Exploring the opinion of R' Yehuda, the Gemara works out many possibilities with the Cohen Gadol marrying a second wife and simultaneously "divorcing her with a condition" retroactively. Why couldn't the Cohen Gadol "marry his second wife with a condition", prospectively?
(That is, if his first wife dies, then the marriage takes effect. If his first wife continues living, nothing occurs.)
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1) MAKING A "KIDUSHIN" THAT WILL TAKE EFFECT ON YOM KIPUR
QUESTION: The Torah requires that the Kohen Gadol be married when he performs the Avodah on Yom Kipur (Vayikra 16:11). Furthermore, he may only be married to one woman, and not to two (ibid.). If the Kohen Gadol is not married, he may not perform the Avodah. Because of these requirements, Rebbi Yehudah maintains that, prior to Yom Kipur, another wife was arranged for the Kohen Gadol in order to ensure that he remains married in case his first wife dies on Yom Kipur. However, he could not simply marry another woman, because he may not be married to two wives when he performs the Avodah.
The Gemara proposes a complex arrangement whereby the Kohen Gadol marries a second woman before Yom Kipur and then divorces both wives conditionally, in such a way that at any given moment during Yom Kipur, he has one wife and not two, yet he is assured that if one dies he will still be married. The conditions are made such that if one of the two women dies then that woman will be divorced retroactively (from before Yom Kipur) so that he was not be married to two women when he begins the Avodah. If both women live, then the second wife will automatically be divorced retroactively.
There seems to be a much simpler solution that the Gemara could have offered to ensure that the Kohen Gadol remain married. The Kohen Gadol should simply marry a woman (that is, do Kidushin (Erusin) and Nisu'in (Chupah)) on Yom Kipur at the moment that his first wife dies!
Alternatively, if it is argued that it is not possible to marry a woman on Yom Kipur because of the Halachah (Beitzah 36b) that one may not be Mekadesh a woman on Yom Tov, then let him be Mekadesh her before Yom Kipur on condition that if his present wife does on Yom Kipur, the Kidushin of the second one will take effect at the moment that the first one dies. Why did the Gemara not offer this solution? (SHA'AGAS ARYEH #93)
(a) TOSFOS (13b, DH v'Chada) cites a Yerushalmi that says that indeed, the Kohen Gadol marries a second wife on Yom Kipur if his first wife dies. Even though marrying a woman on Yom Tov is forbidden because of Shevus, the principle of "Ein Shevus b'Mikdash" (the prohibitions of Shevus do not apply in the Beis ha'Mikdash) permits it.
However, the Bavli clearly does not accept this, seemingly because this type of Shevus is not permitted even in the Mikdash ("Shevus d'Medinah Lo Hutar ba'Mikdash," Eruvin 103a). However, why does the Bavli not allow the Kohen Gadol to be Mekadesh the second wife before Yom Kipur with a condition that it take effect on Yom Kipur, as we asked? (In fact, according to our Girsa in the Yerushalmi, this is actually what the Yerushalmi suggests.)
(b) REBBI AKIVA EIGER (Teshuvos I:159) and the SI'ACH YITZCHAK discuss whether a person is allowed to make an act of Kinyan prior to Shabbos which will take effect on Shabbos. They prove from our Sugya that it is considered a Shevus and is prohibited, because if it was permitted, then the Gemara should have said that the Kohen Gadol should make a Kidushin with a second wife on condition that it takes effect on Yom Kipur when the first wife dies, as the Sha'agas Aryeh suggested. Since the Gemara does not say this, it must be that it is prohibited because of Shevus.
However, Rebbi Akiva Eiger adduces proof that it is permitted from the TERUMAS HA'DESHEN (cited by the Magen Avraham OC 339:8) who implies that it should be permitted to perform a Pidyon ha'Ben on Shabbos even though the money cannot be given on Shabbos. The father may give the money to the Kohen before Shabbos and say that he wants the Pidyon to take effect on Shabbos. (The Terumas ha'Deshen concludes that the only reason this is not done is because it will not be possible to recite the blessings neither on Shabbos nor on Erev Shabbos.) We see that the Terumas ha'Deshen assumes that it is permitted to do an act of Kinyan (and similarly, Kidushin) which will take effect on Shabbos.
(c) TOSFOS understands from the Yerushalmi that the act of bringing a wife into the Chupah (the Nisu'in) is also a Shevus, like the Kidushin. Accordingly, perhaps the reason why one may not make a Kidushin on condition that it take effect on Yom Kipur is because even though the Kidushin itself can take effect later, the Chupah will have to be done on Yom Kipur, and that is prohibited because of Shevus.
The Chupah cannot be done prior to Yom Kipur on condition that it take effect on Yom Kipur, because the act of Chupah cannot take effect at a later time. Unlike the money given to consummate a Kinyan or a Kidushin, which will be extant the next day, an act that is transitory and will no longer be extant the next day cannot take effect the next day. (REBBI AKIVA EIGER (ibid.), though, appears to assume that a Chupah can take effect on the following day.)
The RI HA'LAVAN suggests that the act of Chupah cannot be done on Yom Kipur for a different reason. Even if it is not a Shevus, there is another problem. There is no way to make a Chupah -- it cannot be done with Bi'ah because Bi'ah is forbidden on Yom Kipur; a normal walk-under Chupah cannot be done on Yom Kipur because the Kohen Gadol must remain sequestered and cannot leave the Azarah. (Similarly, the new wife cannot come to join him there for a Chupah, either because it would be a breach of his Perishah, or because of the ruling of Rashi (Kidushin 52b DH v'Chi) and the Tosefta (Erchin 2:1) that prohibit women from entering the Azarah when not bringing a Korban.)
Rebbi Akiva Eiger adds that a Chupah cannot be performed at this point for an additional reason. The Gemara (Kesuvos 56a) discusses whether a Chupah which is not fit to be consummated with Bi'ah is a valid Chupah or not. The RAMBAM (Hilchos Ishus 10:2) rules that it is not a valid Chupah. Thus, a Chupah done on Yom Kipur is not valid since Bi'ah is forbidden on Yom Kipur, and the Chupah is not fit for Bi'ah. Even according to those who do not rule Halachically like the Rambam, and prohibit such a Chupah, our Gemara might be trying to avoid the issue of making such a Chupah because of the doubt cast on it in Kesuvos.
(d) The RITVA says that even if it is permitted to do the act of Chupah on Yom Kipur, there is still a concern that his wife will die while he is in the middle of an Avodah and he will not be able to interrupt to marry another wife, and make a Chupah, at that moment. (Chupah cannot be done through a Shaliach.)
(See also what we wrote at the end of the following Insight.)