Why Do Don Tefillin on the Left Hand, Normally We Treat the Right Hand With More Importance

In this week’s parsha we have the pasuk:והיו לאות על ידכה ולטוטפות בין עיניך - “And it shall be for you a sign on your arm and a reminder between your eyes. (Shemos 13:9)

The Gemara expands the wordידכה , to יד כהה and learns that the tefillin shel yad should be placed on the weaker hand, i.e. the left. Normally when it comes to carrying out mitzvos we do them with the right hand, and generally in halachah we treat the right hand with more importance, so why is it, that when it comes to the special mitzvah of tefillin we don’t, we see to give more importance to the left hand?

The Meforshim offer a number of different answers:

1. The Chizkuni answers, that the right hand is always busy, when passing and receiving things one normally uses the right hand, since the right hand is busier than the left, it’s more fitting to don the tefillin on the left.
2. The Chizkuni offers a second answer, which is that we want the right hand to be available to fulfill the mitzvah of tying the tefillin (וקשרתם לאות על ידך), since we want the right hand to be used when tying the tefllin, the tefillin must be placed on the left arm.
3. The Kli Yakar answers that putting tefillin on our weaker hand symbolizes that without the help of Hashem, we are weak and don’t have power to accomplish anything on our own. Keeping this in mind as we start every day gives us the strength and faith to stay on the straight path throughout the day, knowing that ultimately all is in the hands of Hashem.
4. The Kli Yakar offers a second explanation, which is that the right side represents physical desires and strength, while the left, weaker side represents the (more restrained) spiritual and intellectual strength. Wearing tefillin on the left side demonstrates that it is the spiritual and intellectual strength of the heart that “tames” the physical desires (and causes the left side to be physically weaker).
5. The Ohr HaChaim based on the Gemra in Menachos explains that tefillin are supposed to be close to the heart, therefore, we don them on the left arm.
6. The Maharal of Prague similarly explain that we are commanded regarding tefillin, “And these words, which I command you this day, shall be upon your heart.” Since a person’s right hand is stronger, it is more deft, and therefore it’s in constant use and “further away” from the person. So we put the tefillin on the left hand, which is usually kept “closer” to the person.
7. We find many times that Chazal established mitzvos based on the rule of דרכיה דרכי נועם – “the ways of the Torah are pleasant” (see Succah 32 and Yevamos 15). As we mentioned above, the main chiyuv of tefillin is to go around all day with tefillin, and this is how it used to be, they used to go to work wearing tefillin. The Beis Boruch on the Chayei Adam (Klal 14, s.k. 96) writes, that during the times of the Gemara, even a simple shoemaker, or blacksmith would wear tefillin whilst working. When one works he uses his right hand, therefore, to make it easy for people to work, whilst wearing tefillin, Chazal understood that tefillin should be placed on the left hand. (Madanay Asher, in name of R’ Pinchos Rabinovitz and R’ Pinchos Menachen David)
8. The pasuk in Shemos (15:6) says:ימינך ה' נאדרי בכח ימינך ה' תרעץ אויב . Rashi explains that it says the wordימינך twice to teach us, that when Klal Yisroel act the way Hashem wants the left hand becomes a right hand. Perhaps we wear tefillin on the left to remind us in the morning that we should be doing the ratzon of Hashem, and turn our left hand into a right hand.