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

On this pasuk, the midrash comments, “Messengers: human messengers… Rabbanim say that they were heavenly messengers, melachim (angels). Rabbi Chamma ben Chanina said, ‘(We can understand why Yaakov merited to have heavenly messengers (malachim) assist him with the following logic:) If five malachim appeared to Hagar, who was merely the maid servant of Sarah, then it is certainly reasonable that they came to aid Yaakov, who was a beloved family member.’”

(Another proof:) If Eliezer — who was merely the servant of Avraham’s family — merited malachim, when he went to look for a wife for Yitzchok, then it was certainly reasonable that they should come to assist Yaakov, who was a beloved family member. Rabbi Yossi said, “If three malachim assisted Yosef — who was the youngest of the tribes — then, surely, Yaakov — who was the father of the tribes — surely deserves to merit malachim.”

The Zera Shimshon asks: Why did Rabbi Chamma ben Chanina and Rabbi Yossi bring proofs from Hagar, Eliezer and Yosef that Yaakov merited heavenly messengers and not human ones? It is written in the two pesukim, before this pasuk (the last two pesukim in parshas Vayeitzei): “And Yaakov went on his way and angels of Hashem met him… And Yaakov said: ‘This is a Godly camp,’ and he called the place, ‘Machanayim.’” From these pesukim, we learn that a camp of heavenly angels came to Yaakov. Therefore, it stands to reason that when messengers are mentioned in the next pasuk — it is referring to those messengers — and there is no reason to bring a proof to this from Hagar, Eliezer and Yosef. It is the simple peshat of the pesukim!

He answers in light of the midrash (Yalkut Shemoni, remez 130) that infers from the fact that when Yaakov saw the group of melachim that came to meet him, when he entered Eretz Yisroel, he said that this is a “Godly camp” that there were 600,000 melachim in this camp — since the Shechinah only rests, when there are that many beings.

Therefore, the Zera Shimshon reasons that it wouldn’t be proper for Yaakov to send any of those melachim to Eisav, because this would cause the Shechinah to go away. Since the messengers that Yaakov sent to Eisav were not from the malachim that met him when he entered Eretz Yisroel, the midrash brings sources they were also angels and not human messengers.

The Zera Shimshon asks another question: Why did Yaakov send melachim to Eisav and not just regular human ones? Why weren’t humans able to talk to Eisav, just like the angels did?

A possible answer is that Yaakov wanted to know if Eisav still hated him or not? A human can’t really know what the true feelings of another person, but a malach can. Therefore, Yaakov sent a malach and not a human.

The Zera Shimshon rejects this reason — though — because a malach doesn’t have to go to a person to know this, but can find this out — even if he is not next to that person! We find an example of this with the malachim who assisted Yosef. They told Yosef his brother’s feelings toward him, even before Yosef met them.

Rather, he explains the reason he sent angels and not humans in light of the midrash that explains the reason that Yaakov sent a messenger to Eisav at all was in order that Eisav will repent and do teshuvah on all the bad that he did in his lifetime. Therefore, Yaakov sent malachim instead of a human, because malachim are more effective to persuade and influence others than humans.

A question still remains, though, why was Yaakov interested in making Eisav a baal teshuva at all?

The Zera Shimshon gives two reasons for this:

Firstly, the Gemara (Avodah Zara 17a) learns from the pasuk in Mishlei (2:19), כׇּל־בָּאֶיהָ לֹא יְשׁוּבוּן וְלֹא־יַשִּׂיגוּ אׇרְחוֹת חַיִּים׃, “Whoever comes to it will not return, and will never find the path of life,” that whomever is strongly involved with avodah zara or has a high position of authority and abuses it, even if he does teshuva, he will “never find the path of life,” meaning, he will die soon after.

Chazal teaches us that Eisav served avodah zara and it is also written in the midrash that Eisav went to Mitzrayim to purchase the rights to collect taxes. Therefore, since Yaakov was constantly afraid that Eisav would harm or kill him, he wanted him to do teshuva on his involvement with avodah zara and taking taxes from people, in order that he would die and Yaakov would no longer have to fear him.

Another reason the Zera Shimshon writes is, simply, that Yaakov wanted his twin brother to do teshuva, so that he would also merit Olam Habah.