“And it shall be for you a sign on your arm and a reminder between your eyes – in order that Hashem’s Torah may be in your mouth – for with a strong hand Hashem took you out of Egypt” ^(Shemot 13:9)
“Bind them as a sign upon your arm and they shall be ornaments between your eyes” (Devarim 6:8)
“You shall place these words of Mine upon your heart and upon your soul; you shall bind them for a sign upon your arm and they shall be an ornament between your eyes” (ibid. 11:18).
&“Then all the peoples of the earth will see that the Name of Hashem is called upon you, and they will fear you” (ibid. 28:10)
>Rabbi Eliezer Hagadol says that this refers to the tefillin worn on the head (Berachot 6a).
Our Sages ask, “Who is considered an ignoramus?” Rabbi Yehoshua answers, “One who desists from wearing tefillin” (Berachot 47b).
Rabbi Yanai asserts that tefillin must be worn only on a clean body, like that of Elisha Ba’al Kenafayim. Why was he called Ba’al Kenafayim (lit. the one who had wings)? The Gemara relates (Berachot 49a) the following fascinating narrative: The wicked Roman emperor decreed that whoever would don tefillin would be pierced through the skull. Elisha would wear tefillin in the marketplace. A Roman legionnaire once found him and began chasing after him. When he finally reached Elisha, Elisha hastily removed his tefillin and held them in his closed hands. “What are you holding?” the Roman asked.
“The wings of a dove.”
Elisha opened his hands, and lo and behold! a white dove flew out. From then on, he was called by the fitting appellation of Elisha Ba’al Kenafayim.
There are seven categories of people who are cast aside by Heaven. Those who do not wear tefillin on the head or arms, or tzitzit on their clothes, and those who do not have a mezuzah on their doorposts… (Pesachim 113b).
The Ramban states (HaEmunah V’Habitachon 22): Since the heart is the main organ of a person, it was determined that the sign should be placed upon the heart. And we have a reminder between the eyes, because when a person sees something, it remains with him and he remembers it. Proof of this is the fact that the mitzvah of tefillin is relevant only by day, when one can see them.
The reason why the tefillin is placed upon the left arm is that the power of tefillin derives from the left side, similar to the etrog which is held to the left of the lulav. But I disagree. I think that the tefillin of the head is worn upon the brain, since the neshamah derives its strength from the mind. And the reason the tefillin are worn on the left arm is because this side is across from the right side of Hashem, so to speak. Regarding the etrog, it is held on the left for a completely different reason; regarding the amount of water we will receive…
The Sefer Hachinuch (Mitzvah 421-422) writes: Since man is physical, he is naturally drawn after materialistic urges. It is only natural for something material to seek pleasure, like the unintelligent horse and mule. It is only the spiritual soul which Hashem implanted in man which prevents him from falling into sin. Hashem wants to give merit to His holy nation. Therefore, He commanded us to place guards around our neshamah. These are the words of the Torah, which should never cease, day and night. Similarly, placing four tzitzit on the corners of our garments and a mezuzah on our doorpost, as well as tefillin on our arms and heads provides us with spiritual protection.
The four parshiyot contained in the tefillin affirm our acceptance of the yoke of Heaven and the oneness of Hashem. They also describe the Exodus of Egypt, which demonstrates belief in the Creator and His supervision of this world. These are the foundations of the Jewish religion. Therefore, we are adjured to place these reminders between our eyes and upon our arms. Scientists state that these organs are the bed of the intellect. By placing the tefillin specifically on these parts of our body, we become strengthened in our faith and maintain reminders of Hashem’s ways and merit eternal life.