This week’s Torah segment begins with Moshe (Moses) telling of his his failed attempts to persuade God to let him enter the land of Canaan. “Va’ethanan, And I beseeched the Lord at that time, saying…”. The Midrash reads a lesson about prayer from each word in this verse.

For example, the unusual first term, Va’ethanan, which contains the root ch-n-n, is linked to the similar root, chinam, which translates as gratis, free of charge.. From this word play, the early midrash known as Sifri, quoted by Rashi, teaches

“it is in the language of a free gift, for while the righteous could fall back on their good deeds, the righteous ask that Gd grant them their request as a free gift…”.

In other words, true prayer is not a negotiation with God, in which one reminds God of one’s merits and requests fulfillment as a tit-for tat, rather, when one asks something of God it should be from a place of emptiness, as though one had no merits at all.

The Tiferet Shelomo points out that negotiating on the basis of merit is a dangerous exercise, for there is no person without sin; the risk is, that invoking merit may also resurrect the old skeleton in the closet…

The Kotzker states that no righteous person falls back on their merits because no truly righteous person actually would think of themselves as possessing merit; the only ‘merit’ they may be willing to invoke is their willingness to strive for merit in the future, but even this in their own eyes is deficient.

In short, the classical Hasidic approach to prayer emanates from an acceptance of the human condition as tragic, a tragic condition that not even the greatest spiritual hero is capable of transcending.

And that brings us back to the context of this verse, for after all, of all the places in the Torah that once can learn lessons about prayer, the choice of this perasha is an odd one, since the prayer here is a failed prayer. Moshe asks rather persistently to enter the land (the mystics say that Moshe prayed 515 different prayers, “taktu tefillot”, corresponding to the numerical value of the term “va’ethanan”), and yet, God says “no“. If anything, one would think that this perasha was an instructive admonition in how not to pray…

I’d like to suggest that perhaps the failure is the message. Prayer is about something other than getting one’s wish fulfilled. Prayer is a vehicle for personal transformation, and almost requires recognition of the inability to get all that one wants all of the time.

Prayer may fail at so many points- for example, one may not even be able to pray. R. Nachman of Breslov in Likutei Moharan 99, reads this lesson from our verse: Va’ethanan el Hashem- Pray to God even when you know that your attempt at prayer will be a failure, so that “be’et hahi“, when you do reach the appropriate spiritual level of devekut, of cleaving unto Gd, then “laymor“, then your prayers will themselves speak, so to speak, they themselves will “laymor” and elevate all the previous, failed prayers, along with them.

To R. Zadok Hacohen and the Sefat Emet the human situation of inadequacy, with redemption and growth coming through prayer, is at the core of this entire perasha. R. Zadok points out that this segue into the next few verses is puzzling. Moshe begins the narrative with his own failure in swaying God to allow him to enter the land, and then, in 4:1, proceeds: And now, Israel, hearken unto the statutes and laws that I will teach you so that you live and inherit the land, etc.

How can Moshe, who failed to gain entry to the land, be setting down the way to live life in the new land? And why is this connected textually to his failure at prayer?

According to R. Zadok, Moshe understood why he failed in his prayer, and why he could not enter the land. He understood the “flaw” was with himself- he was too great a man. A man who had achieved this great a level, who was so distant from sin and temptation (a man and a generation – the Ohr HaChayim points out that Moshe’s failure parallels that of the entire Dor Hamidbar, the generation he led through the desert, the generation which had witnessed Sinai), was not the person who could teach the most important lesson for the new Jewish society about to unfold, the lesson of Teshuva, repentance. He citess various prooftexts, from the BT Rosh Hashana, for example, to make this point, but even a common sense reflection makes this argument compelling. Essentially, there are people who are not allowed to make mistakes. While the lesson of teshuva is that all humans are fallible, thus a mechanism whereby the individual and society can overcome mistakes is necessary, still, there are classes of people from whom this lesson is invalid, and from whom apologies would not be repugnant.

For example, no one would allow a physician the leeway for error that might lead to a patient’s death, and “repenting” for it would be an absurdity. This would hold true for leaders in whom one appoints to ensure the protection of a society. “Oops, I’m sorry, it was a mistake” is not an acceptable position for a leader whose country had been destroyed.

Moshe who received Torah from God is not allowed to make critical mistakes of this sort and learn lessons from them. That is a not a privilege granted to individuals of that caliber, in that position of responsibility.

