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"A Quiet Man, Living in Tents"
Jacob and Esau were born with disparate natures, and these natures are unveiled before us as they grow: "And the boys grew; and Esau was a skillful hunter, a man of the field; and Jacob was a quiet man, living in tents" (Genesis 25:27). Onkelos translates this description of Jacob's nature thus: "a perfect individual who served in the study hall," i.e., Jacob would sit and study Torah in the study hall that existed in that age.
Esau was "a man of the field" and embodied the fulfillment of the Adam's curse: "By the sweat of your brow shall you eat bread" (Genesis 19:19). The students of the study hall, however, were exempt from this decree and their livelihood came to them through others. Hence we find (in Genesis 14:18-20) that Abraham gave "a tenth of all" to "Melchizedek king of Shalem" who was "a priest of the highest God." Targum Yonatan informs us that this Melchizedek is in fact Shem, the son of Noah, and the Sages mention in several places that the patriarch Jacob learned in the "Yeshiva of Shem and Eber."

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The role of these "priests of the highest God" was to cause people to better their ways and to prepare their hearts to serve God. They would reveal to people that when humankind rectifies its sins and worships the Creator, the world will become illuminated and a new era will begin, one in which the punishment of toil will be nullified. This period is also called the "Messianic Era," and Rambam (in Hilkhot Melakhim 12:5) explains that when it arrives, "goodness will be greatly increased, and pleasures will be as available as the sand, and the entire world will be engaged in nothing but the knowledge of God."
Indeed, Jacob did not spend his entire life in the study hall. After some time, he left and went abroad and made a living there from the toil of his hands, and was a faithful reliable laborer. But Jacob only did this because he was compelled to, and when he returned to the land of Israel, he wished to return to what he had done previously, to sit in the yeshiva and to serve in it as a priest of the highest God.
"And Settle There"
When Jacob fled the land of Israel, he made an oath at Bet-El which he would fulfill upon his return to the land (Genesis 28:22): "And this stone, which I have set for a pillar, shall be God’s house; and of all that you shall give me I will surely give the tenth to you." After the events of Shechem, the Almighty reminds Jacob of his vow (ibid. 35:1): "And God said to Jacob, rise up and go up to Bet-El and settle there, and make an altar there to the God Who appeared to you when you fled from Esau your brother."
And we need to clarify why it is that the Almighty reminds Jacob of the vow of the building of the altar but does not remind him of the vow of the tithe? Furthermore, where do we find that Jacob fulfilled the vow of the tithe, and to whom did he give it? Indeed, nowhere does the plain text tell us that Jacob fulfilled the vow of the tithe. And since we cannot suspect Jacob of having broken his vow, we must conclude that he did not mean to give tithes from his property to the study hall of Shem and Eber, but rather to dedicate himself and all of his possessions to sacred ends.
The number ten, which was chosen to serve as the basis of the various tithes mentioned in the Torah, implies a connection with the sacred and with the heavenly realm. And we indeed find in the tract of Menachot (29b) that the upper world was created through the Hebrew letter "yod," which is the tenth letter in the Hebrew alphabet. We also find in Berakhot (21b): "Where do we learn that an individual is not permitted to recite kedusha [without a quorum of ten]? We learn it from the verse, 'I will be sanctified in the midst of the children of Israel' - i.e., no matter of sanctity shall be [carried out with] less than ten."
When Jacob made his tithe vow, his intention was to dedicate himself, his family, and all of his property to the realm of the sacred - i.e. to sit in the study hall and serve God as a family of priests. They would be like Jacob at his outset, a "dweller of tents." In a like manner, we find (Numbers 3:45) that after the Levites and their property were dedicated to the service of the sanctuary they no longer had to be redeemed from the priest.
The Almighty tells Jacob to "get up and go to Bet-El," and then adds "and settle [lit. 'sit'] there." By adding this latter command God is in fact reminding him of the vow of the tithe. This is because the tithe, which implies a bond with sanctity, is expressed in "settling"—i.e., sitting—in the study hall. This explanation receives support from Ramban, who writes: "I do not know what is meant by 'and settle there'... Perhaps He commanded 'and settle there' in order [that he should] direct his thoughts to clinging to God." We have clarified, then, that the state of "settling," in which they sat and directed their thoughts to clinging to the Almighty, was the practical expression of the fulfillment of the tithe vow.
The Struggle Over the "Man"
In Scripture, a teacher of Torah and faith is sometimes called a "malakh," an angel. Here the son asks: Will the vow that his father makes cause the son to want to live like an angel? And what will the boy do when his soul continues to desire the worldly life of a normal "man" and does not desire to be in the study hall and to live like an angel?
