Havdalah - Talmudic Sources

(6) If [those at the table] are sitting upright, each one blesses for himself. If they are reclining, one blesses for them all. If wine came during the meal, each one says a blessing for himself. If after the meal, one blesses for them all. The same one says [the blessing] over the incense, even though the incense is not brought until after the meal.

There are conflicting opinions with regard to reciting havdala over the cup of wine after reciting it in the Amida prayer. One opinion holds that it is appropriate to recite havdala a second time, while the other holds that it is prohibited. Ravina said to Rava: What is the halakha? Rava said to him: The halakha in the case of havdala is like the halakha in the case of kiddush. Just as in the case of kiddush, although one recited kiddush in the Amida prayer he must, nevertheless, recite kiddush again over the cup of wine, so too with havdala, although one recited havdala in the Amida prayer he must recite havdala again over the cup of wine...

...MISHNA: This mishna speaks of additions to the standard formula of the Amida prayer and the blessings in which they are incorporated. One mentions the might of the rains and recites: He makes the wind blow and the rain fall, in the second blessing of the Amida prayer, the blessing of the revival of the dead. And the request for rain: And grant dew and rain as a blessing, in the ninth blessing of the Amida prayer, the blessing of the years. And the prayer of distinction [havdala], between the holy and the profane recited in the evening prayer following Shabbat and festivals, in the fourth blessing of the Amida prayer: Who graciously grants knowledge. Rabbi Akiva says: Havdala is recited as an independent fourth blessing. Rabbi Eliezer says that it is recited in the seventeenth blessing of the Amida prayer, the blessing of thanksgiving.

GEMARA:

...We learned in the mishna that havdala, distinguishing between Shabbat and the weekdays, is added in the blessing of: Who graciously grants knowledge. Here too the Gemara asks: What is the reason that havdala is recited specifically in that blessing? Rav Yosef said: Havdala is recited in that blessing because it requires wisdom to distinguish between two entities, they established it in the blessing of wisdom. The Rabbis say a different reason: Because havdala is the distinction between the sacred and the profane, the Sages established it in the blessing of weekdays. The first three blessings of the Amida prayer are recited both on weekdays and on Shabbat and Festivals. The blessing: Who graciously grants knowledge, is the first of the blessings recited exclusively during the week.

...A tannaitic dispute is cited in the mishna with regard to the appropriate blessing in which to recite havdala within the Amida prayer. Rabbi Akiva says: Havdala is recited as an independent fourth blessing. Rabbi Eliezer says that it is recited in the seventeenth blessing of the Amida prayer, the blessing of thanksgiving.

The first tanna says that it is recited in the fourth blessing of the Amida prayer: Who graciously grants knowledge. Regarding this, Rav Shemen, Shimon, bar Abba said to Rabbi Yoḥanan: Now, since the eighteen blessings of the Amida prayer and the other prayer formulas for prayer were instituted for Israel by the members of the Great Assembly just like all the other blessings and prayers, sanctifications and havdalot; let us see where in the Amida prayer the members of the Great Assembly instituted to recite havdala. Rabbi Yoḥanan replied that that would be impossible, as the customs associated with havdala went through several stages. He said to him: Initially, during the difficult, early years of the Second Temple, they established that havdala is to be recited in the Amida prayer. Subsequently, when the people became wealthy, they established that havdala is to be recited over the cup of wine. When the people became impoverished, they again established that it was to be recited in the Amida prayer. And they said: One who recites havdala in the Amida prayer must, if he is able (Shitta Mekubbetzet, Me’iri), recite havdala over the cup of wine as well. Due to all these changes, it was not clear when exactly havdala was to be recited.

