(18) You shall appoint leaders and officers for your gates, in all the settlements that your God יהוה is giving you, and they shall govern the people with due justice.
In the simple understanding the Torah is teaching that there is a mitzvah to appoint judges and law enforcement upon a Jewish society.
(א) היא שצונו למנות שופטים ושוטרים שיכריחו לעשות מצות התורה ויחזירו את הנוטים מדרך האמת אליה על כרחם ויצוו לעשות טוב ויחזרו מהרע ויעמידו הגדרים על העובר עד שלא יהיו מצות התורה ואזהרותיה נדונות לפי אמונת כל איש...
That is that He commanded us to appoint judges and officers to force the implementation of the Torah's commandments and to bring those inclining away from the true path back towards it. And they will command to do the good and to come back from evil and will establish fences for the transgressor, such that the commandments and prohibitions of the Torah will not be decided according to the beliefs of each individual...
The connection between “leaders and officers” and the two parts of the tefillen isn’t so arbitrary if we give it some thought. When we don our head-tefillen, we are essentially “appointing” ourselves as a leader to inculcate those ideas of the Torah that lay within the boxes of the tefillen.
(Pro tip: The portions of the Torah which appear in the Tefillen boxes is conveniently found in the siddur where the blessings of the Tefillen are also found)
(This is such basic knowledge to the the Torah, that in society there is a whole new department, and in the tefillen there is a whole new compartment!)
This is because the goal of a Jew (and a Jewish society as a whole) is to achieve complete mastery over oneself and full devotion to Hashem. Jewish life is about constantly making decisions through this "apparatus":
MO’ACH (Mind) refers to the intellectual study of the Torah and rational decision making based on one’s learning.
LEV (Heart)- refers to forcing those ideals into your heart through learning Mussar and working on ones character.
C'LAYOS (Limbs) refers to bringing those inculcated ideals down to all of one’s actions.
עשרה דורות מנח ועד אברהם וכי מה צורך לבאי עולם בכך אלא ללמד שכל אותן הדורות היו מכעיסין לפניו ולא היה אחד מהם שיהלך בדרכי הקב״ה עד שבא אברהם אבינו והלך בדרכי הקב״ה שנא׳ (בראשית כ״ו:ה׳) עקב אשר שמע אברהם בקולי וגו' (וכי תורה אחת שמר והלא תורות הרבה שמר) אלא מלמד שזימן הקב״ה לאברהם אבינו ב׳ כליותיו כשני חכמים והיו מבינות אותו ויועצות אותו ומלמדות אותו חכמה כל הלילה שנא׳ (תהילים ט״ז:ז׳) אברך את ה׳ אשר יעצני אף לילות יסרוני כליותי.
There were ten generations from Noah to Avraham. And why was it necessary to bring all those people into the world? But this is to teach us that all those generations continued to anger God, and there was not one among them who walked in the ways of the Holy Blessed One until Abraham our forefather came along, and he walked in the ways of the Holy Blessed One, as it says (Genesis 26:5), “Because Abraham heeded My call [and kept My charge, My commandments, My rules, and My Torahs.]” (But there is only one Torah! How could he have kept Torahs, plural?) This teaches that the Holy Blessed One planted two inner voices in Abraham, like two wise men, who helped him understand, advised him, and taught him wisdom all night long, as it says (Psalms 16:7), “I will bless the Eternal who has advised me. Even at night, the voices inside of me [lit., my kidneys] have admonished me.”
But according to this understanding we can say it means that WE need to be kings over ourselves in the world, in the field - this is the month where we need to recalibrate this truth within ourselves and act accordingly.
Our Avodah (mission) of Elul is appoint the “Shoftim and Shotrim” (leaders and enforcers) over ourselves, to create a burgeoning Torah "society" within ourselves.
Good Shabbos!
A big yasher koach to Rav Shimon Grady, our esteemed Rav, for providing the wonderful content of this weeks Dvar Torah through a series of voice notes :)