The following is a brief summary of a thought said over by R' Frand in his shiur this evening. I have attempted to reproduce this vort to the best of my ability. Any perceived inconsistencies are the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
The Medrash notes that the words "Lech Lecha" appear twice in the Torah. The first occurrence is in this week's parsha where Hashem instructs Avraham Avinu to go to Eretz Kina'an. The second time that the words are used is in conjunction with the akeidah where Avraham is told in Bereishis 22:2 to take Yitzchak "V'Lech Lecha el Eretz HaMoriah." R' Levi then says that he does not know which of the two directives which Avraham obeyed are more dear to Hashem.
Rashi answers the question posed by R' Levi, stating that Avraham's act of going up to bring Yitzchak as a sacrifice was the act which was more dear to Hashem.
Many times it seems to the casual observer that Rashi is stating the obvious, but on further review there is a deeper level which demonstrates Rashi's genius. In the matter at hand, Rashi's answer seems obvious - of course the act of potentially sacrificing one's child is a greater act then merely leaving the land of one's birthplace.
In answering this question, R' Frand made reference to a series of halachos mentioned by the Rambam in Hilchos Avodas Kochavim (1: 1-3). In describing how man sunk to the depths of worshiping idols, the Rambam explains that people originally wanted to show honor to the sun, moon or stars because they recognized that they were performing tasks designated by Hashem. However, people lost sight of the fact that these objects were merely carrying out jobs assigned by Hashem and instead the people began to worship the objects. Avraham realized that the world had to have been created by a being which created the order of the universe. At the time, Avraham did not have a Rabbi/teacher to explain things to him as he was stuck living in Ur Kasdim among the idol worshipers. Nevertheless, Avraham developed his understanding of Hashem and began to influence others. This earned the ire of the king who had Avraham thrown in a fiery furnace. Of course, Avraham survived and subsequently left Ur Kasdim and began to travel the area explaining the concept of Hashem and bringing people to understand Hashem's role in the world.
Given this preface, ask yourself about the following scenario. A Rabbi goes to a small city where there are few observant Jews and he begins to bring those who have drifted away back to Judaism. He becomes very successful at his task and suddenly people are coming to synagogue and he begins to influence non-observant Jews in surrounding communities to also return to the fold. After some time, the Rabbi receives a call from a large Jewish community which has learned of the Rabbi's talents and would like him to come and become the Rabbi in their metropolis. What should he do?
This was the quandary facing Avraham. He had managed to bring many people back from idolatry and was teaching them the meaning of Hashem. Suddenly, Hashem tells him to leave this geographic area and all that he accomplished there and move to Eretz Kina'an. Avraham looks at all this and asks - should I leave this behind? This is the meaning of the question in the medrash and why we need Rashi to answer the question.
A proof can be found in the first pasuk of Vayera. The Torah recites that Avraham was at Elonei Mamreh. Why is the area named after Mamreh? Because when Hashem told Avraham to give himself a bris millah, Avraham wondered whether he should follow the order and he asked Mamreh for guidance. Mamreh told him to follow the command of Hashem. As a result, Mamreh is rewarded.
The questioning by Avraham seems bizarre - did he really not know whether he should listen? When viewed in the light of the above Medrash, we can have a better understanding of the question. Avraham was commanded to perform a bris which would forever mark him as different from all others. If he performed the bris in a public way, he thought, maybe the people I am trying to influence will view me as different and they will be less likely to listen when I tell them about Hashem. Faced with this question, he went to Mamreh for advice.
One final example of Avraham's work before he left for Eretz Kina'an can be seen from the gemara in Avodah Zarah. The gemara explain that the world will last up to 6,000 years. The first two thousand will be tohu, the second two thousand will be Torah and the third will be the time of Moshiach. When does the era of Torah start? When Avraham begins to be mikarev people. [It is known that Avraham was born in 1948 and that he recognized Hashem at 40].
R' Weiss asks on this gemara - but there was Torah before Avraham. Indeed, Noach observed laws and there even were the Yeshivos of Shem and Aver. He answers by mentioning the Kesef Mishneh who says that there was Torah, but Avraham was the first to bring the masses in to learn it. The yeshivos of Shem and Aver existed for those who traveled there to learn. Avraham went out to teach, thus he is credited with commencing the era of Torah.
With this understanding, we can see the dilemma facing Avraham when he was told "Lech Lecha" and why the Medrash's question does not have such an obvious answer.
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