Yitzchak was not entirely oblivious to Eisav’s unrefined character and conduct (see Bereshit 26:35; Rashi on Bereshit 27:21), yet he intended to bestow upon him the most powerful blessings. Surely, his desire to bless Eisav was not based only on what he did not know about him, but also on what he did see in him.
The Torah relates that Yitzchak devoted a great deal of energy to digging water wells, restoring old wells and searching for and developing new sources of fresh water.
Chassidus explains that this hobby was not a meaningless detail in Yitzchak’s life, but a reflection of his distinctive nature, and his unique path in the service of G-d. Where others saw dirt and gravel, Yitzchak dug deeply to reveal springs of life-giving water that ran beneath the earth. This means, in spiritual terms, that Yitzchak devoted himself to refining the unrefined, unearthing and cultivating the potential within all creation to recognize its G-dly source.
Seeing the Potential
Accordingly, we can understand why Yitzchak desired to bless Eisav. Despite Eisav’s disreputable behavior, Yitzchak had the ability to see the great spiritual potential associated with Eisav’s soul. Yitzchak therefore hoped that his powerful blessings would successfully excavate the spiritual treasures that lay hidden in his child.
Nevertheless, despite Eisav’s immense potential, his actual lowly state was such that in reality the blessings would not have had the desired effect on him. Rivka therefore deemed it necessary for Yaakov to receive the blessings instead of him.
Today, there are no Eisavs, but like Yitzchak, who labored to reveal the connection to G-d buried even within the wicked Eisav, we too must endeavor to draw near even those who seem distant from the life-giving waters of the Torah. With toil and effort, we can reveal within them their innate connection to the Source of Life. (Likutei Sichot, Vol. 15)
Adapted from the teachings of the Rebbe, reprinted from Ohr HaChassidus
And these are the generations of Yitzchak...and the first came out...and they called his name Esav (Gen. 25:19;25)
Esav is symbolic of the forces of evil and impurity, which were created for the purpose of the Jew transforming them into goodness and light. (It is due to this inner, positive reason that the Torah refers to Esav as "the generations of Yitzchak.")
The name Yitzchak is related to the word for laughter. When "Esav" is changed into good, G-d "laughs," as it were, and derives great pleasure. (the Rebbe)
That my soul may bless you (Gen. 27:4)
Why did Isaac want to bless Esau instead of Jacob? Jacob was "a pure man, a dweller in tents (of Torah)," and even without a blessing he would stay away from evil. Esau, however, was very likely to fall into bad ways, and needed the assistance of his father's blessing. (Ohr HaTorah)
And one people shall be stronger than the other (Gen. 25:23)
Rashi comments: When one rises, the other falls.
Jacob and Esau symbolize the struggle between the G-dly soul and the animal soul, between a person's good and evil inclinations. When a Jew's G-dly soul is dominant and exerts itself, there is no need to combat the animal soul—it "falls" by itself. Light does not have to fight darkness to illuminate—as soon as it appears, the darkness vanishes. So too, does the light of holiness dispel all evil. (Sefer Hamaamarim)
Esau and Jacob
The name Esau is derived from the Hebrew word meaning done or completed. Esau felt whole, satisfied and comfortable with his spiritual status, and was thus lacking any desire to elevate himself. Jacob, by contrast, is derived from the word meaning heel. No matter how high a spiritual level Jacob achieved he considered it as nothing, and was consistently motivated to elevate himself further. (Shem MiShmuel)
From our Sages reprinted from LchaimWeekly.org - LYO / NYC