The scene is set: Yitzchak is old and blind, and he wants to bless his sons, Eisav and Yaakov, before he dies. The most significant blessing Yitzchak will bestow is the ancestral blessing of Avraham, delineating which one of the sons will carry on the legacy of Yitzchak’s father Avraham, be the progenitor of the Jewish people, and inherit the Land of Israel. Yitzchak tells Eisav to hunt and prepare food so Yitzchak may bless him. Yitzchak’s wife, Rivkah, overhears this and sends Yaakov, dressed in Eisav’s clothing, to fool his father into giving the vital blessing to him instead of Eisav. The guise seems to work—Yitzchak blesses Yaakov, thinking he is Eisav. When Eisav comes in and discovers that Yaakov stole his blessing, he threatens to kill Yaakov, beginning a twenty-year feud between the brothers. Rivkah tells Yaakov to run away to the land of Charan to avoid Eisav’s wrath.
Why does Rivkah want Yaakov to receive the ancestral blessing rather than Eisav? This question seems to be easy enough to answer. Firstly, Eisav is a hunter, a man of the field (BeReishit 25:27) whereas Yaakov lives in tents (ibid.), as his grandfather Avraham did (18:1). Additionally, Eisav is married to two Hittite women (26:34), a practice that greatly distressed his grandfather Avraham (24:3) as well as his parents, Yitzchak and Rivkah (26:35), but Yaakov is unmarried. The only valid reasoning as to why Eisav should be the rightful recipient of the blessing would be that Eisav is the firstborn, and even that argument does not hold water because Eisav sold his birthright to Yaakov for a pot of stew (25:33).
It is clear that the ancestral blessing should have been given to Yaakov all along.
So why does Yitzchak attempt to give the blessing to Eisav? What is he thinking?
In order to answer this question, we must analyze the text of all three blessings in Parashat Toledot: the Berachah Yaakov steals from Eisav, the Berachah Yitzchak gives Eisav when Eisav shows up later, and the Berachah Yitzchak bestows upon Yaakov before Yaakov leaves for Charan. As we shall see, there is a stark contrast between the first two Berachot and the third one.
Yitzchak’s first blessing, given to Yaakov disguised as Eisav, reads: “VeYitein Lecha HaElokim MiTal HaShamayim UMiShemanei HaAretz, VeRov Dagan VeTirosh. Ya’avducha Amim VeYishtachavu Lecha Le’umim; Hevei Gevir LeAchecha VeYishtachavu Lecha Bnei Imecha; Orerecha Arur, UMevarachecha Baruch,” “God shall give you from the dew of the heavens and the fatness of the earth and much wheat and wine. Nations shall serve you, and kingdoms shall bow to you; be a master over your brother, and the sons of your mother will bow to you; those who curse you will be cursed, and those who bless you will be blessed” (27:28-29).
The common theme across this blessing seems to be wealth and power. The beneficiary of this blessing will have ample food, will rule over nations and his brother, and will reciprocate to anyone who respects or disrespects him. This blessing is perfectly suited for a powerful hunter with leadership potential, namely Eisav, the intended recipient. However, the Berachah does not mention anything about Avraham, the Jewish people, or the land of Israel, things that ought to be in the ancestral blessing.
Yitzchak’s later blessing to Eisav follows the same vein as the first blessing that Yaakov stole: “Hinei MiShemanei HaAretz Yihyeh Moshavecha UMiTal HaShamayim MeiAl; VeAl Charbecha Tichyeh VeEt Achicha Ta’avod, VeHayah Ca’asher Tarid UPharakta Ulo MeiAl Tzavarecha,” “The fatness of the land shall be your home, as well as the dew of the heavens. You shall live by your sword and serve your brother, but when you grieve, you shall throw his yoke off your neck” (27:39-40).
Again, this blessing appeals to Eisav’s personality—it promises lots of food and a life of military power. The only true difference between this blessing and the first one is that here, the blessing states “you shall serve your brother” as opposed to “be a master over your brother.” But this change makes sense, as Yitzchak already told Yaakov that Yaakov would rule over Eisav, and Yitzchak couldn’t change his mind now.
