VaYishlach: Holding on Until Dawn
Vayishlach invites us into one of the most raw and vulnerable moments in the story of Jacob: his reencounter with Esav, the brother he deceived and fled from so many years ago. It’s a moment fraught with tension, ambiguity, fear, and the aching hope for reconciliation. As we read this portion during the month of Kislev, a month that culminates in Chanukah and its growing light, it feels particularly appropriate to reflect on what it means to nurture hope in the face of long-standing pain and division.
Jacob’s journey resonates deeply. He emerges from a family marked by dysfunction and distrust, carrying the wounds of a fractured relationship with his brother. How familiar does that feel? In this portion, we see Jacob preparing to meet Esav again — an encounter he approaches with trepidation, dividing his camp in fear of what might come. Yet, before he faces his brother, he finds himself wrestling, alone in the night.
Who does Jacob wrestle with? The text is ambiguous, offering no clear answers. Is it an angel? The spirit of Esav? Or is Jacob wrestling with himself, his own guilt and fear? The ambiguity in the text mirrors the ambiguity in our own struggles. The Hebrew word for “wrestle,” vaye’avek, carries within it the root for “dust” (avak), suggesting a kicking up of dust — a blurring of boundaries between adversaries. Who is Jacob fighting, and who is winning? The Torah doesn’t tell us, and maybe that’s the point. Sometimes our most profound struggles are not about victory but about holding on until dawn breaks.
And then, the moment comes: Jacob and Esav meet. The text tells us, “Esav ran to greet him. He embraced him, fell on his neck, kissed him, and they wept” (Genesis 33:4). The pronouns blur here, too — who is embracing whom, who is weeping? Above the word for “kissed” (vayishakehu), the Torah places mysterious dots. Some traditions suggest Esav’s kiss was insincere, that his heart remained cold. Others say his heart melted in that moment, that the act of embracing his brother softened the years of anger. Regardless of interpretation, the text holds space for ambiguity — for the possibility of genuine connection even amidst unresolved pain.
This story does not end with sustained reconciliation. Jacob and Esav do not travel together after this moment; their paths ultimately diverge again. And yet, there is something profoundly hopeful about that fleeting embrace. It doesn’t erase the past or promise a simpler future, but it reminds us that even the deepest estrangements carry within them the possibility of a moment of connection, however brief.
As we light the Chanukah candles in the coming weeks, placing them in our windows to pierce the darkness, I find myself reflecting on the kind of darkness that exists within families, within communities, between tribes, between people. The story of Jacob and Esav reminds us to dream of light even there. It reminds us that, despite everything, a moment of embrace is possible — a moment of shared humanity that transcends even the most profound and painful divisions, please God.
I don’t know if we can fully reunite with those from whom we’ve been estranged. Maybe such moments are ephemeral, fleeting glimpses of what could be but isn’t yet sustainable. Still, I find myself dreaming of what it would feel like to hug, to weep, to melt hearts. And I find myself praying: for the return of hostages, for the mending of family ties, for the day when we might truly see each other again — not as adversaries but as siblings. Maybe the concept of peace. Maybe. Someday. Please.
May this month Kislev bring light to our fractured world. And may we be blessed, one day, to experience the kind of embrace that Jacob and Esav shared — a moment of connection that reminds us we are still capable of dreaming, still capable of hope.