Letter and Spirit: Evasion, Avoidance and Workarounds in the Halakhic System 

By Rabbi Daniel Z. Feldman 

Maggid Books 

Jerusalem 2024 

327 pages 

Reviewed by Rabbi Moshe Kurtz 

One of my heuristics for initially evaluating a work—and one can debate whether it is a fair metric—is to scan through the footnotes and citations contained therein. The author should be able to demonstrate that he has done his homework. Rarely have I been so overawed by the sheer breadth and depth of research in a book as I have been by Rabbi Daniel Feldman’s Letter and Spirit: Evasion, Avoidance and Workarounds in the Halakhic System.  

One might be tempted to describe Letter and Spirit as a collection of case studies in ha’aramot (circumventions in the halachic system). But I can imagine Rabbi Feldman heaving a sigh of exasperation at such a characterization. He begins the book by noting that simply defining the term ha’aramah—the entire theme of the book—is already a fraught endeavor: 

The subject at hand is one which, in a sense, cannot be named. To name it is to judge it, both collectively and in its parts, and therein lies the challenge that is to be addressed. Terms such as “evasions” or “workarounds” label the user as derelict in responsibility, deficient in commitment, perhaps even on some level dishonest. Similarly, or more so, “subterfuge,” defined as “deceit used in order to achieve one’s goal.” Even worse are terms such as “loophole,” which implies both an oversight by the system—a near-heretical implication when applied to the Divine Torah—and exploitation on the part of the user; or “legal fiction,” which imputes insincerity to both sides. Perhaps some of these negative impressions are justified, perhaps not; either way, usage of these terms prejudges the question and undercuts the investigation before us (Introduction, p. xxi). 

Readers have likely pondered both the efficacy and ethics behind a mass sale of chametz prior to Pesach, when the Torah explicitly commands us to destroy it—“tashbitu” (Exodus 12:15). If we have either drafted a will or been bequeathed a family member’s inheritance, we may have wondered how daughters can receive an equivalent allotment to their brothers, despite the Torah strictly prioritizing the sons. And if we have ever arranged a loan with another Jewish entity, we may have utilized a heter iska in order to obviate the proscription against charging a fellow Jew interest.  

Workarounds such as the sale of chametz, the shtar zachar shalem for inheritance, and the heter iska for borrowing with interest have engendered a degree of skepticism, and for some, even cynicism, toward the halachic system. A common claim advanced is that if Hillel and the rabbinic establishment could concoct a prozbul document to prevent the dissolution of debt in the seventh year (shemitat kesafim), how is it remotely conscionable that they could not devise a similarly creative method to free countless agunot, women who are chained in functionally dead marriages. It certainly stands to reason that an individual’s ability to obtain a divorce and start the next chapter of her life should take priority over saving someone from disposing his Cinnamon Toast Crunch cereal before Pesach or enabling a barbecue during the Nine Days.  

Rather than simply throwing several disjointed case studies in ha’aramot at us, Rabbi Feldman introduces his own working theory to demonstrate that there is indeed an underlying method to the application of these workarounds. The key conceptual contribution of the book, or chiddush if you will, is his application of a four-point questionnaire of criteria for assessing the propriety of a proposed workaround: (A) Does it accord with the letter of the law? (B) Does it accord with the spirit of the law? (C) Is the workaround being enacted sincerely, e.g., are the buyer and seller implementing an effective sale? (D) What is the level of need or urgency? He amusingly illustrates this by writing: 

It has been joked that the rabbis have prohibited smoking, but still the Orthodox Jews are not concerned; they will simply sell their lungs to a non-Jew. This joke represents a failure of both parts (B) and (C): selling one’s lungs to another would do nothing to protect the seller from the harm of the cigarette smoke; and it would be no kind of a sale, as the lungs would remain in the body and under the active use of the seller (p. 24). 

Workarounds such as the sale of chametz, the shtar zachar shalem for inheritance, and the heter iska for borrowing with interest have engendered a degree of skepticism, and for some, even cynicism, toward the halachic system. 

