Jacob orchestrates a calculated diplomatic and psychological strategy ahead of a fateful encounter with his brother. By dividing a massive tribute into separate flocks, he provides his shepherds with precise instructions on how to address Esau, aiming to soften his anger and demonstrate deep respect and submission.
The central message the shepherds are required to convey is that they are Jacob's servants, that the entire procession of flocks is a gift presented to his master Esau, and that Jacob himself is walking right behind them [ספורנו, ביאור שטיינזלץ]. Jacob commands every shepherd to deliver this identical message so that Esau will recognize their consistency, proving that Jacob's intentions are genuinely peaceful [ביאור יש״ר]. However, they are instructed to convey the spirit and main point of the message rather than repeating the exact same words verbatim. This ensures their declarations do not sound like a rehearsed, staged testimony [חתם סופר].
The primary approach among commentators is that Jacob instructs the later groups to initiate the conversation the moment they see Esau, even if he stops asking questions after encountering the first groups. This serves a dual purpose. First, it ensures that the phrases expressing submission and respect echo repeatedly in Esau's ears, creating a profound psychological impact [העמק דבר]. Second, it creates the impression that they are approaching him out of brotherly love and a genuine desire to meet, rather than out of fear [מלבי״ם]. Conversely, another perspective suggests that the shepherds are only meant to answer if Esau actively approaches them and asks about their business [שד״ל].
The instructions are given to the second, third, and all subsequent groups, prompting a discussion about the total number of flocks. One approach maintains there are five flocks in total, corresponding to the five species of animals sent, leaving two flocks after the initial three [אבן עזרא, יהל אור]. Another view argues there are ten flocks, as the males and females of each species are separated [קרני אור]. Since the inclusive language used for the remaining groups typically refers to three or more items, a question arises regarding how it applies if only two flocks remain. Commentators explain that the command is not directed solely at the head shepherd of each flock, but rather to the numerous servants walking with and tending to the animals. Therefore, the phrasing accurately encompasses everyone present [העמק דבר, פרדס יוסף].
An unusual phrasing regarding the moment the servants encounter Esau seems somewhat redundant, as it is obvious they will only speak to him upon meeting him. This perceived redundancy leads to a completely different interpretation of Jacob's warning. Instead of referring to the moment they find Esau, the phrasing is understood as an instruction for the servants to verbally exclude themselves from the tribute. Jacob strictly warns his servants to be precise with their words so that Esau understands only the animals are the gift, while the human servants leading them are absolutely not part of the property being handed over [הכתב והקבלה].