by: Rabbi Yechezkel Khayyat
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The Gemora discusses the parameters of what may be on one’s head at the same time as tefillin. The Gemora cited three statements:
1. A braisa that states that if one has a burden on his head, which presses down on the tefillin, it is prohibited. The braisa clarifies that a burden of four kavs or more is prohibited. (This is the measure which the Beis Medrash of Rabbi Yannai referred to.)
2. Rabbi Chiya’s braisa, which said that if one is carrying refuse on his head, he must remove the tefillin and keep them respectfully on his arm.
3. Rabbi Shila’s students said that even the bag of the tefillin may not be placed on the head. Abaye explains that this is very light.
Rabbi Chiya’s statement need not contradict either statement, since Rabbi Chiya was limited to a case of refuse, which is qualitatively a disgrace to place next to tefillin, regardless of the burden’s size.
However, at first glance, Rabbi Shila’s position is at odds with the first braisa. In fact, the Rambam (Tefillin 4:23) rules like Rabbi Shila, permitting nothing aside from a usual head covering.
The Gr”a explains that the Rambam allowed normal head coverings, since the Gemora refers to Dovid Hamelech wearing a crown together with tefillin (Avoda Zara 44a), and the Kohen Gadol wearing the mitznefes together with the tefillin (Zevachim 14a-b).
However, the Rif (Brachos 14b) and the Rosh (Brachos 3:31) cite all three statements, without ruling like any one in particular.
To explain this position, the Rishonim and Acharonim suggest various distinctions between the statements to reconcile the seeming contradiction:
1. Rabbi Shila is stating that optimally one should not place anything on his head with tefillin, while the braisa is stating that if one placed the burden on, he may leave it there unless it is four kavs or heavier. [Bais Yosef (OH 41) in the name of Mahari Abuhav]
2. The braisa is referring to one who is carrying a load for his work, and therefore is more lenient. [Bais Yosef in the name of Mahari Abuhav]
3. The braisa is referring to one who is first carrying the burden, and then wants to put on tefillin, while Rabbi Shila is referring to one who is first wearing tefillin, and wants to place the burden on his head. When the burden was there first, it need not be removed unless it is four kavs or heavier. [Bais Yosef]
4. The braisa is referring to a burden that is on one’s head, but not on the tefillin. Since a burden of four kavs is likely to be heavy enough to crush tefillin, the Sages prohibited one from putting such a burden on his head. Rabbi Shila is referring to a burden on the tefillin itself, which is prohibited at any size. [Bais Yosef]
5. Rabbi Shila is referring to a burden not usually placed on the head, which is never allowed, since it is a disgrace to the tefillin. The braisa is referring to a normal head covering (e.g., hat), which is only prohibited when it is heavy enough to crush the tefillin. [Rama] (See MB 41:4, who rules that one should not place a hat on the tefillin if it rests heavily on it).
6. Rabbi Shila is referring to someone wearing tefillin at home, who has no need to put anything on his head, while the braisa is referring to someone outside who is transporting the burden. [Aruch Hashulchan]
See Taz and Prisha for more details.