In every instance of potential ha’aramah, the halachic authorities, either consciously or intuitively, balance these four factors. A significant technical hurdle is more likely to be finessed when there is an overriding spirit of the law factor or exigent circumstances at play. It may even be two bona fide Jewish values competing with one another. For instance, the impetus for both prozbul and heter iska can be understood as the enabling of loans to ensure economic opportunities for those possessing lesser financial means. To take an uncompromising letter-of-the-law position would practically result in zero loans, rather than loans that adhere to the prescribed parameters of Biblical law. When I had the opportunity to interview Rabbi Feldman on my podcast, Shu”T First, Ask Questions Later, he confirmed my suspicion that indeed the sequencing of the chapters in the book was not merely chronological but purposeful and pedagogical. The treatments of various case studies of ha’aramot throughout the ages equip the reader to then engage with the more modern and pressing issues of cases like igun (the state of being chained), which is addressed toward the conclusion of the book. This chapter in particular draws upon figures within the Yeshiva University/RIETS orbit who have largely been staunch proponents of the Beth Din of America’s Halachic Prenuptial Agreement.  

I particularly appreciated Rabbi Feldman’s integration of both his rebbeim and colleagues alike, including Rabbi Daniel Rapp, Rabbi Yona Reiss, Rabbi Menachem Genack, Rabbi Aharon Lichtenstein, Rabbi J. David Bleich, and, of course, Rabbi Joseph B. Soloveitchik. I found his citation of Rabbi Hershel Schachter’s treatment in B’Ikvei HaTzon (15:1) about the sale of chametz to be particularly enlightening. Rabbi Schachter distinguishes between the circumvention of a positive commandment and a negative commandment, positing that it is generally problematic to circumvent a positive commandment but not a negative one. It follows that the sale of chametz is not a problematic ha’aramah as long as it merely obviates the transgression of possessing chametz on Pesach (bal yera’eh u’bal yimatzei), while still enabling the individual to proactively fulfill his positive mitzvah of destroying a small portion of chametz on the morning before Pesach. 

It is not surprising that this book was published by the RIETS Press of Yeshiva University, as Rabbi Feldman serves as its distinguished executive editor. What did raise an eyebrow, however, was that this work was classified under the “RIETS Hashkafah Series” rather than as part of the halachic genre. Years of studying Brisker lomdut sensitizes one to inquire what the Rambam is conveying by his sequencing of laws in his Mishneh Torah. In a similar fashion, my radar was alerted by this intriguing categorization. 

The likely explanation is that this book does not actually dispense any practical conclusions such as a typical halachic digest would be expected to provide. While the book’s content primarily emerges from halachic literature, it is in service of propounding particular philosophical messages, such as combating cynicism toward the halachic process, which Rabbi Feldman describes as “corrosive to the soul and damaging to the commitment needed to bring the Divine word to life” (p. 233).  

As this book emerges from the world of Torah Umadda, I was anticipating a broader academic tie in. I deeply appreciated Rabbi Feldman’s analogy to tax avoidance versus tax evasion. He points to an example attributed to the early twentieth-century Supreme Court Justice Louis D. Brandeis, who explained that avoiding a toll road is completely legal while taking the toll route and evading payment would be illegal (pp. 15–16). Additional examples like this throughout the book would have further enhanced what is already an exceedingly edifying experience. Though, as I prefaced, the sheer volume of citations in this book already makes it a force to be reckoned with; perhaps more would be akin to an excess of blessing (see Ta’anit 9a). 

Rabbi Feldman’s insistence on a more charitable understanding of ha’aramot reminds us to place our understanding of mitzvot in a positive framework. Rabbi Moshe Feinstein (Iggerot Moshe, YD 2:16) was asked about the propriety of a shochet wearing gloves when performing the mitzvah of shechitah. He replied that it depended on the reasoning: To protect one’s hands against the cold is one matter, but to protect one’s hands from a mitzvah is unconscionable. He remarked that a person needs to perform a mitzvah “with joy and love, and should be honored by the opportunity to soil his hands for the sake of a mitzvah, and not find workarounds to avoid dirtying himself.” While halachah employs ha’aramot in limited circumstances, our general orientation toward Torah observance should be to seize every mitzvah as an opportunity and privilege. “Ki heim chayeinu v’orech yameinu—For they are our life and the length of our days.”   

Rabbi Moshe Kurtz serves as the rabbi of Congregation Sons of Israel in Allentown, Pennsylvania. He is the author of Challenging Assumptions (Beit Shemesh, Israel, 2023) and hosts the Shu”T First, Ask Questions Later podcast. He writes a regular column called “Unpacking the Iggerot” for TraditionOnline and, G-d willing, will be releasing Meoros Moshe, a Hebrew anthology of Rav Moshe Feinstein on Pirkei Avot.