Introduction - A Surprising Delayed Brit
Everyone at Congregation Shaarei Orah, the Sephardic Congregation of Teaneck, was ecstatic. A first child -- a beautiful little boy -- was born to one of our young couples. We all eagerly awaited the Brit.
The boy, however, suffered from jaundice and the Mohel decided that the Brit could not take place on the eighth day (for further discussion of managing jaundice in regard to Brit Milah, see my Gray Matter 4:163-165). Moreover, the Mohel ruled that a seven day wait was necessary after the boy had recovered from his jaundice. Finally, the seventh day wait was over on a Thursday and the Kehillah expected the Brit to take place that day. However, Sephardic practice calls for a Brit in such circumstances to be delayed to Sunday and everyone wondered why.
Talmudic Background - Shabbat 19a
The Gemara (Shabbat 19a) prohibits embarking on a boat that will travel through Shabbat if the trip begins within three days of Shabbat. However, the Gemara limits this restriction to trips taken for one’s own needs (Devar HaReshut), whereas one may set out for the sake of a Mitzvah even in the latter half of a week. The Shulchan Aruch codifies the Gemara’s rulings (Orach Chaim 248:1). The Steipler Rav (Kehilot Yaakov, Shabbat 14) writes that the Gemara’s prohibition is merely a rabbinic enactment. The Shulchan Aruch Harav (248:7) appears to agree with his view, and Rav Moshe Feinstein (Teshuvot Igrot Moshe, Orach Chaim 1:127) asserts that most authorities indeed consider this prohibition to be rabbinic in nature.
The Rishonim offer a number of explanations for the prohibition against beginning a trip too close to Shabbat. The Rif (Shabbat 7b, in pages of Rif) explains that people generally need three days until they adjust to sea travel. Hence, one who embarks within three days of Shabbat will probably experience an unpleasant Shabbat due to seasickness. The Rabbis thus prohibited such trips in order to ensure that people properly enjoy Shabbat (oneg Shabbat).
The Baal Hama’or (Shabbat 7a, in pages of Rif) claims that the three days immediately before Shabbat are considered “prior to Shabbat,” so one who embarks on a voyage within that period intentionally enters a situation that will require violating Shabbat in case of piku’ach nefesh (saving a life). The Shulchan Aruch (Orach Chaim 248:2 and 248:4) appears to codify both explanations.
Defining “For the Sake of a Mitzvah”
The Gemara permits embarking on a trip during the latter half of a week “for the sake of a Mitzvah.” Rabbeinu Tam (cited approvingly by the Tur, O.C. 248) interprets this concept in an extraordinarily lenient manner. He argues that traveling for business purposes or to visit a friend is considered a Mitzvah, while only a purely recreational trip would constitute a Devar Reshut (trip for one’s own needs). The Rama (248:4) accepts Rabbeinu Tam’s view.
When a Brit Milah (circumcision) takes place later than the eighth day of a boy’s life (such as a baby who could not tolerate a Brit on the eighth day due to health reasons, or a non-Jew who wishes to convert), the Tashbetz (1:21) forbids performing it on a Thursday. He notes that on the third day after a Brit (including the day of the Brit), the baby is presumed to be in tremendous pain (see Bereishit 34:25 and Rashbam ad loc.). Thus, a baby who underwent a Brit Milah on Thursday may require medical treatment that will entail transgressing Shabbat (see Shabbat 86a). The Tashbetz is cited as normative by Rav Yosef Karo in the Bedek HaBayit portion of his commentary to the Tur (Yoreh Deah 262 and 266) and the Taz (Yoreh Deah 262:3). Significantly, Rav Yosef Karo does not cite the Tashbetz in the Shulchan Aruch.
According to the Taz, this problem exists when circumcising on Friday, too, as the baby suffers pain every day through the third day. The Shach (Yoreh Deah 266:18) notes that some Rishonim do indeed assume that the baby suffers through the third day, but the Tashbetz explicitly permits circumcising on Friday even when it is not the eighth day.
The Shach himself rejects even the Tashbetz’s position. He asserts that circumcising constitutes a Mitzvah, so one may perform it even when it will later require violating Shabbat to save a life, just as one may embark on a trip for the sake of a Mitzvah even during the latter half of the week. The Chacham Tzvi (Teshuvot Nosafot 14) and Mishnah Berurah (331:33) rule in accordance with the Shach. The Chacham Tzvi’s son, Rav Yaakov Emden (Sh’eilat Yaavetz 2:95), distinguishes between the late circumcision of a Jewish boy and the circumcision of a non-Jew who wishes to convert. A mitzvah already exists to circumcise the Jewish child, so Rav Emden agrees with the Shach that the brit should not be delayed. By contrast, the potential convert does not delay any mitzvah by pushing off his brit milah, for he is not bound by mitzvot prior to the conversion process.
