There are two different accounts in the Torah about the wilderness generation. In one, they are doomed to die in the desert for their lack of faith in God. In the other, they use the forty years of wandering to prepare themselves to enter the land. The Torah ultimately sides with the former story. Why? How might Judaism look different if we told of a generation of slaves who themselves, after a period of waiting, entered the promised land?
Here’s the story we usually hear:
God freed the Israelites from slavery, and Moses led them to the edge of the Promised Land. When the scouts reported that both the produce and the people of the land were giant, the Hebrews lost faith in God. They cried, “It is out of hatred for us that the Eternal brought us out of the land of Egypt, to hand us over to the Amorites to wipe us out!” (Deut. 1:27). To punish them, God decreed, “Not one of this wicked generation shall see the good land I swore to give to [their] ancestors!” (Deut. 1:35). Thirty-eight years later, a new generation stood ready to enter Canaan, with Joshua—not Moses—in the lead.
But there’s another story we don’t usually hear, buried deep within the text. The details are all there in the Torah, but they’re eclipsed by the more familiar tale. It goes something like this:
God freed the Israelites from slavery but wasn’t yet sure that they were ready for freedom. And so, God made them walk forty years in the wilderness לָדַעַת אֶת־אֲשֶׁר בִּלְבָבְךָ, “In order to know what was in [their] hearts” (Deut. 8:2), to determine whether they would be able to keep the commandments in the land of promise. During that time, God protected the Israelites and kept them comfortable—clothing intact and feet forever strong (Deut. 8:4). The laws they lived by were the Ten Commandments personally delivered to them at Horeb (also known as Sinai) (Deut. 5:19). Finally, when God brought the Hebrews to the edge of Canaan, Moses conveyed to them, “See, I am teaching you the laws and the rules that the Eternal my God commanded me לַעֲשׂוֹת כֵּן בְּקֶרֶב הָאָרֶץ, for you to abide by in the land you are about to enter and occupy” (Deut. 4:5). This generation—the same generation that fled from Egypt and heard the Ten Commandments—is the one to whom Moses addresses the laws of Deuteronomy so that they may follow them upon taking their place in the Promised Land, and it is this generation that Joshua leads into Canaan.
In the first story, the more common story, the Hebrews who experienced slavery in Egypt were unable to embrace freedom in Canaan. A generation had to pass before they were ready to be free, and Moses was bound to their fate. As he says in this week’s parashah: “Because of you, the Eternal was incensed with me also, saying: Neither shall you, [Moses] enter [the land]” (Deut. 1:37). In the second story, in contrast, the Israelites do need a period of transition between slavery and freedom; but in the end, they themselves get to pass into the land. Now what about Moses in this story? He was simply too old to go with them, as he says: “I am now one hundred and twenty years old. I can no longer lead you” (Deut. 31:2).
Both of these stories are in the Torah. They represent different strands of our textual tradition, different voices or sources that make up our holiest text. But only one of them prevails, leading us to ask: how might Judaism have evolved differently if history had gone another way? What might be the impact on our values and traditions if the Torah taught us that the conquerors of Canaan were also the ragtag band of former slaves?
First, our story would be one of an extraordinary, perhaps unparalleled, generation of Jews. Consider this passage from later in Deuteronomy (chapter 8) that may mostly harmonize with the Haggadah but with a few lines off-key.
20. And when your child asks you in time to come, saying, “What do the testimonies, and the statutes, and the judgments, mean, which the Eternal our God has commanded you?”
21. Then you shall say to your child, “We were Pharaoh’s slaves in Egypt; and the Eternal brought us out of Egypt with a mighty hand;
22. And the Eternal showed signs and wonders, great and grievous, upon Egypt, upon Pharaoh, and upon all his household, before our eyes;
23. And God brought us out from there to bring us in, to give us the land which God swore to our ancestors.”
Here, the purpose and meaning of the exodus is restricted to the exceptional generation it happened to. That generation was historically significant and utterly unique, and it was their experience that merited Israel to receive God’s mitzvot. In other words, that generation was special, even, you might say, Abrahamic—completely unlike our own in character and experience. We need not live up to their example, but they are an example nonetheless, a shining light in the dark recesses of the past.
