We have already learned that the mitzvah of brit milah overrides the Sabbath. But what happens when there is a doubt whether a brit milah should be done at all? “The Sages taught in a baraita: The verse states: “And on the eighth day the flesh of his foreskin shall be circumcised” (Leviticus 12:3), and they interpreted the verse: “His foreskin” indicates that only the circumcision of his halakhically certain foreskin overrides Shabbat, and the circumcision of a halakhically uncertain foreskin does not override Shabbat.” (Sefaria.org translation)
The Gemara lists three cases where there is a doubt whether the person needs a brit milah. “(The sages continue from the above citation-gg) and circumcising the foreskin of a hermaphrodite baby, with regard to whom there is uncertainty whether or not circumcision is required, does not override Shabbat. Rabbi Yehuda says: The circumcision of a hermaphrodite overrides Shabbat, and if he is not circumcised, when he reaches majority he is punishable by karet. Rabbi Yehuda interprets the verse in the following manner: His definite foreskin overrides Shabbat; however, the circumcision of one born at twilight does not override Shabbat. And likewise, his definite foreskin overrides Shabbat; however, the circumcision of one who was born circumcised, i.e., without a foreskin, does not override Shabbat. With regard to a child in that condition, there is a dispute between Beit Shammai and Beit Hillel, as Beit Shammai say: It is necessary to drip covenantal blood from him, in lieu of circumcision of the foreskin, and Beit Hillel say: It is not necessary, as he is already circumcised.
“(Rabbi Eliezer has a different tradition concerning the dispute between Bet Shammai and Bet Hillel – gg) Rabbi Shimon ben Elazar said: That was not the subject of their dispute, as Beit Shammai and Beit Hillel did not disagree over the fact that from one who was born circumcised, it is necessary to drip covenantal blood, because they agree that it is a case of a concealed foreskin. The child is not actually circumcised; it is just that his foreskin is not visible. With regard to what did they disagree? With regard to a convert who for some reason was circumcised when he was a gentile and converted when he was already circumcised, as Beit Shammai say: Dripping covenantal blood from him is necessary, and Beit Hillel say: Dripping covenantal blood from him is not necessary, and he needs only a ritual immersion to complete his conversion.” (Sefaria.org translation)
The three cases are: 1, the hermaphrodite who has signs for both male and female genitalia; 2, a baby boy born at twilight. One is not sure whether he was actually born on Shabbat or on Sunday (remember a Jewish day begins the night before); 3, a baby who was born circumcised. The halakhah in all three cases is that the circumcisions do not override the Sabbath. For the hermaphrodite see Shulkhan Arukh, Orekh Hayyim, 331:5; for the child born at twilight see ibid., Yoreh De’ah, 266:8; for the child born circumcised see ibid., ibid., 266:10) There is a fourth case of a premature baby. Back in Talmudic times, a premature baby of eight months was not considered viable. Consequently, because there is a doubt whether the baby will live or not, his brit milah does not override the Shabbat. Nevertheless, later poskim say that this halakhah is no longer practiced because either we know that the baby is viable or that we are not experts in determining whether the baby is one month premature are not. Such a baby’s brit milah does override the Sabbath.
Both a baby who is born circumcised and a
circumcised Gentile man who is joining Jewish people through the process of
conversion need a symbolic ritual to enter the covenant between God and the
Jewish people. A droplet of blood taken from the head of the penis is the sign
of the covenant (hatafat dam brit- הטפת דם ברית). Concerning the convert the Shulkhan Arukh, Yoreh De’ah, 263:4
codifies the necessity of hatafat dam brit. The ceremony also doesn’t override
the Sabbath. After speaking to many of my male adult converts, I’m told that
the ceremony is more frightening than actually painful. The mohel has a special
graded knife that can only nick the surface to allow blood to flow, but does
not permit any harmful damage. The wound heals so quickly that the convert can
enter the mikvah almost immediately.
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