24 And when her days to be delivered were fulfilled, behold, there were twins in her womb. 25 And the first came out red, all over like an hairy garment; and they called his name Esau. 26 And after that came his brother out, and his hand took hold on Esau’s heel; and his name was called Jacob: and Isaac was threescore years old when she bare them. 27 And the boys grew: and Esau was a cunning hunter, a man of the field; and Jacob was a plain man, dwelling in tents. 28 And Isaac loved Esau, because he did eat of his venison: but Rebekah loved Jacob.
I imagine that this detail about Jacob reaching out and taking hold of Esau’s heel was preserved to us by Rebekah. Because of what God had foretold of her twins, she would have been the most likely to perceive the significance in the younger brother grabbing hold of the other’s heel, as if to catch and surpass him.
From the very moment of their birth the two were opposites to one another, and so they continued throughout the rest of their lives. Esau became hairy and wild and beloved of his father, Jacob smooth and calm and beloved of his mother.
Esau was expected to receive Isaac’s blessing and inheritance, because that was what the culture of the time said should happen. But God had already revealed to Rebekah that the custom of firstborn sons receiving the inheritance meant very little to Him. He would not be choosing Isaac’s successor based on which son happened to be born first, but on which of the sons was worthy.
God’s choice of Jacob over Esau reminds me of another firstborn that he passed over years later, when Samuel the prophet was looking for the next king of Israel. Samuel was going to anoint Eliab, Jesse’s firstborn, but the Lord told him “I have refused him: for the LORD seeth not as man seeth; for man looketh on the outward appearance, but the LORD looketh on the heart” (1 Samuel 16:7). Then and now, what matters to God are not the random circumstances of our birth, but the intentional choices of our life.