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Messianic Rabbi: The Blessing of Esau Brings Freedom

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Rabbi Eric Tokajer

Read Time: 4 Minutes 55 Seconds

Growing up in synagogue, I was taught about the heroes of the Bible: Abraham, Isaac, Jacob, Moses, Joshua, David, Solomon and Samson. When I became a believer in Yeshua, the writings of the New Testament new heroes were added to the list, including Peter, Paul, Jacob (James) and John.

Along with the heroes of the Bible, I was also taught about the biblical villains: Pharaoh, Haman, the Philistines, and of course, Esau.

In Shabbat school, I was taught about Esau, that first he so despised his covenant birthright that he sold it to Jacob for a bowl of red lentil soup. Our teacher shared from Malachi 1:1-3:


“I loved you, says Adonai. But you say: ‘How have you loved us?’ Was Esau not Jacob’s brother?—it is the declaration of Adonai—Yet I loved Jacob and Esau I hated. I made his hills a wasteland and gave his inheritance to jackals of the wilderness,” (Mal. 1:1-3).

This verse planted the seed in my mind that Esau was to be thought of as hated and evil. Later, when I accepted that the New Testament was Scripture also, I read Romans 9:13 and Hebrews 12:16, which both seemed to confirm the status of Esau as a biblical villain.

“As it is written, ‘Jacob I loved, but Esau I hated,’” (Rom. 9:13).

“Also see to it that there is no immoral or godless person—like Esau, who sold his birthright for one meal. For you know that later, when he wanted to inherit the blessing, he was rejected. He found no chance for repentance, though he begged for it with tears,” (Heb. 12:16-17).


This verse is referring to Genesis 27:38:

“Esau said to his father, ‘Do you just have one blessing, my father? Bless me too, my father!’ And Esau lifted up his voice and wept.”

However, when I was reading in the book of Genesis, I came across a verse that changed my perspective about Esau and I hope it will change yours also. This verse not only changed my understanding of the story of Esau, but it helped to increase my understanding of G-D’s grace and mercy. The verse is in Genesis 27 and is the last sentence of the blessing that Isaac speaks over Esau.

Here is the verse:


“By your sword shall you live, and your brother shall you serve. But when you tear yourself loose, you will tear his yoke off your neck,” (Gen. 27:40).

Notice these powerful words spoken by Isaac over his son Esau. I am sure you are familiar, at least in concept, with the words in the first sentence. But, the second sentence is often missed or skipped over. Yet, it is this last sentence of the blessing that holds within it a deep promise that we can hold onto even today. When Isaac spoke these words to Esau, he didn’t say “if” you tear yourself loose; Isaac said “when” you tear yourself loose. These words hold within them the promise of deliverance and restoration for Esau.

Yes, Esau thought so little of his birthright that he sold it for a bowl of soup, and yes, he wanted to kill his brother, and yes, he married a Canaanite woman in rebellion against his parents desires. All of the above is true. It is also true that Esau sought repentance and none was found. However, it is also true that the blessing spoken by Isaac over Esau came to pass and Esau tore himself loose from the yoke. We see this demonstrated when Jacob returns home from the house of Laban and Esau meets him on his way home as we read in Genesis 33:4:

“But Esau ran to meet him, hugged him, fell on his neck and kissed him—and they wept.”


Notice as you read these words in context that as Jacob is returning home, he is still living in fear of Esau. However, Esau is not walking in anger and hatred; Esau is walking in love and forgiveness.

Esau, it turns out, is not the villain we make him out to be. Esau was a man who, like all of us, chose to love the things of the world over the things of G-D. When he realized the cost of what his choice cost him, Esau sought repentance (turning around or change) with tears. However, the repentance Esau sought was a change in his situation and not a change in Esau. We see this in how Esau responds both in his anger against his brother, demonstrated by his desire to kill Jacob, and his anger at his parents, demonstrated by his decision to marry a Canaanite woman.

However, we also see Isaac’s blessing come to pass in the life of Esau when we read of his forgiveness of Jacob and the restoration of his love for his brother as he runs to hug and kiss Jacob.

In these actions, we see the fruit of repentance in the actions of Esau. As I read the promise in Genesis 27:40 and saw the fulfillment of the promise in Genesis 33:4, these words not only changed my understanding of the story of Esau, but they increased my understanding of G-D’s grace.


Not only was I able to look at Esau differently, but I was able to extend the grace of G-D demonstrated in Esau’s life into my life. Like Esau, there have been times when I’ve chosen the ways of the world over the ways of G-D. The result of my choices were the same as the result of Esau’s choices. My actions caused me to miss out on the blessing of my Heavenly Father. Like Esau, sometimes I’ve responded in tears, asking for G-D to change my circumstances instead of asking G-D to change me. Like Esau, sometimes this caused me to react in anger and make more choices contrary to G-D’s ways.

Yet, like Esau, when the time came that I wanted to free myself from the yoke my actions placed upon my life, through real repentance, I was able to tear that yoke off of my shoulders and be set free.

The truth is that, in a real way, we are all Esau’s, and like Esau, our Father has given us the promise of deliverance from the bondage of our sinful choices. The only question is: will we desire to tear ourselves loose, so that we can tear the yoke off of our necks?

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Eric Tokajer is the author of “Overcoming Fearlessness,” “What If Everything You Were Taught About the Ten Commandments Was Wrong?,” “With Me in Paradise,” “Transient Singularity,” “OY! How Did I Get Here?: Thirty-One Things I Wish Someone Had Told Me Before Entering Ministry,” “#ManWisdom: With Eric Tokajer,” “Jesus Is to Christianity as Pasta Is to Italians” and “Galatians in Context.”

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