Twin-brother of Yaakov, and an archenemy of the People of Israel – an ancestor of Edom (Rome and Christianity), of Amalek, and of Haman – the first-born of Yitzchak and Rivkah.
The very first thing the Chumash tells us about the brothers Yaakov and Esav as they grew up is that “Esav was a skilled hunter; a man of the field, and Yaakov was a man of tranquility, whose desire it was to sit in the tents” (of Shem and Ever, who were conduits of ancient wisdom, from the time of Noach and earlier). The Chumash then informs us that Yitzchak preferred Esav, the hunter, while Rivkah greatly preferred Yaakov.
The Torah then describes a revealing transaction: Yaakov was cooking a red stew of lentils for the mourners, because Avraham Avinu had just died. Esav burst in, famished and exhausted from the field, and demanded that Yaakov give him some of the stew. Yaakov said he would do so, if Esav transferred to him all the spiritual benefits of the first-born. Esav says that at this point, the birthright means nothing to him, and the Torah concludes this portion with the expression, “…and Esav held the birthright in contempt.” (Bereshit 25:34)
One day, Rivkah hears Yitzchak say to Esav that he feels that he will die soon, and he wishes to bless him. He sends him to the field to capture and prepare game for him, and tells him that subsequent to that he will bless him. She sees in her prophetic vision that Esav’s receiving the blessing from Yitzchak would be a disaster for the world, because it would block the entry of holiness into the world. She commands Yaakov to impersonate Esav by wearing the latter’s hunter’s clothing and bring to his father game that Rivkah will prepare. The point is that then Yitzchak will bless Yaakov. When Yaakov comes to his father, Yitzchak feels his clothing, and says, “The voice is the voice of Yaakov, but the hands are the hands of Esav!”
When Esav discovers what Yaakov has done, he lets out a loud and bitter cry. Some commentators relate this cry of despair to the similar cry let out by Mordechai when he learns of the genocidal plot that Haman, a descendant of Amalek and of Esav, has in mind for the Jews at the time of the Persian Exile.
Esav declares his intention to kill Yaakov, and Yaakov is forced to flee to the home of Lavan, Rivkah’s brother. At the end of his stay at Lavan’s house, he and his household encounter Esav with a large armed force. The Torah says that the brothers kissed, but over the Hebrew word for “Kissed,” there are dots written. According to one opinion, the dots signify that although Esav will turn out over history to be a terrible enemy of the Jewish People, there is a possibility that he can be reformed. Rabbi Shimon bar Yochai says “It is a ‘Halachah L’Moshe MiSinai,’ an irreversible fact of history that Esav and his descendants hate the Jewish People, and can never be reformed. The dots signify that just at this particular time, Esav kissed Yaakov sincerely.” The jury is still out.