The return of the messengers to Jacob carries immense dramatic weight, bringing an ambiguous and threatening message that forces him to decode his brother's true intentions after years of estrangement. Interestingly, the messengers report no actual dialogue with Esau. Driven by arrogance, Esau completely ignored them, refusing to answer directly. Consequently, the messengers had to piece together his intentions purely from what they observed on the ground [העמק דבר, בכור שור, ביאור שטיינזלץ].
The report they deliver is layered with disappointment. The primary approach among commentators is that Jacob hoped to find a loving brother, but instead discovered that the wicked Esau still clung tightly to his old hatred [רש"י, רד"ק, הכתב והקבלה, מזרחי]. Some explain that Esau displayed a welcoming, brotherly exterior while harboring deep resentment within, leaving the messengers thoroughly confused by the contradiction [אור החיים, כלי יקר]. Furthermore, Esau seemingly rejected Jacob's submissive overtures. By refusing to accept Jacob treating him as a superior, Esau signaled that Jacob's blessings of leadership had never truly materialized, and the two remained absolute equals [כלי יקר, מלבי"ם]. On their part, the messengers tactfully avoided referring to Esau as a superior in Jacob's presence, recognizing that it is highly disrespectful for a servant to elevate another person while standing before their own master [העמק דבר, שד"ל].
The news that Esau is actively marching toward Jacob carries multiple implications. On a basic level, it is a simple parallel: just as Jacob journeys toward Esau, Esau journeys toward Jacob, and their meeting is imminent [רמב"ן, הטור הארוך]. However, other commentators view this advance as a severe escalation. Esau was not appeased by the gifts sent ahead; rather, he is aggressively setting out to confront Jacob and block his entry into the land [ספורנו, הכתב והקבלה, מלבי"ם, פנים דוד]. On a spiritual plane, this approaching force is not merely human. Esau is accompanied by his guardian angel, a spiritual entity marching out to wage war against Jacob [רבנו בחיי].
The most alarming detail of the report is the presence of four hundred men accompanying Esau, a fact that sparks a sharp debate. A minority view suggests this is actually a positive development. In this reading, Esau was overjoyed to hear of Jacob's return and gathered a massive entourage to honor him out of deep brotherly love [רשב"ם, חזקוני]. The messengers themselves might have genuinely believed Esau was approaching in peace [שד"ל, ביאור יש"ר]. However, the primary approach firmly rejects this optimistic interpretation. If Esau's intentions were peaceful, Jacob would not have been struck by the profound terror that soon drives him to plead with God for his life [אם למקרא]. Instead, an army of four hundred men is an undeniable declaration of war [ספורנו, רד"ק, כלי יקר]. Esau's reliance on such a massive force highlights his dependence on physical might and military power [רבנו בחיי]. At the very least, this overwhelming army was designed to strike fear into Jacob's heart and force his surrender without a single blow [קונטרס חיבה יתירה]. In a mystical sense, these hundreds of men embody divine forces of strict judgment aligning against Jacob [שפתי כהן, רקנאטי]. Ultimately, while the messengers may have failed to grasp the full severity of the situation, the wise Jacob read the circumstances perfectly, understanding without a doubt that his brother was coming for war [ביאור יש"ר, קרני אור].