Vayishlach
Genesis 32:4 – 36:43 

By Jen Smith  

Parshat Vayishlach opens with Jacob preparing for one of the most emotionally charged encounters in the Torah: meeting his estranged brother Esau after twenty years. This is not a simple reunion – it is a confrontation with fear, guilt, memory, family history, and the shadows of old wounds. Jacob is terrified. Esau is unpredictable. And the Torah, in its brilliance, holds open the ambiguity: What happens when the people we share blood with are not the people we feel safest with? 

Before Jacob can face Esau, he must face himself. 

On the banks of the Yabbok, Jacob wrestles an unknown being: an angel, a man, his brother’s guardian, or perhaps the shadow-self he has been running from his whole life. Jewish mysticism teaches that this struggle represents mochin d’gadlut, expanding consciousness, when a person moves through constriction (fear, ego, old hurts) and emerges with a new name, a new sense of self, and a new capacity to act differently. 

Jacob receives the name Israel, meaning “the one who wrestles with God,” but he is also left with a physical reminder of his encounter with the divine. Jacob’s limp becomes a physical reminder that profound transformation rarely leaves us untouched, and yet, Jacob limps toward reconciliation anyway, something we all know to be true: with growth often comes a painful cost. 

This time of year, whether around Thanksgiving tables, Hanukkah celebrations, or just winter holidays – many of us prepare, Jacob-like, to meet family members who bring out our best, our worst, or simply our weariness. We strategize seating charts. We rehearse conversations. We pray no one brings up politics, Israel, that thing someone said last year, or any other emotional landmine. 

Our world is polarized, grieving, anxious, and loud. Conversations about Israel, antisemitism, identity, politics, and Jewish life carry immense emotional weight right now. Even those we love may not see the world as we do. Some family members feel like Esau: unpredictable, intense, carrying their own hurts and judgments. And what about us? We are often more like Jacob than we admit: scared, defensive, and bracing for impact. 

Vayishlach whispers an uncomfortable but liberating truth: We meet others as we are, not as they are. And so, the work begins long before we even arrive at the table. 

Jacob sends gifts ahead of his arrival as an offering of tikkun (repair) as a gesture to soften what has hardened. We, too, can send our own gifts: patience, a pause before reacting, curiosity instead of accusation, boundaries that are firm but not cruel, and compassion that does not demand agreement. 

After the reunion, with Esau running and Jacob weeping, Jacob tells his brother: To see your face is like seeing the face of God. (Genesis 33:10) 

What a radical and mystical statement! The Baal Shem Tov taught that the Divine often appears in moments of courage and vulnerability, especially when we choose connection over fear. Even if the relationship is imperfect. Even if reconciliation is temporary. And even if the embrace is followed by separation. 

Judaism does not demand we like everyone, not even family. But it does challenge us to recognize the spark of the Divine in the person sitting across from us, and to know that it does not diminish ours. Seeing God in another doesn’t require agreement. It requires presence. 

In a year where Israel is on our minds and hearts, where antisemitism rises, where Jewish identity feels both precious and embattled, family disagreements can feel amplified. But Vayishlach reminds us that sacred encounters often emerge in tense spaces. 

And the reunion is real – not because it resolves everything, but because it honors the possibility of healing even when history is complicated. That is a profoundly Jewish value. 

This Torah portion invites us to conduct our inner wrestling before engaging in outer conversation, hold our boundaries with compassion, show up as our transformed selves rather than our triggered selves, and believe in small moments of reconciliation (even if they are temporary) as holy. 

During holiday gatherings, we can emulate Jacob by approaching family with both honesty and softness as well as courage and humility. Far from a lofty pursuit of perfection, this goal is about presence. We, like Jacob, may not walk away unchanged, but the resulting limp can be a blessing reminding us that all relationships worth having require effort, courage, and periodic discomfort. 

And sometimes, if we are lucky, there may even be an embrace. 

Shabbat Shalom.