The Israelite delegation stands before Sihon, king of the Amorites, presenting a diplomatic proposal to pass through his territory. This appeal reflects a desire to advance toward the land of Canaan with minimal friction, accompanied by a commitment to maintain order and respect local property. However, beneath the surface of this request lie complex messages of strength and strategic calculation. When comparing this message to the earlier appeal made to the king of Edom, striking differences emerge. With Edom, the request was framed as a plea. Here, Moses avoids any language of pleading, as he does not intend to overly appease Sihon. Instead, he delivers a formal notification and an opening for peace [הטור הארוך, העמק דבר]. Furthermore, the Israelites present themselves differently. To Edom, they spoke as a multitude of scattered individuals, intentionally downplaying any military threat since they were forbidden to fight them. Against Sihon, they speak as a single, unified entity, presenting themselves as a cohesive and formidable army marching together [הכתב והקבלה].
The specific terms of the passage guarantee that the Israelites will not deviate from the main route or drink from any privately owned wells. They commit to traveling strictly along the public highway designated for the masses, or whichever specific path the king dictates [ביאור שטיינזלץ], continuing only until they successfully cross the territorial border [ביאור יש״ר]. Some commentators emphasize that the Israelites never intended to march directly through the populated cities. Rather, they asked only to skirt the outer borders of the territory, just as they had proposed to Edom and Moab [דעת זקנים, בכור שור].
This diplomatic outreach raises a significant question. The Amorites were one of the seven Canaanite nations that the Israelites were explicitly commanded to destroy entirely. How, then, could Moses offer Sihon peace and a safe passage agreement? One perspective explains that Moses had no initial intention of conquering the territory east of the Jordan River. His sole objective was to cross over and conquer the western land of Israel so that the entire nation could settle together. Had the tribes of Gad and Reuben not requested this eastern territory later on, it would have been left completely unsettled [הטור הארוך, גור אריה, העמק דבר].
A legal approach suggests that the commandment to annihilate the seven nations only applied once actual warfare commenced. Prior to the outbreak of war, it was permissible, and even proper, to offer terms of peace. If the Amorites had accepted the peace offer, agreed to pay taxes, submitted to Israelite rule, and abandoned their idolatry, there would have been no prohibition against leaving them alive [שפתי חכמים, מזרחי, דברי דוד]. Other explanations propose a geographic distinction, arguing that the command of total destruction only applied to Amorites living within the western borders of Israel, not those residing east of the Jordan [דברי דוד, הדר זקנים]. Alternatively, the diplomatic approach was necessitated by the region's complex history. The land of Heshbon originally belonged to Moab, a nation the Israelites were strictly forbidden to attack. Since Sihon had captured this territory from Moab, the Israelites felt compelled to formally request permission to pass through it [שפתי כהן].
Although Sihon ignored the peaceful overture and immediately mobilized for war, the primary approach among commentators is that Moses chose to initiate peace even though he was not explicitly commanded to do so. He derived this leadership principle from the ways of God Himself, who offered the Torah to the other nations of the world before giving it to Israel, even though God knew they would reject it. Following this divine example, Moses chose to extend an offer of peace before resorting to the sword [רש״י, ריב״א].