In defense of the Tashbetz both the Chida (Birkei Yosef Orach Chaim 248) and Chatam Sofer (commentary to Shabbat 137a) argue that the Gemara permits embarking on a trip on a Thursday or Friday only when the opportunity to fulfill the Mitzvah will not be available the following week. However, in a case of Brit Milah it should be delayed until Sunday since the Mitzvah can be fulfilled on Sunday just as well as Thursday or Friday. One could counter, though, that it is improper and possibly prohibited to delay a Brit even when it will not occur on the eighth day of the boy’s life.
Current Practice - Sepharadim and Ashkenazim
In practice, the Magen Avraham (331:9) notes that nowadays we rarely need to violate Shabbat in order to save a circumcised baby, so circumcising on Thursday should undoubtedly be permitted. Indeed, common practice among Ashkenazic Jews is to circumcise on Thursday and Friday under all circumstances, as noted by the Aruch HaShulchan. The Aruch HaShulchan cites the absence of support for the Tashbetz in other Rishonim as evidence for the Shach’s criticism of Tashbetz.
Rav Ovadia Yosef (Teshuvot Yabia Omer, Y.D. 5:23) rules that Sephardic Jews should not perform a belated circumcision on Thursday or Friday unless their community has a custom to do so. Hacham Ovadia writes that we should follow the Tashbetz since it is cited as authoritative by Maran - Rav Yosef Karo - in the Bedek HaBayit, even though it is not presented in the Shulchan Aruch. He cites the custom to follow the Tashbetz ruling from a wide range of Sephardic communities such as Salonika, Turkey, Egypt, Aleppo and Iraq. Moreover, major Sephardic icons such as Maran HaChida (Birkei Yosef Y.D. 262:2), Rav Yosef Chaim of Baghdad (Teshuvot Rav Po’alim 4: Y.D. 28) and Kaf HaChaim (Orach Chaim 331:31) rule in accordance with the Tashbetz. Rav Shmuel Khoshkerman reports that the accepted custom of all Sephardic Jews has emerged to prohibit belated circumcisions on Thursday and Friday. Rav Mordechai Lebhar (Magen Avot Y.D. p.161) confirms that this is the practice of Morrocan Jews as well.
Hacham Ovadia (following the Kaf HaChaim), though, limits his ruling to performing a Milah within two days of Shabbat. He writes that this ruling does not apply to Yom Tov which is not as strict as Shabbat. In addition, he does not believe that it is necessary to postpone to Sunday a Brit for a boy born on Wednesday evening during Bein HaShemashot (the time between sunset and nightfall which is considered both night and day - the Brit is delayed until Thursday is such cases).
The dispute about postponing a delayed Brit from Thursday and Friday to Sunday involves a situation of competing values. On the one hand, is the importance of performing the Brit as soon as possible. On the other hand, we consider the need to preserve the integrity of Shabbat. Ashkenazic practice gives greater weight to performing a Brit as soon as possible and the Sephardic practice accords greater importance to taking precautions to avoid the need to violate Shabbat.
 The Mishnah Berurah (248:4) cites a dispute regarding whether this prohibition applies on Wednesday, or whether the phrase “within three days” includes Shabbat itself as one day.
 The Shulchan Aruch (Orach Chaim 248:4) mentions a trip to Israel as an example of a trip for the sake of a Mitzvah. See Mishnah Berurah 248:28 and Teshuvot Chelkat Yaakov (1:81) regarding whether this includes a temporary visit to Israel.
 Rav Yisrael Rozen (Techumin 16:42) infers this position from the Shulchan Aruch Harav’s words.
 Rav Eliezer Waldenberg (Teshuvot Tzitz Eliezer 12:43:4) cites many authorities who indicate that this prohibition is merely a rabbinic enactment. See, however, B’ikvei Hatzon (p. 153), where Rav Hershel Schachter offers an explanation for why he believes it to be a Biblical prohibition.
 In this chapter, we discuss only the two explanations that appear in the Shulchan Aruch. For a summary and analysis of these and other opinions, see Ritva (Shabbat 19a s.v. Tanu Rabanan).
 Travel was dangerous at that time, so it was likely that the crew would need to perform forbidden activities on Shabbat in order to insure the passengers’ safety.
 Of course, none of these concerns applies when circumcising a baby on the eighth day of his life, as circumcision on the eighth day overrides Shabbat. The Gemara discusses the laws of a circumcision on Shabbat at great length in the nineteenth chapter of Masechet Shabbat.
 The Taz indicates concern for the baby’s pain and suffering per se, not for the desecration of Shabbat that it might necessitate. Apparently, he understands the problem of circumcising close to Shabbat in the same manner that the Rif explains the prohibition against traveling before Shabbat - concern for causing unnecessary discomfort during Shabbat (see Teshuvot Tzitz Eliezer 12:43).
 See, however, Teshuvot Yabia Omer, Y.D. 5:23.