Genesis 32:17 tells us, "And he placed them in the hands of his slaves, each flock separately, and he told them: Go before me, and leave space between the flocks." Jacob isn't just sending a gift; he’s orchestrating a whole performance.

Why this elaborate dance? Why not just send one big honking herd of livestock?

Our Sages, in Bereshit Rabbah, that treasure trove of rabbinic interpretations, delve deep into Jacob's motivations. "He commanded the first, saying: When Esau my brother meets you, and asks you, saying: To whom do you belong, and where are you going, and whose are these before you? You shall say: They are from your servant, Jacob; it is a gift sent to my lord, to Esau and, behold, he too, is behind us" (Genesis 32:18-19).

Notice the careful wording. Jacob calls himself Esau’s servant, a move that seems, well, a little subservient, doesn’t it? The text goes on to say, "He commanded also the second, and also the third, and also all that followed the droves, saying: In this manner shall you speak to Esau, when you find him” (Genesis 32:20). He’s leaving nothing to chance.

There's a fascinating anecdote in Bereshit Rabbah involving Rabbi Yehuda HaNasi and Rabbi Yosei ben Rabbi Yehuda. They were walking when they saw a gentile approaching, and anticipated being asked three questions: "What are you? What is your trade? Where are you going?" The rabbis prepared themselves, recognizing the need for consistent answers, much like Jacob prepping his messengers. Rabbi Yosei worried that if he didn’t hear Rabbi Yehuda’s answer first, his own might contradict, arousing suspicion. What can we learn from this? Jacob prepared his messengers for all contingencies.

Rabbi Pinchas and Rabbi Hilkiya, quoting Rabbi Simon, offer another layer. They suggest that Jacob's instructions were contingent on Esau's status. "When you find him," they say, "in his greatness." But if he is no longer in his greatness, approach him differently. It was in order to astonish him with his gift.

Isn't that insightful? Jacob wasn't just being obsequious; he was assessing the situation and tailoring his approach accordingly.

But why the separate flocks? Bereshit Rabbah explains that Jacob wanted to "astonish him with his gift," to impress Esau with the sheer variety and abundance. But there was another reason: "It was in order to satiate the eyes of the wicked one." He came to end it, but he said: ‘Receive’; He came to end it, but he said: ‘Receive.’ Each time Esau thought that the gift was complete, Jacob’s servant would say: There is more for you to receive. Jacob understood that dealing with someone like Esau required a strategic approach, a kind of psychological manipulation.

Now, here's where it gets a little uncomfortable. The text quotes Job 9:24: "The earth is given into the hand of the wicked one; he covers the faces of its judges…" This verse is brought in connection to Jacob calling himself Esau’s servant. It raises the question: Is Jacob compromising his integrity by appeasing Esau? Is he acknowledging Esau’s power, even if it's unjust?

The final verse quoted, referencing Genesis 32:22, notes that "The gift went before him [al panav]" and connects the word panav, "before him," with distress. Even as he sent the gifts, Jacob himself was troubled.

So, what do we take away from this intricate portrait of Jacob's preparations?

It's a reminder that navigating complex relationships, especially those with power imbalances, often requires careful planning and, sometimes, uncomfortable compromises. It forces us to confront the ethical dilemmas that arise when dealing with difficult people. When do we stand our ground, and when do we try to appease? Jacob’s story doesn't offer easy answers, but it does provide a powerful example of strategic thinking, emotional intelligence, and the enduring human struggle to find peace, even when it means walking on eggshells.