It was also stated: Rabbi Ḥiyya bar Abba said that Rabbi Yoḥanan said: The members of the Great Assembly established for Israel blessings and prayers, sanctifications and havdalot. Initially, they established that havdala is to be recited in the Amida prayer. Subsequently, when the people became wealthy, they established that havdala is to be recited over the cup of wine. When the people again became impoverished, they established that it was to be recited in the Amida prayer. And they said: One who recites havdala in the Amida prayer must recite havdala over the cup of wine as well. It was also stated: Rabba and Rav Yosef who both said: One who recites havdala in the Amida prayer must recite havdala over the cup of wine as well.

Rava said: We raise an objection to our halakha based on what was taught in a Tosefta: One who erred and did not mention the might of the rains in the second blessing in the Amida, the blessing on the revival of the dead, and one who erred and failed to recite the request for rain in the ninth blessing of the Amida, the blessing of the years, we require him to return to the beginning of the prayer and repeat it. However, one who erred and failed to recite havdala in the blessing: Who graciously grants knowledge, we do not require him to return to the beginning of the prayer and repeat it, as he can recite havdala over the cup of wine. Apparently, havdala over the cup of wine is optional, not obligatory, at it says because he can recite and not that he must. The Gemara answers: Do not say as it appears in the Tosefta: Because he can recite havdala over the cup of wine. Rather, say: Because he recites havdala over the cup of wine. Proof that one must recite havdala over the cup of wine as well as in the Amida prayer.

It was also stated: Rabbi Binyamin bar Yefet said that Rabbi Yosei asked Rabbi Yoḥanan in Sidon, and some say that Rabbi Shimon ben Ya’akov from the city of Tyre asked Rabbi Yoḥanan, and I, Binyamin bar Yefet, heard: One who already recited havdala in the Amida prayer, must he recite havdala over the cup of wine or not? And Rabbi Yoḥanan said to him: He must recite havdala over the cup.

Having clarified the question whether one who recited havdala during the Amida prayer must also recite havdala over the cup of wine, a dilemma was raised before the Sages: One who already recited havdala over the cup of wine, what is the ruling as far as his obligation to recite havdala in the Amida prayer is concerned? Rav Naḥman bar Yitzḥak said: This can be derived a fortiori from the established halakha regarding havdala in the Amida prayer. Just as havdala in the Amida prayer, which is where the principal ordinance to recite havdala was instituted, the Sages said that it is not sufficient and one who recited havdala in the Amida prayer must recite havdala over the cup of wine as well, all the more so that one who recited havdala over the cup of wine, which is not where the principal ordinance to recite havdala was instituted, but was merely a later addition, did not fulfill his obligation and must recite havdala in the Amida prayer.

Rabbi Aḥa Arikha, the tall, taught a baraita before Rav Ḥinnana: One who recited havdala in the Amida prayer is more praiseworthy than one who recites it over the cup of wine, and if he recited havdala in this, the Amida prayer, and that, over the cup of wine, may blessings rest upon his head.

This baraita is apparently self-contradictory. On the one hand, you said that one who recites havdala in the Amida prayer is more praiseworthy than one who recites havdala over the cup of wine, indicating that reciting havdala in the Amida prayer alone is sufficient. And then it is taught: If one recited havdala in this, the Amida prayer, and that, over the cup of wine, may blessings rest upon his head. And since he fulfilled his obligation to recite havdala with one, he is exempt, and the additional recitation of havdala over the cup of wine is an unnecessary blessing. And Rav, and some say Reish Lakish, and still others say Rabbi Yoḥanan and Reish Lakish both said: Anyone who recites an unnecessary blessing violates the biblical prohibition: “Do not take the name of the Lord your God in vain” (Exodus 20:7).

Rather, emend this baraita and say as follows: If one recited havdala in this and not in that, may blessings rest upon his head. Rav Ḥisda asked Rav Sheshet with regard to these blessings: If one erred in havdala both in this and in that, what is the ruling? Rav Sheshet said to him: One who erred in this, the Amida prayer, and that, over the cup of wine, returns to the beginning of both the Amida prayer and the havdala over the cup of wine.