The Sefat Emet also understands that growth and potential is not valid in every case. Moshe (and his generation) could not change, because he was the representative of Torah Shebichtav, the immutable Written Law, which needed to be fixed and protected in an inalterable fashion. A written text is not one that “grows” within itself, it must remain as it is, in order that it may continue to instruct, and serve as an archetype.

Society, however, the new life in the new land, an organic evolving society needs to be defined as Torah Sheb’al Peh, the Oral Law, as a vital commentary on the fixed Written Law, a commentary which grows out of the challenges a faces as it grows naturally, and the lessons it learns as it encounters these problems.

The Sefat Emet notes from this dichotomy, that the role of the Oral Law must be to foment the perfection of human society from the perspectives of justice, fairness and equality. The prototypical example is the case presented by the daughters of Zelophad, who questioned a potential injustice in the received law, and led to the law’s revision, with divine acquiesence. This is the role of society in the new land, and the role of the oral law as the process by which an ideal, just, humane society, continually striving for self perfection is created. This growth is not an option for Moshe and his Generation of the Desert.

In one of his letters, Franz Kafka reflected upon this type of dichotomy between fixed word and fluid action as it might apply to himself as a new society was in the process of being formed. In his letter of Jan 28, 1922, Kafka agonizes over joining the Zionist movement, and he refers to his situation as being “something like wandering the desert in reverse”. Living in the land might force him to become a settled member of society, as opposed to his current state of

“wilderness- an organization according to which…there are elevations at lightning speeds, and also, of course, crushing moments that last thousands of years as if under the weight of the seas”.

This state of “wilderness” is an appropriate description of the desert generation which experienced heights of Sinai followed by the cataclysmic fall of the Golden Calf. One must be special to reach such elevations and to fall to such depths, it is not the kind of swing that would be possible in a normal society. A generation of such profound experience cannot be the ones to create a new society tolerant of the normal human foibles; the range is too broad and the spectrum of responsibility beyond the capacity for ordinary human sensitivity.

Thus, Moshe and his generation were not the ones to live the stable lives of society and law, and for that reason, to some extent, we might say that they lived outside of the world of Tefilla, of prayer. Thus the reply of God to their prayer as stated in the text: Rav lach, you are beyond this. And this is why in the very next passage Moshe says (4:1) And now, O Israel, listen to the laws and statutes which I will teach you to do, so that you may live in the land… He is saying, you will do these things that I will teach, which I can’t do, because I am too tied to that desert, and not someone who can build up a normal healthy functioning society based on law and justice.

The Midrash Devarim Rabba 2:9 states that Moshe could not enter the land because in death as well as life he was one with his generation, and at the end of days, he will march at their head and bring the revived desert generation into Israel. Perhaps this is meant to suggest that once a functioning just society is truly actualized, with the eradication of all social inequity and societal injustice, that is, with the achievement of true tikkun olam, symbolized in traditional texts by the arrival of the messiah and the end of history, at that point a healthy society will be ready to reintroduce the spirit of the desert, and be ready to integrate their message of creative instability in a constructive manner.

In the meantime, society requires the approach built upon Moshe’s failure. Prayer and spiritual leadership must not be the coming of a Zarathusra out of the desert who perceives himself or herself as being personally superior, that is, arguing for leadership because he has “great merit before the Lord”. The Yismach Yisrael riffs off the Midrash in Devarim Rabba 2:6, in which the plural phrase laymor, saying, is instructive of the appropriate route for prayer. Prayer, he explains, is effective when it is a reflection of the wishes of a society coming before Gd. One prays recognizing that one is a human with social ties and responsibilities. One does not pray in the desert, one should pray recognizing the human condition, and one’s condition as a part of all of humanity. The Tiferet Shelomo rejected the route of solitude and requested that his disciples come to him even with their “mere” daily needs, so that he would continuously be reminded of the travails of mundane daily life, and not perceive his isolated spiritual existence as being representative of existence.

It is for this reason that traditional Jewish prayers are always voiced in the plural. Look carefully at the Viddui prayer, the central confessional prayer repeated multiple times during the Yom Kippur services. The sins listed (ashamnu, bagadnu, etc.) are all enumerated in the plural form, and even the most righteous person recites the list of failures, personal merit does not exempt one from being a part of this service. Why? R. Haim Vital, in the Shaar Hakavanot, explains that even if one hasn’t violated one or the other specific sin, one must aware by definition, in society, not all are perfect, and someone might have fallen and be in need of prayer. Even a great spiritual hero like Moshe has the capacity for failure, the potential for failure and redemption is at the core of our existence as humans in society, and our prayers are meant to be for the transformation of all within an ever more just and equal society.

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