בראשית, פרק כ״ו, פסוק ל״ד

A dramatic turning point in the history of the patriarchs unfolds through Esau's marriage, an event that exposes a profound gap between outward appearance and inner reality. This moment serves as the essential backdrop for the impending transfer of the family blessings. At this time, Esau reaches the age of forty, while his father Isaac is one hundred [רשב״ם, ביאור יש״ר]. Reaching forty was considered the proper time for marriage, representing a quarter of the human lifespan in that era and symbolizing maturity, completeness, and the natural cycles of life [גור אריה]. The primary approach among commentators is that Esau deliberately waited until this specific age to imitate his father, who also married at forty, thereby projecting a facade of righteousness and adherence to his family's traditions [רד״ק, ביאור שטיינזלץ]. Commentators compare Esau to a pig, which stretches out its cloven hooves when resting to display an outward sign of purity, deliberately masking its internal corruption. After years of violent behavior and taking women from their husbands—a description some view as an exaggeration meant to illustrate his general wickedness [ברכת אשר]—Esau now sought to present himself as a proper and upstanding man [רש״י, רבנו בחיי, צאינה וראינה].

In stark contrast to Isaac and Jacob, Esau made no effort to avoid marrying into the local Canaanite population. He chose his wives based purely on his own desires, without consulting his parents, selecting women from prominent and well-known local families [רד״ק]. He likely became acquainted with them during his family's visits to the Cave of Machpelah, which had been purchased from the Hittites [קונטרס חיבה יתירה]. Bringing Hittite women into Abraham's household completely shattered the family's spiritual destiny. While Isaac dedicated himself to building altars to God, his firstborn son introduced idolatry directly into the home, forging a bond with a nation destined for destruction [רבנו בחיי, רש״ר הירש].

Isaac's response to these marriages is a matter of debate. One perspective suggests that Isaac was negligent by failing to prevent Esau from marrying Hittite women and by not actively seeking out proper wives for him, a departure from Abraham's strict standards [ספורנו]. Conversely, another approach maintains that Isaac was fully aware that Esau was unsuited to carry the spiritual destiny of the chosen nation, and that Abraham's ultimate blessing was reserved exclusively for Jacob. Under this view, Isaac intentionally refrained from warning Esau, planning to grant him only the material blessings of this world while still loving him for his practical intellect [העמק דבר, מלבי״ם]. Ultimately, Esau's actions caused immense grief and contributed to Isaac's physical and spiritual blindness, as raising an improper son is said to dim a parent's eyes [צרור המור]. This tragic outcome eventually led to the explicit command warning Jacob never to marry a Canaanite woman [שד״ל].

The identities of Esau's wives further highlight his deceptive nature. The name Judith is a proper personal name rather than a title denoting a Jewish religious affiliation [אבן עזרא, ביאור יש״ר, מחוקקי יהודה]. However, Esau deliberately used this name to mislead his father, creating the false impression of a righteous woman who rejected idolatry [צאינה וראינה, ברכת אשר]. Judith is notably absent from the later genealogical records of Esau's descendants because she did not bear him any sons [אבן עזרא, ביאור יש״ר]. His other wife, Basemath, was also known as Adah, as it was common practice during that era for individuals to have two names [אבן עזרא, מחוקקי יהודה]. Additionally, there is a tradition suggesting that Esau did not marry Basemath at the age of forty, but rather took her as a wife at a later time [ביאור יש״ר].