The Talmud (Hullin 91a) brings R' Elazar's interpretation of the verse "And Jacob was left alone; and a man wrestled with him until the break of day" (Genesis 32:25): "R' Elazar said: He remained behind because of some small jars. Hence [we learn] that the righteous' property is dearer to them than their body; and why is this? Because they do not stretch out their hands to robbery."
A simple understanding of this interpretation tells us that Jacob knew he was endangering his life when he remained alone, yet he nonetheless took this step in order to save a bit of his property. Yet this is difficult to accept; after all, the Talmud (Hullin 10a) teaches us that a person must be extra cautious when it comes to human life and beware of every possible danger. If so, just as the righteous need to be stringent and on guard of possible theft, so they need to be careful of any possible danger. So why, then, did Jacob endangered himself for those "small jars"?
These "small jars" may be viewed as a parable. Jacob foresaw that amongst his sons or grandsons there would be "a man" who would not want to live in the study hall. To the contrary, "Esau's minister" will pull at this boy to join him and to nurture the physical and material aspects of his life. Jacob did not want the boy who desired to be a "man" to feel that he was not "an angel," to be seduced into joining to Esau. Jacob did not want to forgo the "small jars," i.e., the "men" whose Torah aspirations seem small, and he struggled to have them remain together.
Jacob informs the "man," that this nation, whose destiny it is to bring redemption to the world, is also in need of "men" - i.e. people who work and toil and focus on developing the physical, non-Torah sides of existence. People who see the life of the soul as the "body" and the center of their nation, who gain pleasure from the pursuit of the "body," such people are righteous. But those who love their property more than their body, i.e. that prefer to deal in the material, physical side of the nation and carry out their dealings with integrity, these people are also righteous - "and your nation, all are righteous!" (Isaiah 60:21).
Jacob the "man" abandoned his thoughts of passing Esau's minister and decided to remain "with him" - i.e., to remain with Jacob the "angel," to join him in a journey to bring redemption to the world, a journey that will last "until the break of day."
Where there are no men, "strive" to be a "man"
Yet, if "Your people are all righteous" (ibid. 60:21), how can one who belongs to the nation of the children of Jacob choose his own path in life? Rabban Gamliel, the son of R' Yehudah the Prince, provides us with an answer to this question: "He would say... nor do all who engage in much business becomes wise, and in a place where there are no men, strive to be a man" (Avot 2:5). Rashbatz (R' Shimon Duran), in his Mishnah commentary, "Magen Avot," explains the words of Rabban Gamliel as follows: "Nor do all who engage in much business becomes wise" - being engaged in business prevents a person from engaging himself in Torah "And in a place where there are no men, strive to be a man" - Onkelos translates the words "A man wrestled with him" thus: "A man strove [ve-ishtadel gavra] with him"... That is, in a place where there are no men to fill in the breach, to engage in communal needs, "strive" to be a man, even if it means neglecting the words of Torah... and the Sages say (Menachot 99): "Sometimes the neglect of Torah is its own foundation... "
Rashbatz, then, informs us that the Mishnah has in mind Jacob's struggle with the "man" according to Onkelos' Aramaic translation - "ve-ishtadel gavra." Rashi explains that the word "ve-ishtadel" in Aramaic can also mean 'enticed', so that the verse reads, "A man enticed him." However, we still have to clarify the meaning of this "enticement" Scripture speaks of.
According to the Rashbatz, a war was waged over a certain "man" among Jacob's offspring. Esau's minister told him that, inclined as he is to be a "man," he ought to part with Jacob's sons, all "angels," and cross over to the sons of Esau. Jacob, on the other hand, suggests that he remain a "man" within the nation of the Jacob's children. This struggle concludes with his being enticed to remain a "man" among Jacob's children.
The Mishnah teaches us to learn from Jacob's struggle that the only path to be rejected is that which leads to becoming a "man" of the sons of Esau. Yet, being "enticed" into becoming a "man" of the sons of Jacob can contain a measure of righteousness. Certainly priority goes to being an "angel" who diminishes business and increases Torah, but when the nation cries out for a helping hand and there are not enough "men" to tend to the task, Rabban Gamliel advises the "angel" to be enticed into leaving the study hall and becoming a "man" for the sake of the community.
In sum, we have seen that Jacob's tithe oath implied a bond with all that is sacred, and its practical expression would be achieved through "sitting" - the sort of sitting which involves Torah study. We further saw that the "small jars" and the "righteous whose property is dearer to them than their body" represent people who do not engage much in Torah but instead prefer to deal with the material, financial aspects of the nation of Israel. Finally, we have seen that the tales of the Sages evince a spirit of favorable judgment, and they teach us that our forefather Jacob understood the need to embrace such "righteous" people in order to bring about the redemption.

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