Based on what we have learned, we will now establish the connection between this week’s parsha, parshas Shoftim and the month of Elul. It is evident that the command to appoint judges and officers is intimately related to our current discussion. Undoubtedly, there is a grave concern that a person will arbitrarily decide on his own what is proper and what is not and act accordingly. After all, “A man’s every way is upright in his eyes.” Therefore, HKB”H commanded us: "שופטים ושוטרים תתן לך בכל שעריך אשר ה' אלקיך נותן לך לשבטיך"—to appoint and station judges and officers to monitor us and guide us to follow the proper path. As a result, we are assured: "ושפטו את העם משפט צדק"—that we will follow a just path and not be led astray by the yetzer hara who portrays an aveirah as a mitzvah.
This explains beautifully the continuation of the passage. It continues with the stern warning (Devarim 16, 19): "לא תטה משפט לא תכיר פנים ולא תקח שוחד כי השוחד יעור עיני חכמים ויסלף דברי צדיקים"—you shall not pervert judgment, you shall not display favoritism; and you shall not take a bribe, because bribery will blind the eyes of the wise and distort the words of the righteous. Since the purpose of appointing judges is to teach Yisrael the ways of the Torah and to prevent them from being led astray by the yetzer that perverts their intellect to perceive an aveirah as a mitzvah. Therefore, the judges must take great care not to accept bribes. For, it is inevitable, chas v’shalom, that bribery will blind them and pervert the wheels of justice. Then, they, too, will fall prey to yetzer and distort the words of the G-d of life.
Now, to the connection between parshas Shoftim and the month of Elul, the month of teshuvah. We learn from the Bnei Yissaschar (Tamuz-Av 1, 6) in the name of the Megaleh Amukos on Vaeschanan (107), brought down in the name of the Zohar hakadosh (Yisro 78b), that Yaakov and Eisav agreed to divide up the months of the year between them. Yaakov Avinu took as his portion for the realm of kedushah the first three months—Nissan, Iyar, and Sivan. The exodus from Mitzrayim took place in Nissan; they then prepared themselves during the days of the Sefirah during the month of Iyar to receive the Torah; in Sivan, they received the Torah at Har Sinai.
Correspondingly, Eisav chose the following three months as his portion—Tamuz, Av, and Elul. He was elated that he had control of the month of Elul, since he could prevent Yisrael from performing teshuvah prior to the Days of Judgment. However, Yaakov Avinu employed various tactics waging a spiritual war against Eisav to gain possession of the month of Elul—even though it seemed to rightfully belong to Eisav. Without a doubt, Yaakov did not do so without justification. Seeing as Yaakov succeeded in the battle, it must have been condoned from above. So, how, indeed, did Yaakov justify taking the month of Elul away from Eisav?
As mentioned, Eisav was elated when given the opportunity to prevent Yisrael from performing proper teshuvah during the month of Elul. For, when a Jew recognizes that he has sinned against his Maker, he will most certainly try to make amends and mend his relationship with his Father in Heaven. So, when the month of Elul fell to him, Eisav figured that he could prevent Yisrael from performing teshuvah by perverting their perception and convincing them that they had not sinned. Foreseeing this, Yaakov battled Eisav to gain possession of the month of Elul to enable Yisrael to perform proper, sincere teshuvah.
