkenazic Jewry and was heavily relied upon by R. Moshe Isserles, who incorporated many of R. Isserlein’s halakhic decisions in his Darkhei Moshe commentary on the Tur and ultimately in his glosses to the Shulhan Arukh.
A somewhat strange tradition about the Terumat ha-Deshen is reported by R. David ben Shmuel ha-Levi (better known as the Taz), R. Shabbatai ha-Kohen (better known as the Shakh), and other rabbinic figures―namely, that the questions recorded there were not really submitted queries but queries invented by R. Isserlein himself, who then proceeded to answer his own question. This tradition was brought into question with the 1903 publishing of the Leket Yosher, a halakhic work by R. Isserlein’s student, R. Joseph (Joselein)―it includes some of the same responsa that appear in the Terumat ha-Deshen but with the names of the individual questioner, thus suggesting that the queries were in fact genuine. More recent scholars, however, have pointed out that these overlaps account for less than a sixth of the total responsa in the original Terumat ha-Deshen, and we should thus not be so quick to discount the traditional view regarding the remainder. Assuming that at least some of the responsa are indeed not based on actual questions posed to R. Isserlein, we can ask why he would create his own halakhic queries. Part of the reason might be the advantage of the format. An imaginary question can serve to sharpen an actual given question, which can then allow for a better, clearer, more comprehensive answer. Consider, for example, the imagined dialogue in R. Yehudah ha-Levi’s Sefer ha-Kuzari, where the Khazar king asks different questions relating to various issues of faith to the hakham (all composed by R. Yehudah ha-Levi himself), or (to a much lesser extent) the imagined exchange upon which Rabbi Samson Raphael Hirsch based his work, The Nineteen Letters. Similarly, Rabbi Aryeh Leib Gunzberg’s Shaagat Aryeh is a halakhic work utilizing a question-answer format with long essays devoted to various issues of Halakhah and lomdut (Jewish learning) and likewise does not represent actual halakhic queries that were sent to him.
The author of the Terumat ha-Deshen, however, may have had a different purpose in mind. In his work on late-medieval Ashkenazic rabbis, Yedidya Dinari marshals evidence from other responsa from that time period to argue that R. Isserlein’s intention was to provide authoritative halakhic responses for use by other rabbis when approached with actual similar situations. It must be remembered that R. Isserlein was writing before the Shulhan Arukh was composed, and while the Tur had already been published and disseminated, there were many situations not dealt with there or those which lacked definitive Ashkenazic pesak (halakhic ruling). The “imagined” questions in the Terumat ha-Deshen therefore served to assist rabbis with the types of real-life halakhic questions that they would be getting by providing them with something to rely on without having to send their questions to R. Isserlein or anyone else.
If this is true, what emerges is somewhat of a stark contrast between the “What If” questions of R. Zilberstein and the Terumat ha-Deshen. In the front of each volume of the ArtScroll What If series (as well as in the loosely corresponding Hebrew works), there is a disclaimer of sorts telling readers that the answers contained therein are not to be relied upon for practical Halakhah. The declared purpose of the sefer is rather to “inspire people to learn Torah,” and, as the English editor R. Moshe Sherrow writes, the intention is to present a work which families could read and learn together at a Shabbat meal. Thus while the Terumat ha-Deshen’s imagined questions were designed specifically to provide “official” halakhic guidance, R. Zilberstein’s are staunchly not, and his work most likely employs this style as a pedagogical tool on the understanding that it would serve to make Torah principles more interesting and relatable to readers. In this sense, for all the difference in genre between history, science, and Halakhah mentioned above, “What Ifs” at their core primarily serve to create greater appeal to a wider audience.
The interest in “What If” literature goes far beyond the examples presented above. From contemporary politics, to sports, to relationships, even to science, people love to ponder the question “What If.” What I have tried to highlight in this review is the diverse ways in which we conceive this question and how we can use hypothetical reality to better understand our own, perhaps even in the realm of Halakhah.
 “What If” hypotheticals have also enjoyed popularity in recent years in the world of fiction. The recent “What If…” Marvel series on Disney+ (based on the Marvel comic series of the same name) was widely viewed, and a number of successful TV series have as their premise an alternate history revolving around different outcomes of World War II, including The Man in the High Castle and The Plot Against America, both based on earlier books.
 Niall Ferguson, “Introduction” in Virtual History: What Could Have Been, ed. Niall Ferguson (New York: Fall River Press, 2009) 87-89. Emphasis in the original.
 One of the fictional chapters actually does include faux explanatory footnotes, but they are not references to scholarly works like those in the nonfiction chapters (which are printed as endnotes).
 One scholar involved in this work confided in me that he was quite disappointed in the final version of Rosenfeld’s book, as he felt that the inclusion of works of fiction alongside serious historical essays diluted the entire collection.
 It is important to clarify that R. Zilberstein himself also authored a series of sefarim which has halakhic questions and answers based on the weekly parashah entitled Veha’arev Na. Many of these appear in an English translation series with the same name, edited by Rabbi Erez Chazani and published by Feldheim. Feldheim also published a family-version-style series, likewise edited by Chazani, entitled Achas Sha’alti. R. Sherrow’s works, however, purport to be based on the Hashukei Hemed series, which, as mentioned, is ordered based on the masekhtot (though no reference to a particular volume or page is provided).
 I heard from one rabbi that a question that he himself had posed to R. Zilberstein (which was later published) indeed had certain details changed/exaggerated/embellished.
See Shakh on Yoreh Deah, 196:20; Taz on Yoreh Deah, 328:2; Beit Shmuel on Even ha-Ezer, 130:20. See also Hida’s Shem ha-Gedolim, Ma’arekhet Gedolim, No. 402. There are possible halakhic ramifications of this tradition regarding the question as to whether one should analyze the specific language of the questions more carefully, considering that they were written―perhaps more precisely/intentionally―by the rabbinic decisor himself.
 For a historical summary of this kind of writing, see Yaakov Shpigel, Amudim be-Toldot ha-Sefer ha-Ivri: Talmid Orekh (Petah Tikvah: 2019), 258-282.
 The original printed title page of the Shaagat Aryeh work does not actually refer to it as a collection of She’elot u-Teshuvot. Interestingly, the Besamim Rosh, a nineteenth-century collection of responsa accused of being a forgery, was defended against this claim by one rabbinic figure who argued that some of the more far out responsa were in fact based on hypotheticals. See Talya Fishman, “Forging Jewish Memory: Besamim Rosh and the Invention of Pre-Emancipation Jewish Culture,” in Jewish History and Jewish Memory: Essays in Honor of Yosef Hayim Yerushalmi, eds. Elisheva Carlebach, John M. Efron, and David N. Myers (Hanover, NH: Brandeis University Press, 1998), 70-88.
 Yedidya Alter Dinari, Hakhmei Ashkenaz be-Shilhei Yemei ha-Benayim (Jerusalem: Mosad Byalik, 1984), 300-310. Dinari also notes the relatively straightforward nature of the questions in the Terumat ha-Deshen, questions which are clearly written with limited external details, and how they do not run across multiple simanim (topics) in the work (as is common with other medieval responsa).
 This is certainly a worthy purpose. The anonymous author of the Sefer ha-Hinukh similarly framed his work, in his introduction, as one that could be used for Torah study and inspiration on Shabbat.