וַיִּשְׁלַח יַעֲקֹב מַלְאָכִים לְפָנָיו אֶל־עֵשָׂו אָחִיו אַרְצָה שֵׂעִיר שְׂדֵה אֱדוֹם׃

 (בראשית לב:ד)

“And Yaakov sent messengers before him to Eisav, his brother … ” (Bereishis 32:4).

On this pasuk, the midrash comments, “Messengers: human messengers. Rabbanan say that they were heavenly messengers, malachim—angels.”

Zera Shimshon asks: Why did Yaakov choose to send malachim (angels) to Eisav, rather than sending regular human messengers? Why weren’t regular mortal messengers sufficient? Why did Yaakov have to send malachim?

One plausible explanation is that Yaakov intended to uncover Eisav’s genuine sentiments—a task seemingly more suited for a malach than a human. Humans can only guess what another person’s thoughts are while a malach can go into a person’s mind and see what a person is really thinking.

Zera Shimshon dismisses this explanation. He argues that malachim do not need to be physically present to understand a person’s emotions, as demonstrated in the episode where malachim informed Yosef of his brothers’ sentiments before he actually encountered them.

Zera Shimshon, therefore, refers to a midrash to explain why Yaakov sent heavenly malachim (angels) instead of human messengers to Eisav. The midrash says that this decision stemmed from Yaakov’s hope that Eisav would repent and engage in teshuvah for his previous misdeeds. Malachim—in this context—are seen as more effective in convincing and leading others towards a positive transformation. Reb Tzaddok HaCohen explains the reason for this is that the very words of a tzaddik—like Yaakov—have in them the power to impact the listener. A malach has the ability to convey the actual potent and powerful words of tzaddik, which could have a major effect on Eisav—encouraging his teshuvah. In contrast, a human messenger can only relay the intent or meaning of Yaakov’s words, not the words themselves. Consequently, Yaakov chose malachim to deliver his message to Eisav, trusting in their superior ability to transmit his words themselves and their inherent power.

Zera Shimshon delves deeper, questioning: Why was Yaakov even invested in turning Eisav into a baal teshuva? What was the rationale behind Yaakov’s concern for someone who had intentions to kill him?

Zera Shimshon explains it is written in the Gemara (Avodah Zarah 17a) that whoever is heavily involved in Avodah Zara or has a high position of authority and abuses it, it is very difficult for them to do teshuva. The difficulty of overpowering and defeating their yetzer hara causes them to “never find the path of life” meaning they will die soon after.

This struggle represents a profound and ongoing internal conflict, marked by a continuous battle against their negative impulses and desires. Interestingly, it’s not their failure in this struggle that leads to an early demise, but rather, the sheer intensity and magnitude of the battle itself. Even when they succeed in mastering these darker inclinations and embark on the path of teshuva, the extreme exertion required in this process can take a significant toll on their physical vitality. Consequently, their earnest and strenuous efforts to align with a righteous path, despite being victorious, often result in them not being able to “find the path of life.”

Chazal—in Bereishis Rabbah 63:13—notes Eisav’s engagement in Avodah Zara and, in a different midrash, it is written that he went into Mitzrayim to secure tax collection rights—a step in securing funding to harm Yaakov. This dual involvement—in idol worship and the exploitation of a public position—places Eisav squarely in the realm of those facing immense struggles with their yetzer hara. Yaakov—aware of this, and constantly under the threat of Eisav’s potential aggression—hoped that Eisav would engage in teshuvah for these specific transgressions. Yaakov understood that Eisav’s repentance—particularly for these grave actions—would likely lead to his early demise, thus removing him as a threat to Yaakov.

However, Zera Shimshon, drawing from a nuanced reading of Rashi (Bereishis 32:8), suggests that Yaakov’s intentions were not only for his personal safety but were more complex. It wasn’t merely about Eisav’s death; Yaakov desired Eisav to pass away through his teshuva. Recognizing that Eisav—as a son of Yitzchak—possessed inherent kedusha (holiness), Yaakov hoped for this latent sanctity not to be wasted. Yaakov’s strategy was not just about eliminating a threat; it was about seeking a transformative end for Eisav—a death that would come through repentance, thus ensuring that even in his passing, Eisav would not lose the opportunity for spiritual redemption.

To summarize, the midrash states that Yaakov chose to send divine malachim to Eisav to announce his arrival, rather than relying on human messengers. Zera Shimshon interprets this as Yaakov’s profound desire for Eisav to repent for his misdeeds. Recognizing the powerful impact of his words, and those of all tzaddikim, Yaakov preferred a malach to convey his message—as they could transmit not just the meaning, but the words themselves which are very powerful. This strategy increased the likelihood of Eisav engaging in teshuva.

Zera Shimshon further clarifies that Yaakov’s concern for Eisav’s repentance had a dual purpose. Firstly, it was to ensure Eisav could no longer pose a threat to Yaakov. Secondly, given Eisav’s deep involvement in Avodah Zara and other transgressions, his repentance would likely lead to his demise—a consequence that could paradoxically grant him a place in Olam Haba.

Even if, thankfully, none of the readers of this dvar Torah are confronted with a situation as extreme as being endangered by a sibling, the insights from Zera Shimshon’s teachings can profoundly influence our daily interactions. In our lives, we frequently meet people who might not align with our preferences or whose behaviors might cause us discomfort or annoyance. It’s essential in these moments to recall that these individuals—despite our differences—share a common lineage with us as descendants of Avraham, Yitzchak and Yaakov. This shared heritage bestows upon them—just as it does upon us—an inherent kedusha (holiness), a spiritual dignity that we are called to acknowledge and respect.

This perspective is not just about tolerating others but recognizing the sanctity inherent in every person. Therefore, even when our natural inclination might be to avoid such individuals—when life’s circumstances lead us to interact with them—it’s not only important but imperative to engage with respect and understanding. More so, there is a deeper responsibility involved—to assist and encourage them in their spiritual journey, just as we seek growth in our own spiritual journey. By doing so, we not only honor their inherent kedusha but also contribute to the collective spiritual elevation of klal Yisrael, drawing from the rich spiritual legacy of our forefathers.

HaRav Shimshon Nachmani—author of Zera Shimshon—lived in Italy, about 300 years ago, in the time of the Or HaChaim HaKodesh. He had one child who died in his lifetime and, in the preface, he promises that those who learn his sefarim, “will see children and grandchildren like the offshoots of an olive tree around your tables.”