The third blessing is quite different: “VeKeil Shakai Yevareich Otcha VeYafrecha VeYarbecha VeHayita LiK’hal Amim; VeYitein Lecha Et Birkat Avraham Lecha ULeZaracha Itach Lerishtecha Et Eretz Megurecha Asher Natan Elokim LeAvraham,” “God shall bless you, and you shall multiply and become a nation. He shall give you the blessing of Avraham, to inherit the land you live in, that He gave to Avraham” (28:3-4).
This blessing is drastically different than the previous Berachot. It does not mention food nor ruling over anybody. It only mentions the recipient becoming a nation, following in the ways of Avraham, and inheriting Israel—the three exact characteristics mentioned above as the defining traits of the ancestral blessing.
The wording of the blessings is evidence that the ancestral Berachah to carry on the legacy of Avraham was earmarked for Yaakov all along. Yitzchak never intended to give that blessing to Eisav; Yitzchak wanted to give Eisav the blessing Eisav would appreciate most—food, power, and respect. It is likely that if everything had gone according to plan, Yitzchak would have blessed Yaakov with the legacy of Avraham as soon as he was finished with Eisav. A good father loves each of his sons for what that son does best.
Why does Rivkah not understand this? Perhaps she is fixated on the prophecy she received when she was pregnant with Yaakov and Eisav: “Rav Ya’avod Tza’ir” (25:23). Rivkah interpreted this to mean “the older one [Eisav] shall serve the younger one [Yaakov],” so she does everything in her power to fulfill God’s prophecy and ensure that Yaakov receives the Berachah to rule over his brother. Yitzchak, however, knew that prophecies should not be taken at face value—if the prophecy Avraham received for Akeidat Yitzchak had been taken literally, Yitzchak would have been slaughtered. Yitzchak understood that the prophecy was not crystal-clear, as the words “Rav Ya’avod Tza’ir” can be translated as either “the eldest will serve the youngest” or “the eldest will work the youngest.” Yitzchak knew the superiority could go either way, so he blesses Eisav with military power while blessing Yaakov with the legacy of Avraham.
Knowing the true nature of Eisav’s and Yaakov’s blessings provides a deeper meaning to the story of their reconciliation in Parashat VaYishlach. Eisav approaches Yaakov with 400 men (33:1), a perfect fulfillment of his military-strength blessing. Yaakov approaches Eisav with so much family and so many animals that Eisav wonders aloud who and what they are (33:5, 33:8), a perfect fulfillment of Yaakov’s great-nation and wealth blessings, respectively.
But then Yaakov gives dozens of his animals to Eisav and refers to Eisav as “my master.” Why does he do this? Both of these things, animal wealth and mastery over the other brother, originate from the first blessing, the one Yaakov stole from Eisav. By sending Eisav animals and words of submissiveness, Yaakov returns the blessing he stole so long ago, realizing that Eisav was the rightful recipient of the blessing all along.
This theory is strengthened by the words Yaakov says to Eisav: “Kach Na Et Birchati Asher Huvat Lach,” “Take my blessing that was brought to you” (33:11). These words on a superficial level may refer to the animals Yaakov sent Eisav, but the language “Birchati” makes it clear that Yaakov’s intention is to return the Berachah that rightfully belonged to Eisav all along.
And why does Yaakov want to return the blessing? He explains himself later in the same Pasuk: “Yeish Li Chol,” “I have everything” (33:11). Yaakov tells Eisav that he does not want the first blessing anymore because he is content with the third blessing. Yaakov does not want wealth or mastery over Eisav because the legacy of Avraham, means Chol, everything, to him.
Once Eisav realizes that Yaakov is truly sorry for stealing his blessing and sincere in his offer to give it back, Eisav accepts Yaakov’s animals, accepting his apology. Yitzchak’s original plan was spot-on: Eisav is happy to have wealth and mastery over Yaakov, while Yaakov is happy to not to deal with it so he can concentrate on his true mission, the Jewish people. The brothers part ways amicably.
May we be Zocheh to realize, as Yaakov Avinu did, that God and family are all we need to live a fulfilled life.
 Rashbam to BeReishit 25:23 says that Rivkah saw that God loved Yaakov more than Eisav, so she did the same.
 See Ha’amek Davar, BeReishit 25:23