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Among other places, the following Braisa appears in Eruvin 6b:

לעולם הלכה כבית הלל והרוצה לעשות כדברי בית שמאי עושה כדברי בית הלל עושה מקולי ב"ש ומקולי ב"ה רשע מחומרי ב"ש ומחומרי ב"ה עליו הכתוב אומר (קהלת ב, יד) הכסיל בחשך הולך אלא אי כב"ש כקוליהון וכחומריהון אי כב"ה כקוליהון וכחומריהון

Really, the Halacha follows Beis Hillel. However, one who wishes to hold like Beis Shammai may do so; like Beis Hillel, he may do so; like the leniencies of Beis Shammai and the leniencies of Beis Hillel, he is wicked; like the stringencies of Beis Shammai and Beis Hillel, regarding him the passuk says, “The fool goes in darkness.” Rather, if like Beis Shammai, in their leniencies and their stringencies; if like Beis Hillel, in their leniencies and their stringencies.

In explaining this Braisa, the Gemara (Ibid. 7a) says:

אמר רב שיזבי כי לא עבדינן כחומרי דבי תרי היכא דסתרי אהדדי כגון שדרה וגולגולת דתנן השדרה והגולגולת שחסרו וכמה חסרון בשדרה בש"א שתי חוליות וב"ה אומרים חוליא אחת ובגולגולת בש"א כמלא מקדח וב"ה אומרים כדי שינטל מן החי וימות ואמר רב יהודה אמר שמואל וכן לענין טריפה

Says Rav Sheizbi: When do we not so like two opposing stringencies? When they contradict each other, like the case of the spine and skull, as we taught in a Mishnah:

The spine and the skull that are missing [fragments don’t impart tumah by being in the same room - Rashi]. How much must be missing from the spine [to be subject to this leniency]? Beis Shammai say: two vertebrae. Beis Hillel say: one vertebra. And in the skull? Beis Shammai say: a drill hole. Beis Hillel say: enough that were it taken from a live person, they would die.

And Rav Yehudah said in the name of Shmuel, they likewise argue by treifah. [An animal is only a treifah if it meets these same requirements - Rashi.]

Rashi elaborates:

ומאן דעביד בטריפה כבית הלל וכבית שמאי במת הוי כסיל דהא סתרין עובדי אהדדי דהכא הוי חסרון והכא לא הוי חסרון

One who does by a Treifah like Beis Hillel and like Beis Shammai by a dead person is a fool, for these opinions contradict each other: here this measurement is considered “missing” and here this measurement is considered “missing.”

That is to say: where the reasons of the opinions contradict, we may not hold of two opposing stringencies or leniencies.

Now look at Challah 4:7 (brackets are adapted from Bartenura):

יִשְׂרָאֵל שֶׁהָיוּ אֲרִיסִין לְנָכְרִים בְּסוּרְיָא, רַבִּי אֱלִיעֶזֶר מְחַיֵּב פֵּרוֹתֵיהֶם בַּמַּעַשְׂרוֹת וּבַשְּׁבִיעִית, וְרַבָּן גַּמְלִיאֵל פּוֹטֵר. רַבָּן גַּמְלִיאֵל אוֹמֵר, שְׁתֵּי חַלּוֹת בְּסוּרְיָא. וְרַבִּי אֱלִיעֶזֶר אוֹמֵר, חַלָּה אֶחָת. אָחֲזוּ קֻלּוֹ שֶׁל רַבָּן גַּמְלִיאֵל וְקֻלּוֹ שֶׁל רַבִּי אֱלִיעֶזֶר. חָזְרוּ לִנְהוֹג כְּדִבְרֵי רַבָּן גַּמְלִיאֵל בִּשְׁתֵּי דְרָכִים:

A Jew who sharecrops a non-Jew’s field in Syria: R’ Eliezer obligates its produce in Ma’aser and Shemitah [like Eretz Yisrael], and R’ Gamliel exempts [like outside Eretz Yisrael]. R’ Gamliel requires two Challos in Syria [one to be given to a Kohen and one to be burned, like outside Eretz Yisrael], and R’ Eliezer requires one Challah [like Eretz Yisrael]. They grabbed hold of the leniencies of R’ Gamliel and R’ Eliezer, but then retracted to hold like the words of R’ Gamliel in both cases.

At first, they held of opposing leniencies - contradicting themselves as to whether it was considered Eretz Yisrael or not - and then retracted to hold that it is like Chutz LaAretz in all aspects.

The Bartenura explains that one who holds of opposing leniencies is a wicked person - Tosfos Yom Tov notes that he gets it from the above discussion in Eruvin - and so they retracted to hold like a single authority.

