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The Question
On a Motza’ei Shabbat when we can recite Kiddush Levanah, do we recite it before or after the Havdalah we recite in the Beit Kenesset?
Havdalah First
On the one hand, Havdalah should be performed first because of the principle of Tadir VeSheino Tadir, Kodem, which states that the activity performed more often should be performed first (Zevachim 89a). This principle has firm Torah roots, as BeMidbar chapter 28 teaches that the Korban Tamid (the daily communal sacrifice) should be offered before the Korban Mussaf (special sacrificial offerings for Shabbat, Rosh Chodesh, and Yamim Tovim). The Torah (BeMidbar 28:23) even states why the Tamid sacrifice is offered before the Mussaf: because we sacrifice the Korban Tamid more frequently (Zevachim 89a).
There are numerous applications of the Tadir principle. Men put on Tallit before Tefillin in part because of this principle (see Beit Yosef Orach Chaim 25 s.v. Veachar). In Kiddush, we recite the Brachah of Borei Pri HaGafen before the Brachah on the Kedushat HaYom in part because of this principle (Pesachim 114a). It is partially because of this principle that we read the portion of Rosh Chodesh before the portion of Chanukah during Kriat HaTorah on Rosh Chodesh Tevet (Tosafot Shabbat 23b s.v. Hadar).
Afukei Yoma Me’Acharinan
On the other hand, Kiddush Levanah should come first since Afukei Yoma Me’Acharinan, we seek to prolong Shabbat. For example, when Yom Tov occurs on Motza’ei Shabbat, we recite Kiddush before Havdalah because of this principle (Pesachim 102b-103a, Rashbam 102b s.v. Rav Amar Yaknah).
Similarly, the Terumat HaDeshen (number 60) rules that Sefirat HaOmer should be recited before Havdalah because of this principle. The Shulchan Aruch (O.C. 489:9) codifies the Terumat HaDeshen, and the Mishnah Berurah does not record a dissenting opinion. The Rama (O.C. 693:1) rules, based on this principle (see Mishnah Berurah 693:3), that we should first read Megillat Esther and only later recite Havdalah. The Mishnah Berurah also does not record dissenting opinions to this ruling. Sepharadim customarily follow this ruling as well (Yalkut Yosef Orach Chaim 693:4).
In these situations, Afukei Yoma Me’Acharinan takes precedence over Tadir. Thus, Kiddush Levanah should be said before Havdalah to delay Shabbat’s end.
The Netziv
The Netziv (Teshuvot Meishiv Davar 2:48), though, limits the Afukei Yoma Me’Acharinan rule to where the two Mitzvot are incumbent upon us simultaneously. For example, the obligations to say Havdalah and to count the Omer or read the Megillah devolve upon us at the same time. In such situations, we say Havdalah second to prolong Shabbat.
However, the Netziv argues that Havdalah should be said before Kiddush Levanah, since one is obligated to say Havdalah in the Beit Kenesset, but obligated to say Kiddush Levanah only when we step outside and see the moon. Thus, he believes we should first discharge the obligation that devolves upon us presently - Havdalah - before addressing a Mitzva for which we are not yet obligated, which is Kiddush Levanah.
Rav Asher Weiss
Rav Asher Weiss (Teshuvot Minchat Asher 1:34) disagrees. He argues that one is obligated to say Kiddush Levanah regardless of whether one sees the moon. Rav Weiss argues that seeing the moon does not trigger the obligation to say Kiddush Levanah, but instead enables fulfilling the requirement to say Kiddush Levanah.
Rav Weiss proves his point from a remarkable ruling of Rav Yechezkel Landau (Teshuvot Noda B’Yehuda 1:41). The Noda B’Yehuda rules that if a community did not yet have the opportunity to recite Kiddush Levanah and the moon became visible on Purim night, the men should go outside the Beit Kenesset and say Kiddush Levanah before reading the Megillah. In this case, the principle of Tadir VeSheino Tadir Kodem applies since Kiddush Levanah is said more often than Megillat Esther. The Chida (Machazik Brachah, Orach Chaim 426, Kuntress Acharon 4, Shaarei Teshuva 426:9 and Sha’arei Ephraim 6:53), Aruch HaShulchan (Orach Chaim 426:9), Kitzur Shulchan Aruch (97:15), and the Kaf HaChaim (426:56) follow Rav Landau’s ruling.
Finally, the Bi’ur Halachah (426:3 s.v. V’Lo) cites the Noda B’Yehuda, citing the portion that discusses if one did not yet say Kiddush Levanah and during Kri’at Shema the moon appeared. If, by the time he finishes Kri’at Shema and the Amida, the time for Kiddush Levanah would elapse, he must interrupt Kri’at Shema and recite Kiddush Levanah. Had the obligation of Kiddush Levanah been triggered only by seeing the moon, the Bi’ur Halachah would not have permitted interrupting Kri’at Shema. Bi’ur Halachah’s citing the Noda B’Yehuda expresses his concurrence.
The Netziv’s approach runs counter to the Noda B’Yehuda’s ruling, as the Netziv would argue that the obligation to read the Megillah applies in the Beit Kenesset, but Kiddush Levanah’s obligation is triggered only after leaving the synagogue and seeing the moon.
Thus, since the Noda B’Yehuda’s ruling is well-accepted, Rav Weiss rules that Kiddush Levanah should be said first.
A Possible Exception – Ein Ma’avarin Al HaMitzvot
Rav Weiss notes a possible exception is if the Havdalah equipment - Yayin, Besamim, and Ner - have already been placed on the Bima. In such a case, the rule of Ein Ma’avarin Al HaMitzvot, which states that we do not pass over Mitzvot (this principle appears throughout Shas, including Pesachim 64b, Yoma 33a–b, 58a, and 70a, Megillah 6b, and Menachot 64b), might apply.
Questioning Rav Weiss’ Ruling
Arguably, Havdalah should be recited first for another reason – Havdalah, according to many Rishonim, is a Torah-level obligation, whereas Kiddush Levanah is unquestionably a rabbinic obligation.
However, the Mishnah Berurah (296:1) teaches that if one has already said Havdalah in Tefilla, the Havdalah on wine is only rabbinic. Moreover, as mentioned, the rule of Afukei Yoma Me’Acharinan applies even to Mikra Megilla, which is not a Torah-level obligation, and to Sefirat HaOmer, which most Rishonim agree is only a rabbinic obligation in the Beit HaMikdash’s absence (Mishnah Berurah 489:14).
Practical Consideration
There is a practical advantage to following Rav Weiss’ ruling. Many people do not remain in the Beit Kenesset for Havdalah since they recite it at home with their families. Delaying Kiddush Levanah until after Havdalah might cause some to not stay for Kiddush Levanah, resulting in a smaller crowd to say Kiddush Levanah, for which we want B’Rov Am Hadrat Melech; a larger crowd to glorify our beloved King.
Conclusion
Some congregations follow Rav Weiss’ ruling. Its compelling, well-founded logic and practical advantages make it a good choice for many Kehilot. Rav Hershel Schachter and Rav Mordechai Willig, though, believe the more common custom is first Havdalah followed by Kiddush Levanah. However, they do not object if it is more practical for a Kehilla to say Kiddush Levanah before Havdalah. Piskei Teshuvot (426:29) similarly concludes that either order is fine.