בראשית, פרק ל״ו, פסוק ו׳

The departure of Esau from the land of Canaan marks a definitive historical and geographical turning point. The paths of the two brothers finally separate, resolving the long-standing question of their inheritance. A chronological question arises regarding this absolute migration, as earlier events indicate Esau was already living in Mount Seir long before Jacob returned to the land. To resolve this, commentators explain that until this point, Esau's presence in Seir was only temporary. He spent time there as a military leader or wandering shepherd, while his wives, children, and the bulk of his property remained in Canaan near his father, Isaac. Only now, following Jacob's return and Isaac's passing, did Esau permanently uproot his entire family to conquer Seir and settle there [רמב״ן, שד״ל, הטור הארוך, חזקוני, ביאור יש״ר, ברכת אשר, העמק דבר].

When organizing his household for the journey, Esau gathered his wives before his children. Unlike Jacob or Moses, who prioritized placing their children first out of a need to protect them, Esau feared nothing and simply relied on his wives to care for the young [הטור הארוך]. Alongside his family, he took all his domesticated livestock [רד״ק, העמק דבר]. As he set out, his exact destination is initially left unstated. Some commentators suggest Esau simply went looking for any available territory that could offer adequate living space for his massive herds [רש״י, רלב״ג, שפתי חכמים, מזרחי, אונקלוס, נתינה לגר, שטיינזלץ]. The primary approach among commentators, however, is that he was clearly heading to the land of Seir, and the specific location is omitted simply because it is already understood from the surrounding context [רמב״ן, הטור הארוך, רבנו בחיי, בכור שור, פענח רזא, חזקוני, ביאור יש״ר]. Conversely, another perspective argues that the destination is left vague to emphasize that Esau's main goal was not to reach a specific place, but merely to distance himself from Jacob [רש״ר הירש].

The reasons for this separation operate on several levels. Practically and economically, the accumulated wealth and livestock of both brothers were so vast that Canaan could not provide sufficient pasture for them to remain together [רד״ק, מזרחי, ביאור יש״ר, רש״ר הירש]. On a legal and prophetic level, Esau had come to terms with the fact that Jacob had purchased the birthright and secured Isaac's blessing. He therefore recognized that Canaan was Jacob's exclusive inheritance, while his own destiny lay in Mount Seir [רשב״ם, רד״ק, העמק דבר, הטור הארוך, חזקוני]. It is even possible that the brothers reached a formal division agreement, where Esau took all the movable wealth left by Isaac, leaving Jacob with the ownership of the land itself [ביאור יש״ר].

Beyond physical wealth, the separation stemmed from profound personal differences. Esau felt uncomfortable with the spiritual and moral atmosphere that Jacob cultivated, prompting him to seek an environment where he could live more freely [רש״ר הירש]. Furthermore, Esau was well aware that whoever inherited the Promised Land would also have to pay the divine debt established with God in the Covenant of the Parts, which required enduring exile, suffering, and foreign enslavement. Unwilling to bear this heavy burden, and perhaps feeling a lingering sense of shame over selling the birthright, Esau chose to forfeit the Promised Land and leave of his own free will [גור אריה, חומש קה״ת].