In response to a reader's comment to my post about my son's Upsherin, I wanted to post some selected translations from Rav Gavriel Zinner's sefer Nitei Gavriel on Upsherin and Chinuch.
(Page 17) The custom to cut a boy's hair for the first time is mentioned in the Responsa of the Radvaz (Rav David ibn Zimra, mid-1500s) (2:608), regarding one who vowed to cut his son's hair at the [grave] of Shmuel Hanavi, only to find that the place had already been taken by the gentiles... and Jews were not allowed to enter there...Rav Zinner also says in the text of perek 1, halacha 1 that the main purpose of the Upsherin is to begin the child's education by teaching him the isur, the prohibition of "Lo sakifu p'as rosheichem," "do not round the corners of your heads."
[From this source, it appears that] it was the custom to cut the hair of the boys for the first time by the grave of Shmuel haNavi, and to dedicate silver, equivalent to the weight of the hair, for the purpose of lighting the grave of Shmuel, and to give the rest to the congregation and to tzedaka.
(Page 31, note 2) And so too in the Sefer Mat'amim Erech Sa'aros V'Otzar Minhagei Yeshurun, that the reason for the custom that we don't cut the hair of a little boy until he begins to speak is because it is written in the Gemara in Sukkah 42a, that a child, when he begins to speak, his father should teach him Torah. And what is Torah? "Torah Tziva Lanu Moshe, etc." Thereby, he sanctifies him to Heaven. And it is written (Devarim 18:4), The first shearing of your flock shall you give to me." and the Jewish people are called [Hashem's] flock. And therefore, when the child begins to speak, and we bring him into holiness, we his hair from him, and give its [weight's] monitary value to Heaven. And then, we also educate him to Mitzvos and leave for him Peyos, and make him a Jew, so that it will be recognizable to all that this child is a Jew."
Here are a few guidlines I heard from my rebbe about the ideal ways to do an Upsherin, whenever possible, and if Shalom Bayis can be maintained:
-Have a small Upsherin, preferably with just the parents and the Rav, or at least with as few people as possible. The smaller, the better.
-Have as few people as possible cut the hair. And preferably, the people who cut his hair should be Shomer Shabbos men.
-A gentile should not be his first barber.
-The first spot where the hair should be cut is in the place of the Tefillin, as a preperation for that mitzva later in life by getting rid of the excess hair there, which would be a chatzitza, a barrier to the Tefillin.
-Both parents should say the short tefillah before the Upsherin that's in the back of the Nitei Gavriel.
(Video is of a Biala Upsherin)
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