Additionally, the redemption from slavery of this marvelous generation was merely a necessary step in the relocation of Israel to its rightful land. The exodus was not so much about the value of freedom per se; rather, God simply needed to free those people so that later people could follow the commandments. The mitzvot, not deliverance itself, take center stage. Freedom is secondary to loving God and walking in God’s ways, which are the ultimate fulfillment of a meaningful Jewish life.
And finally, we might learn from this alternate story that tremendous, life-altering, totally transformational change can take place within a single lifetime. Yes, this generation of former slaves needed instruction and chastisement; but in the end, they made it! It is possible—or at least it was for them—to undergo a total paradigm shift over the course of a just few decades.
Now, these are all great lessons, and the narrative is fitting as one of the building blocks of Torah. It makes for a great story! But it’s not the final word. The full version of our mythic history insists instead that there was a changing of the guard between the exodus from Egypt and entrance into Canaan – and this essential difference leads us in distinct moral directions.
For instance, the generation of the exodus and the generation that followed were both heirs to God’s promise, were both beholden to God’s laws, and—most importantly—both felt liberation from slavery with immanence and immediacy. This is the magic of the exodus: You didn’t have to be there to feel its power. Thus the commandment of the tzitzit: “Instruct the Israelites to make fringes on the corners of their garments לְדֹרֹתָם, throughout their generations. … Look at it and recall: … I, the Eternal, am your God אֲשֶׁר הוֹצֵאתִי אֶתְכֶם, who brought you out of the land of Egypt to be your God” (Num. 15:37-41, excerpted). You: Whether you built Pharaoh’s cities or your parents did, whether you are a distant ancestor of those who were enslaved or one who has joined our people through conversion. All are included; all are freed.
The story of generation change in the wilderness teaches us another lesson as well. Big change can happen all at once, but we need new leaders to make a new world in new conditions. We’re setting ourselves up for failure if we think we can build, inhabit, and lead a new world on our own. That is why וְשִׁנַּנְתָּם לְבָנֶיךָ, we must “teach diligently to [our] children” (Deut. 6:7) the values we hold most dear while encouraging them to take the next steps to horizons we can’t reach. The story of generation change is more realistic and, perhaps, more comforting as well than one that says one generation can do it all.
Consider: Parashat D’varim, the beginning of the book of Deuteronomy, always corresponds with the Shabbat before Tisha B’av. And the Shabbat after Tisha B’av is the first of seven weeks of consolation that lead us to Rosh Hashanah. This week’s Torah portion, then, is the first signal that a new year is approaching. Like Moses reflecting on four decades in the wilderness, we also look back on the paths we’ve traveled to reach this spot in our lives. And perhaps, like Moses, we may feel disappointment. Great achievement, of course, for having come this far, but also sadness for falling short of our ultimate goals.
The story we found hidden in the Torah, the story that suggests that great success can come in a single lifetime, might leave us feeling unsettled at such a time. After all, in that story, nearly everyone but Moses gets to build a home in the new land; and we may feel unsatisfied that we could not follow in their footsteps.
But the Torah’s final word comes as one of reassurance. You come as far as you can, you do the best with the circumstances you have, and you strive to prepare the next generation to go where you can only dream. This is the cycle of redemption and the foundation of divine covenant: to be surrounded on all sides by people trying to live up to the principles of holiness passed down to us through the centuries and to do our best to be among their number.
The Torah’s brilliance shines most brightly when we can see its filaments side by side. We know that there is merit in all of them, and yet each generation of Jews, including our own, embraces the stories that best reflect the moral, spiritual, and communal conscience of the day. When we explore the Torah’s depths in search of new ways to apply ancient wisdom in modern times, we’re doing exactly what the text wants us to do.
And so it is with the mythic history of our people in the wilderness. Whether they were there for one generation or two, our scripture allows us to walk alongside them, to learn with them and from them, and to imagine our own lives in their sandals, which, we may recall, never wore out.
As we begin to contemplate the new year, may we all find new meaning in old questions—and may we take comfort and even inspiration in knowing that one generation follows another, reading the stories of our people with new and ever-different eyes.
 See Raanan Eichler’s “The Torah’s Three Explanations for Why Moses Does Not Enter the Land,” https://www.thetorah.com/article/the-torahs-three-explanations-for-why-moses-does-not-enter-the-land.
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