“And he stayed there that night, and he took from what came into his hand a gift for Esav his brother.” (Bereishit 32:14)
In the Midrash (Yalkut Shimoni, Parashat Vayishlach, remez 133), it is taught that Yaakov took all the tithe (maaser) of his livestock and sent it in the hands of his servants to give to Esav. HaKadosh Baruch Hu said to him: “You made the sacred profane. [You took the maaser, which is consecrated for holy matters, and gave it as a gift to Esav, in whom there is no holiness whatsoever].” Yaakov responded: “Ribono shel Olam, what I separated was to flatter the wicked one so that he would not kill me.”
It is appropriate to ask: Why did Yaakov send precisely the tithe, and not assets of his personal property?
To explain this, it is worth recalling that, from the beginning, when Yaakov left the Land of Israel and headed to Charan, he had the dream of the ladder and the revelation of Hashem, Who promised to guard him on all his way. When he awoke, Yaakov made a vow to separate the tithe. The intention of this vow was to tithe all the possessions he would acquire outside the Land of Israel, since by being under the jurisdiction of foreign spiritual forces, it was appropriate to give them a portion to prevent them from accusing him. Thus writes the Siftei Kohen commentary (on the verse “and he put it into the hands of his servants,” citing the Zohar) regarding the two he-goats of Yom Kippur: one for Hashem and one for Azazel.
For this reason, when Yaakov woke up from the dream of the ladder and made the vow to separate tithes, he doubled his expression saying: ”aser, aaserenu Lach” ('I will tithe, tithe it for You') (Bereishit 28:22), hinting at two deliveries: one for Hashem and one “for Azazel.” This is hinted at in the rhythmic cantillation accents (taamei hamikra) of the Torah reading found on the words of this phrase in Hebrew: below the word ”aser” is the Tarcha accent (or also called Tipecha), which indicates an interruption and separation from the text that follows, ”aaserenu Lach”. This implies that Yaakov had made a vow to separate two tithes: the maaser that is “profane” — which he would end up giving to Esav, and which was separated from the maaser he was going to give for Hashem — and the maaser “kodesh,” which was consecrated for Hashem.
There was no sin in this on Yaakov's part, as this had been his intention from the beginning. However, Hakadosh Baruch Hu still said to him: “You made the sacred profane,” because he should not have called what he sent to Esav “tithe.” Furthermore, he should not have mentioned both expressions together in such a way that it would seem that both ”aser” and ”aaserenu” would be ”Lach,” for Hashem, giving rise to the suspicion that Yaakov had given Esav something he had promised to dedicate to Hashem.
Yaakov responded to Hakadosh Baruch Hu by saying that before the possessions come into the person's domain, the name “tithe” does not yet apply. Therefore, when he said “and of everything You give me, I will surely tithe it for You,” the tithe did not yet exist: it would only become tithe once he received it and set it aside. And at the moment of setting it aside, by explicitly stating that it was to be handed over to Esav, it would be clear to everyone that his intention in saying ”aser” was solely to appease him so that he would not kill him, by giving him a generous portion called “tithe” (similar to the he-goat sent on Yom Kippur to Azazel to “appease” him and prevent him from accusing Israel). Everyone would know that it was not truly a tithe; he was not giving him anything from the tithe that belonged to Hashem.
Zera Shimshon, Parashat Vayishlach, Art. 4