So what were they thinking at first? Did this teaching, that one is wicked for holding of opposing leniencies, suddenly materialize in the middle of this discussion? Why wouldn’t they hold of this teaching originally? Why did they need to retract and they didn’t just hold like one opinion the entire time?

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As you noticed, they indeed changed the halacha to follow Rabban Gamliel in all cases, as Rav Kahati explains.

(עיין בבלי עירובין ו, ב; ז, א) לפי שאין לאחוז שתי קולות הסורות זו את זו

The reason as to why they initially accepted the kulos of both was because the two kulos appeared to be dealing with different areas of halacha. That is, one was speaking about sharecroppers working for gentiles and the halachos of sh'viis and ma'aser. The other halacha deals with a Jew baking bread and having to separate challah. Since this appear to be two completely different areas of halacha, then one can follow the leniencies of both without worrying. However, on further analysis, they realized that the basic reason behind this halacha was whether the halachos of Suriyah were to be compared to those of ארץ ישראל or not. Once this analysis was made, then they wanted to avoid even the appearance of contradiction.

Rav Kahati explains this in his introduction to the mishnah.

כבר ביארנו (דמאי ו, יא; מעשרות ה, ה) שארצות ארם שכבש דוד המלך וסיפחן לארץ ישראל נקראות בתלמוד "סוריה" ואין דינה של סוריה כדין ארץ ישראל לכל דבר, שהואיל ודוד כבש אותה קודם שנכבשה כל ארץ ישראל, לא נתקדש כקדושת הארץ; ואמנם יצאה מכלל חוץ לארץ, אבל לכלל ארץ ישראל לא הגיעה. מכאן, יש דברים שסוריה היא בהם כארץ ישראל, ויש דברים שהיא בהם כחוץ לארץ.

We already explained (Demai 6, 11; Ma'asros 5, 5) that the lands of Aram conquered by David HaMelech and attached to Israel were called in the Talmus "Suriah" and the laws of Suriah are not like the laws of Israel in all matters,Since David conquered it before the entire Land of Israel had been conquered, it did not get the full sactity of the Land; Therefore it left the general category of Chutz La'Aretz, but it did not enter the general category of the Land of Israel. There are matters in which Suriah is like Eretz Yisrael and matters in which it is like chutz La'Aretz.

Originally, those discussing this thought that they could treat each section of the mishnah as an independent halacha and have a different conclusion for each one (the leniencies of both) without a contradiction. However, on further analysis, they realized that both Rav Eliezer and Rabban Gamliel were explaining that the two areas of kedusha were to be considered similar. As a result, the underlying psak as to whether they were to treat Suriah as Eretz Yisrael or Chutz La'aretz had to be the same for these areas. Now that this was concluded, the rule of not following contradicting leniencies applied.

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R. Yitshak ben Malkitsedek of Simponto explains in his commentary to the Mishna there that indeed, originally they followed the leniencies of both, but in the course of time, they learned the teaching that one who follows the leniencies of both is considered bad, and therefore adjusted their practice.

יש לומר על כן חזרו דתניא העושה כבית הלל והרוצה לעשות כבית שמי עושה כקוליהון וכחומריהון, אבל העושה כקולי בית שמי וכקולי בית הלל רשע, כחומרי בית שמי וכחומ' בית הלל עליו הכתוב אומר והכסיל בחשך הולך, ומעיקרא דנהוג לא שמיעא להו ובתר דשמיעא להו הדרי בהו

See also Hazon Ish Shvi'it (4:7) who asks this question ans discusses it.

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  • Rash Mishants and Rosh also give the teaching in Eruvin as the reason why they switched. They does not specify that this was when they learned it.
    – mevaqesh
    Oct 31, 2017 at 20:35
  • The Tifferet Yisrael notes that the hiddush of this Mishna is that the principle in Eruvin even applies to dirabanans. He does not state, however, that this was their mistake before reverting.
    – mevaqesh
    Oct 31, 2017 at 20:39
  • So, indeed, they just didn’t know this teaching before?
    – DonielF
    Oct 31, 2017 at 22:34
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    Yes. He writes this explicitly.
    – mevaqesh
    Oct 31, 2017 at 22:46
  • @DonielF The views of R. Yitshak ben Malkitsedek are particularly noteworthy, since according to Wikipedia, Rash Mishants frequently bases himself off of him. In this case, it therefore seems likely (but definitely not definite) that Rash Mishants, followed Ri ben Malkitsedek, and was in turn followed by Rosh, and Bartenura.
    – mevaqesh
    Nov 3, 2017 at 0:44

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