אחרי הכתו את סיחן מלך האמרי אשר יושב בחשבון ואת עוג מלך הבשן אשר יושב בעשתרת באדרעי. Why does the possuk emphasis the rebuke of Moshe was said only after סיחון ועוג were conquered.
As with everything else, the conquest of the nations of Eretz Yisrael and of Sichon and Og represent a spiritual fight for every individual according to the chassidic books.
The chassidic seforim say that the 7 nations of Eretz Yisrael each one represents one of the 7 middot which is optimized by one of the nations. The final three nations conquered only in the times of the Mashich represent the three facilities of the brain which can be purified only in the days of the future. Where do Sichon and Og fit on the map?
Rav Tzaddok says that Sichon מלך חשבון, bearing the same word as calculation is the power which goes against the kedusha of the brain of a person. Og the king of בשן אשר יושב בעשתרות באדרעי is the power against a person's heart, היינו לעשות את הלב כאבן לבל להתפעל בדברי תורה, ועל זה רומז רש"י ז"ל עשתרות, לשון צוקין וקשים כמו עשתרות קרנים. The Sfas Emes cites his grandfather, the Rim, that is why it is only after the killing of the Sichon and Og, when the hearts and minds of Klal Yisrael were opened could that the mussar of Moshe could be heard. He adds that we wear the tefillin of the head and the hand to counterbalance the Sichon and Og powers and open our hearts and minds. בשם מו"ז ז"ל על פסוק אחרי הכותו שקודם זה לא הי' יכול להכניס הדברים בלבם של ישראל. שהמה היו קליפות גדולות. סיחון מלך חשבון שורש המחשבות רעות ונגד זה תפילין של ראש. עוג בעשתרות באדרעי המעשה ונגד זה תש"י כו' עכ"ד (5640).
The Midrash Shir Hashirim (4:3) says all those that went to fight against Midyan never erred and wore the tefillin of the head before that of the hand. Why was this a prerequisite for the war against Midyan? The Nesivos Shalom explains that the war against Midyan was waged to fight against the tumah that Midyan pervaded against the heart with the seduction of their daughters and of the mind for they convinced them to serve avodah zarah. The tikkun must go in the same order as the problem, fix the heart and afterward the mind, tefillin shel yad followed by tefillin of the head.
The possuk in Vezos Haberacha says וּלְגָד אָמַר בָּרוּךְ מַרְחִיב גָּד כְּלָבִיא שָׁכֵן וְטָרַף זְרוֹעַ אַף קָדְקֹד. The Daat Zekanim says פי' הרב בכור שור כי כשהיה מכה והמוכה מגביה זרועו שלא יכה בראשו היה חותך הזרוע שלפני הראש והראש עמו ומעמיק המכה עד סוף הכתף. What is the purpose for this greatness to be able to knock off the head and arm with one blow? The Gra says since warriors have to be careful from sin, even so slight as talking between the tefillin of the hand and the head, they had no separation therefore middah keneged middah they chop off the head and hand in one fell swoop. The people of shevet Gad have control over their minds and hearts.
This is why it is the people of Gad and Reuvain who are the head and hand masters are the ones to take over the lands of Sichon and Og who are the dark side of the head and heart. That is why the parsha of Gad and Reuvain follows after the war against Midyan (Rav Baruch Rosenblum.)
The Shem MeShmuel Vayetza adds that Og himself is a power that goes against the heart and head, וי"ל דכמו שאדרעי מלשון דרועא מקביל לתפלה של יד, כן עשתרות קרנים שקרנים הוא בגובה הראש, היא קליפה מקביל לעומת תפלה של ראש, כי תפלה של ראש הוא כמו קרנים בגובה הראש. The Gemarah Berachot (54b) says that Og took a rock of 3 parsa and was going to drop it on Yisrael but the grasshoppers came and were eating away the rock and his teeth were widened so he couldn't drop it. Rabbi Pinchas Freidman says the three parsa are the three facilities of the bread that Og wanted to contaminate. Why is it his שיניים, his teeth which do him in? The Bnei Yissascher (Nissan maamer 5 siman 14) says that it is the tooth of the rasha which became elongated because the letters of רשע have the bad letters of רע in them but the letter ש with three prongs corresponding to the three Avot is a letter of holiness dragged along with the רע. When the ש, the שני רשעים is broken the רע is left to be discarded. It is the ש engraved on the tefillin of the hand and the head which counteracts the power of Og.
However, it still needs to be explained what is the difference between the battles of Sichon and Og and those against the nations of Eretz Yisrael? Sichon and Og are the gatekeepers of Eretz Yisrael. Even before one wishes to purify their heart and mind, they first must be opened up. ומלתם את ערלת לבבכם, the heart has to be opened. That is what the battle of Sichon and Og is about, to open the gateways to the minds and hearts to allow them to be filled with holiness.
כל המתאבל על ירושלים רואה וזוכה בשמחתה. The Kedushat Halevi says that זוכה can mean זכות, purified. One who purifies themselves will be able to see Yerushalayim. Only after opening one's heart can one merit to see Yerushalayim.
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