Genesis 25:26

ואחרי כן יצא אחיו וגו AND AFTERWARDS HIS BROTHER CAME OUT, ETC. — I have heard a homiletical midrash that expounds it according to its simple meaning: It was with justice that he was grabbing him to hold him back. Jacob was conceived from the first drop and Esau from the second. Go and learn from a tube with a narrow opening - put in it two stones, one after the other. The one that goes in first will come out last, and the one that goes in last will come out first. It comes out that Esau, who was conceived last, came out first, and Jacob, who was conceived first, came out last. And [so] Jacob came to hold him back, so that the first for birth would be the same as the first for conception; and he would open [his mother's] womb and take the first-born status with justice (see Genesis Rabbah 63:8).

Afterward came forth his brother, and his hand had hold on the heel of Esau. And they called his name Jakob (Yaakov). And Izhak was a son of sixty years when he beget them.

ויקרא שמו יעקב. The word means he will remain at the heel, and the tail-end. This is based on the future mode of the word יעקב. Our sages (quoted by Rashi) say that the subject in our verse is G’d Who named Esau’s brother Yaakov, the reason for the unusual formulation being that after the destruction of the Kingdom of Edom and other nations, successor of Esau, only Yaakov and his descendants will remain. Our sages base all this on Jeremiah 46,28 אעשה כלה בכל הגויים...ואותך לא אעשה כלה, “I will make an end of all nations…but I will not make an end of you.”

ואחרי כן...וידו אוחזת בעקב עשו, this too, was an allusion that at the end of time he would dominate Esau, as a human being dominates something matters which he grabs with his hand. The heel is the lower end of the body. It was clearly a hint from G’d concerning the future, as a normal baby does not manage to extend his hand outside the placenta and make contact with its twin.

ויקרא שמו יעקב, Yitzchok named him thus.

ויצחק בן ששים שנה, this is mentioned to let us know that Rivkah had been unable to bear a child during 20 years.

ויקרא שמו יעקב, “he called his name Yaakov.” The name Yaakov has four letters, symbolising the four crowns with which his descendants would “crown” the Almighty. The letter י symbolises the Ten Commandments. The letter ע symbolises the seventy elders. The letter ק symbolises the length of hundred cubits of the Sanctuary built by King Solomon. (Kings I chapter 7) The letter ב symbolises the two Tablets upon which the Ten Commandments were inscribed. The Israelites were redeemed from slavery in Egypt due to the merit of Yaakov. We know this from Psalms 105,10: ויעמידה ליעקב לחק, לישראל ברית עולם, “He confirmed it as a decree for Yaakov, as an eternal covenant for Israel.” If it had not been for the fact that G–d wanted Yaakov to be born, He would not have saved Avraham from Nimrod’s furnace. (B’reshit Rabbah 63,2).This is what the prophet Isaiah 29,22, had in mind when he wrote: כה אמר ה' אל בית יעקב אשר פדה את אברהם, “thus said the Lord to the house of Yaakov which had redeemed Avraham. A different interpretation of that verse in Isaiah [which begs the question, Ed.] by Yalkut Shimoni: Yaakov released Avraham from the heartache associated with trying to raise children. [He did so by successfully raising all his children in his spirit, something neither Avraham nor Yitzchok had been able to do. Ed.]