A pivotal transition occurs as the physical military campaign of the Israelites gives way to a period of spiritual preparation led by Moses before they enter their new land. The primary approach among commentators is that Moses deliberately delayed his words of correction until after the nation had defeated the Amorite kings. This delay was driven by a deep understanding of human psychology. Had Moses offered a harsh critique before securing any land for the people, they might have rejected his words. They could have easily accused him of looking for excuses to cover up an inability to bring them into the land, challenging him by asking what good he had actually done for them. Instead, by first providing a tangible benefit—a decisive victory over two mighty kings and the inheritance of their territory—Moses fostered a sense of gratitude and humility. Only then was the nation truly ready to listen and internalize his message [רש״י, בכור שור, שפתי כהן, חומש קה״ת].
Beyond creating emotional readiness, the military success provided the Israelites with a period of physical rest and calm. This peace was essential, freeing their minds to focus, listen, and engage deeply in the study of Torah [ספורנו, העמק דבר]. Furthermore, defeating such formidable enemies filled the people with confidence and hope as they faced the impending conquest of Canaan [ביאור שטיינזלץ].
The specific details of these conquered kings highlight the sheer magnitude of the miracle. Sihon was an exceptionally harsh and aggressive ruler, and his capital, Heshbon, was a heavily fortified city. This presented a double challenge for the Israelites, making their triumph all the more remarkable [רש״י, גור אריה]. Interestingly, Heshbon was not originally Sihon's city; he had previously captured it from the king of Moab and established it as his own capital [רמב״ן, הטור הארוך].
The geographic description of the second king, Og, introduces two distinct locations. Commentators differ on the exact nature of the first location, Ashtaroth. One approach suggests the name implies strength and rocky cliffs, indicating that Og lived in a fortified stronghold atop a steep, inaccessible mountain [רש״י, מזרחי, פני דוד]. Another perspective links the name to wealth, referring to the massive flocks of sheep that grazed on those high mountains, bringing great riches to their owners. This view also notes that the local idolatry was fashioned in the shape of sheep [רמב״ן, רבנו בחיי, ריב״א]. Historically, this area is identified as the ancient city of the giant Rephaim, making Og the very last survivor of that formidable race [רמב״ן, ביאור יש״ר].
While two names are mentioned, the primary approach among commentators is that they were not separate capital cities. Rather, Ashtaroth was the name of the steep, heavily fortified mountainous region, while Edrei was the actual royal city situated in the plains below. The king's palace was located in Edrei, and it was there that Og gathered his entire army to wage war against the Israelites [רמב״ן, רבנו בחיי, הכתב והקבלה, פני דוד]. Ultimately, Og's reign in these mighty locations is described as a thing of the past, emphasizing that he ruled there securely only until he was struck down in battle and completely lost his kingdom [הכתב והקבלה].