בראשית, פרק כ״ח, פסוק ט׳

After losing the family blessings and realizing his Canaanite wives deeply upset his parents, Esau sets out on a journey of apparent correction. He turns to his extended family to find a more suitable match, hoping to please his father and perhaps reclaim Abraham's inheritance [חזקוני, בכור שור]. However, his motives are complex and far from sincere. Some suggest Esau actually planned to join forces with Ishmael to kill Isaac and Jacob [הדר זקנים], or that he wanted to free his future descendants from serving Jacob by tying his lineage to Ishmael's family [פרדס יוסף]. The primary approach among commentators views this union simply as a natural pull between wicked individuals. Just as a bad palm tree naturally grows near barren trees, Esau was drawn to his own kind [תורה תמימה, חזקוני].

Esau marries a woman named Mahalath. Although she is known by another name elsewhere, she is called Mahalath here to hint at the concept of forgiveness. Since a bride and groom have their past wrongs forgiven on their wedding day, Esau tried to use this occasion to present a false show of repentance to his father [תורה תמימה, מחוקקי יהודה, ביאור יש״ר, חומש קה״ת].

The new bride is identified as the sister of Nebaioth. One explanation for mentioning her brother is that Nebaioth was the eldest and most respected sibling, making it honorable to associate her with him [רשב״ם, רד״ק, אבן עזרא, חזקוני]. Another view suggests that since Ishmael had several wives, noting Nebaioth clarifies that they were full siblings from the same mother [ביאור יש״ר, תולדות יצחק]. A widely accepted historical approach explains that Ishmael originally arranged the marriage but died between the engagement and the wedding. Consequently, Nebaioth stepped in to give his sister away [רש״י, העמק דבר, גור אריה]. By calculating Ishmael's age at the time of his death, commentators deduce that Jacob was sixty-three years old during these events. This timeline reveals that on his way to Haran, Jacob spent fourteen years hiding and studying Torah in the study hall of Eber [רש״י, שפתי חכמים].

Despite his effort to present this as a proper marriage, Esau ultimately fails. Rather than sending away his troublesome Canaanite wives, he simply adds this new wife to his household. This choice highlights his hypocrisy, as he merely adds more wickedness to his existing bad situation [רש״י, ביאור יש״ר, חומש קה״ת]. Some explain that Esau placed his new wife in a position of authority over the others [העמק דבר, רד״ק]. Others add a deeper insight into this union: while a first marriage might not fully reflect a person's character, later marriages are matched exactly to a person's deeds. Therefore, the woman Esau added to his home was just as wicked as he was, making them a perfectly suited pair [נחל קדומים, פרדס יוסף].