Ah, the benefits of Google and, more recently, of AI. For, you see, I have long had a special interest in the saying, “Be careful what you pray for lest it come true.” I attributed this advice to the British playwright, George Bernard Shaw.

As I hope to demonstrate in this week’s column, there is much to support Shaw’s counsel in traditional Jewish sources. But I wanted to first ascertain the true author of those words. Was it really this famous but non-Jewish sceptic, or could I find some other wise individual who said something similar. And, especially, could I find authoritative Jewish sources that promulgated a similar approach to prayer?

I began, as I often do, by consulting Google and AI. I immediately discovered that I needed to abandon my assumption that the source of the saying was George Bernard Shaw. Nor was it the product of another British literary hero, Oscar Wilde. Rather, it dated back to Aesop’s Fables, circa 260 B.C.

I immediately had an “aha” moment. That date coincided with the Second Temple period and the years of prominence of the Anshei Knesset HaGedolah (the Men of the Great Assembly). Perhaps Aesop’s saying had its origins, or at least some parallels, in Jewish sources dating back to late biblical or early rabbinic times.

But first, permit me to describe the roots of my fascination with the saying. I trace that fascination with the need for cautious prayer back to my high school days. More specifically, to the late spring of my eleventh-grade year at Rabbi Jacob Joseph High School on the Lower East Side of Manhattan.

Like most of my peers, I was preoccupied with finding a summer job, preferably one with at least a modest salary and a location such as the Catskill mountains. Like a good Yeshiva bachur, I incorporated my ardent desires in my three daily prayers. I specified in detail exactly what I was looking for: minimum wage, vacation days so that I could tour the Catskills, opportunities to swim, go boating, play basketball, and friendly companions.

Of course, in my prayers I promised the Almighty that I would gratefully “compensate” Him for answering my prayers by devoting the entire next year, my senior year, to diligent Talmud study, perfect attendance, obedience to my rabbis, and impeccable conformity to every halachic stringency.

Had my prayers come true, I may have had, at most, a pleasant summer. With certainty, I would have wasted a precious summer and gained little spiritual substance.

Suffice it to say that my prayers were unsuccessful. Denied summer employment, I instead accepted an invitation from my eleventh grade rebbe, Rabbi Yitzchak Tendler, of blessed memory, to join a study group at his home during the months of late June and July. The curriculum would focus upon the halachic disputes between two early nineteenth century Talmudic scholars, Rabbi Aryeh Leib HaCohen Heller (author of Ketzos HaChoshen), and Rabbi Yakov Loberbaum (author of Nesivos HaMishpat).

The group met twice a week for six weeks. During that time, we learned that the disputes between these two dazzling scholars were based upon fundamentally different approaches to Talmudic analysis. We were asked to choose which of the two approaches appealed to us acolytes. We were twelve students, as I recall, and we were split evenly between those who advocated the style of the author of Ketzos versus those who favored his opponent, the Nesivos.

I aligned myself with the Nesivos and continue to this very day to study the many other works that he published. One of those works is his commentary on Chumash, entitled Nachalas Yaakov. It is there that I discovered his teaching on a verse in this week’s Torah portion, Ekev (Deuteronomy 7:12-11:25), specifically the verse (ibid. 9:26) which reads, “I prayed to the Lord and said, ‘O Lord G-d, do not annihilate Your very own people, whom You redeemed in Your majesty and whom You freed from Egypt with a mighty hand.’”

Upon this verse, the author of Nesivos cites this Talmudic passage (Berachot 32b): “Anyone who prolongs his prayer is assured that his prayer will not return unanswered. From where do we derive this? From Moses our teacher.” The passage continues to cite the very verse that we just quoted in the previous paragraph! The Talmud continues to inform us of the Lord’s response to Moses’ prolonged prayer: “And the Lord heard me that time as well…”

The Talmud proceeds to question the above teaching: “Is that so? Did not Rabbi Yochanan say that anyone who prolongs his prayer and expects it to be answered will ultimately come to heartache (as it will not be answered), as it is stated: ‘Hope deferred make the heart sick.’ (Proverbs 13:12)?”

The author of Nesivos suggests the following interpretation of the above passage: “‘Prolonging prayer’ in this context refers to one who specifies at length and in detail precisely what he is asking for, and what he is convinced is good for him. But truth to be told, no person really knows what is good for him! It is preferable to recite the standard prescribed prayer or leave it up to the Almighty to determine what is best for him. Thereby he will avoid heartache and demonstrate his trust in the Lord. If one thinks that he knows what is good for himself, and doesn’t achieve the goals of his prayers, that is when he will suffer heartache.”

It is in this passage in his lesser-known work, Nachalas Yaakov, that the author of Nesivos discourages the specification of particular personal requests in one’s prayers.

It must be pointed out, in all fairness, that other authorities disagree. Two examples are offered in the edition of Nachlas Yaakov published by Machon Yerushalayim. One is the is author of Chayei Adam who writes that “it is appropriate for everyone to pray daily for his personal needs and sustenance and for what he knows in his heart is good for him”. The other, an earlier authority, is Rabbi Yonasan Eybeshutz in his Yaaros Devash, book 1, sermon 1.

I dare not intervene between these outstanding authorities, despite my personal affinity with the teachings of Rabbi Yaakov Loberbaum. After all, I discovered him during the summer that my adolescent prayers were denied, but when I was rewarded with a summer of spiritual and intellectual growth and by becoming acquainted with one of my lifelong rabbinic heroes, the author of Nesivos HaMishpat, Nachalas Yakov, and numerous other masterpieces.

I leave it up to you, dear reader, to choose the approach to prayer that appeals to you upon reflection. One way or the other, pray!