The region in and around Canaan has long served as a crossroads, hosting a succession of different nations over time. In the area east of the Jordan River, ancient peoples such as the Horites originally settled the land, much like the early generations of the Rephaim, until they were eventually replaced by the descendants of Esau [ביאור שטיינזלץ].
The process by which God gave the territory to Esau's descendants was not an immediate event. Initially, they arrived as strangers, living as temporary residents among the local population in the land of Seir. It was only after a period of time that they drove out the original inhabitants and claimed the area as their own [ספורנו].
This conquest, however, did not unfold in the exact same way for all of Esau's families. This explains a dual sequence of events regarding whether the newcomers settled first and destroyed the locals later, or fought first and settled later. One group, the descendants of Esau's wife Oholibamah, had a distinct advantage. Because she was of Horite descent, her family used their local ties to settle peacefully in Seir early on. Only at a later stage did they rise up against their hosts. On the other hand, the rest of Esau's descendants, born to his Hittite and Ishmaelite wives, lacked these family connections. They could not simply move in and settle. Instead, they had to fight and destroy the Horites first before they could inherit the land and take their place. Because of its varied nature, the complex case of Esau's families serves as a model for how Ammon and Moab inherited their own lands [העמק דבר].