Parshat Vayishlach: The Blessing of Choosing to Wrestle

Shabbat Shalom, everyone.

With your permission, I’d like to dive right in this morning. Those of you who have learned with me at Timely Torah know that my biggest lament is that we section off a half-hour of learning rather than the six or so hours that we really need to dive into the text. And all the more so for a Shabbat sermon, where we are tasked to uncover some profound truths together in a 10-15 minute window.

All of that is to say: time is of the essence. So, let’s jump right in.

I want to talk this morning about one of the most iconic and consequential moments in all of Torah: Yaakov’s midnight wrestling as he prepares to reunite with his brother, Esav. This reunion is so filled with uncertainty, loaded with tension and anxiety.

Now, often when a rabbi, Jewish scholar, or educator speaks on this narrative moment, they focus on one particular question: Who is Yaakov wrestling? Is it an angel? Is it Esav? Is it God? Is it some combination of all of these — the wrestling of Yaakov and Esav’s spirits or essences before their physical confrontation the next day? This is the question.

But here’s why I want to jump right in this morning: I think it’s the wrong question.

It’s an interesting question, but it distracts from what I believe is the real focus of this particular story. And here it is — the chidush, the central theological nugget that is built in the text:

Yaakov is willing to wrestle at all.

Now, what do I mean by that? If we rewind and take a look at Yaakov’s story up to this point, we see that his story is built on deception and manipulation. He takes advantage of his brother Esav’s hunger and takes his birthright from him. He deceives his father, Isaac, to receive the blessing of the firstborn. And his 20 years with Lavan, and his eventual departure, are filled with all kinds of meshugas. Everyone is cheating everyone. It’s a mess.

But here is this incredible moment in the Torah where Yaakov prepares to meet his brother. And he does so in a very typical Yaakov way: he makes a plan. He prepares for all kinds of possible outcomes. He divides his family into sections, so that if, chas v’Chalilah, Esav intends to kill him, at least some part of his family and possessions will be saved. That sounds like Yaakov. That’s the Yaakov we know.

But then, God throws a wrench into the whole Yaakov machine.

Separated from everyone, left alone on an elevated plateau where Yaakov himslef had once felt the presence of God, everything is turned upside down. In the middle of the night, an ish — a person, a figure — confronts Yaakov. It holds him in place, preventing him from moving, taking away all his preparation and planning — everything Yaakov depended on for a successful encounter in the morning. This figure challenges him in a way he has never experienced in his life.

I imagine the conversation, if there was one, took place without words. It was, in its essence, a throwing down of the gauntlet before Yaakov. This figure, this ish, seems to say:

You are willing to cheat. You are willing to lie. You are willing to trick and deceive. But are you willing to fight? Are you willing to strip away all of the games, all of the illusions, and confront your destiny head-on — as you, as who you are, alone and vulnerable?

And Yaakov’s answer is yes.

He fights. He strips away the past. He lets go of the narrative that was. He lets go of the past and he wrestles.

And here’s the most important part: as he wrestles, he’s injured.

The ish, realizing that Yaakov has risen to the challenge and will not release him, strikes him in the hip, seemingly dislocating his leg from his hip socket. And still, Yaakov doesn’t let go.

We can imagine this incredibly dramatic moment: Yaakov, with tears in his eyes and his body charged with pain, turns to the figure and says, “No! I’m not going to let you go until you bless me.”

Who is this ish, this midnight wrestler? I don’t think it matters.

Because it doesn’t change the outcome.

This outcome is, by its nature, transformational. And, at least according to the text, it seems this transformation is immediately perceptible to everyone — to Yaakov himself, to his family, to Esav.

Yaakov is changed.

Which changes the way we look at the story. He’s not just given a new name; he’s transformed into a new person entirely. His is a new identity. He becomes Yisrael — the one who is willing to wrestle.

And because Torah means instruction (that’s its literal translation), we know that this story is meant not to just provide us with some entertainment and some plot twists. This story, this transformational wrestling match is meant to teach us something valuable. And I believe that’s exactly what it does.

Built into this message is one of the central tenets of our tradition — of Judaism as a theology and philosophy. And it’s one we, as adults, need to hear.

Why do I say adults? Because children are much better at this than we are.

As we grow older, we become more averse to risk. We approach everything with more caution, more hesitancy, and more skepticism. And while that has its benefits. It is not a bad thing. We can’t live our lives with unchecked impetuosity and alacrity, because we have responsibilities. We have to be wise, we have to be smart, we have to be safe. Sometimes we have people to look after, needs to be met. Far too often, we extend our caution and walls for protection to realms of our lives where they aren’t meant to be. At least not to the degree where we keep them.

Specifically, I’m talking about our relationships: with our partners, friends, family members, neighbors; with God and the mystery of the Divine; and with ourselves.

This is what we do: we erect walls of safety and stability for a very obvious and logical reason we don’t want to get hurt.  Because there’s a very possible and maybe even likely risk that being vulnerable and present and holding on with all of our emotional and spiritual might to someone else, to God, or to our own feelings and our own emotions can bring with it very real and very intense pain.

But Yaakov’s story tells us it’s worth it.

More than that: it’s the point. It’s the point of all of this.

Ultimately, life isn’t about birthrights and inheritances, things and wages. It’s about wrestling. It’s about stripping away from our hearts the fortifications we’ve worked so hard for so long to build and to encounter one another, encounter God, and ourselves with honesty, openness, and love — even knowing that being vulnerable comes with the likelihood of being hurt.

And to do it anyway.

Because when we let go of all of that other stuff. When we recognize what truly matters. We recognize that what truly matters is THIS. Is Us in relationship to one another, it is nothing short of transformational. It transforms us.

It puts us right where we are supposed to be, so that we can journey together — bruised and battered, limping and hobbling — toward something good, to something holy, and valuable beyond measure.

Who is Yaakov wrestling with? It doesn’t matter.

What matters is that he wrestled in the first place. He didn’t have to. He might not even have been expected to. But he did.

And he took a beating. But he didn’t let go. He held on. And because he did, he was forever changed.

That, my friends, is our Torah.

This story is for us. That’s its purpose. That’s what it’s there for.

Let’s embrace it. Let’s look at the people and things around us that truly matter, and let’s wrestle with them — no matter how much it hurts.

And let’s not let go until each and every one of us is blessed.

Shabbat Shalom.