Q: Why is failing to wear Tefillin such a severe
transgression that the Gemara (Rosh Hashanah 17a) says: "Who are the
sinners of Israel? Rav said: a skull that
did not wear Tefillin"? Can someone
who did not put on Tefillin rectify their sin?
A: Some explain that "a skull that did not wear
Tefillin" refers to someone who did not wear Tefillin even one time during
his lifetime (Rabbenu Chananel ibid. and Rif ibid. 4a). Others explain that the reason he never put
on Tefillin is because the Mitzvah is embarrassing to him. He does not want to put straps and boxes
around his head and on his arms (Tosafot ibid. and Rosh ibid. 1:5). And there are still others who explain that
this statement does not only apply to Tefillin but to any mitzvah that is done with
one's body, since it is forbidden to shame any mitzvah and it is a disgrace not
to fulfill it even one time (Ron ibid. in pages of the Rif and Korban Netanel
ibid. #10). The Tosafot there, however,
did mention that if someone did not put on Tefillin, he is able to repent. Everything can be repaired. Nothing stands in the way of repentance even
in the case of severe transgressions.
The Tosafot said that if he repents, the repentance will hang in the
balance until he dies and the suffering of death will complete the process of
repentance. There are people who stand
in the street and try to get Jews to put on Tefillin even if they will not do
so again. The last Lubavitcher Rebbe –
Ha-Rav Menachem Mendel Schneerson – explained that a person should put on
Tefillin at least once in his lifetime so he does not have "a skull that
did not wear Tefillin" according to the first explanation (see Sha'arei
Halachah U-Minhag vol. 1, p. 84).
