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There is a known rule that Rishonim cannot argue on the Gemara when it comes to "Halachic" drashos. For example, a Rishon will never give a different answer to a question which the Gemara already answered (Tosfos may ask why the Gemara didn't give that other answer, but he will never give his own answer without more). This is true whether the Gemara's subject is practical Halacha or not.

However, when it comes to aggadic drashos on Tanach, we find Rishonim "disagreeing" with Midrashim and late Acharonim disagreeing on Rishonim. Why do Rishonim feel freer to disagree on an explanation of Chumash than to disagree with a Gemara?

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The Rambam writes in one of his letters:

We do not pose difficulties with [i.e. from] the Aggadah. Are they words of Tradition or expressions of reason? Rather each individual considers their explanation as it seems fit to him. In this [Aggadah] there are no words of Tradition, no prohibition and no license, and no law among the Laws; therefore we do not pose difficulties with it. Should you say to me as many have said to me, “Can it be that you apply the term Aggadah [as pertains to this argument] to words of the Talmud?” It is so; all of these words and those similar to them are Aggadah in their reckoning, whether they be written in books of Derashos, whether they be written in books of Aggadah.

This position is echoed by various Ge'onim and Rishonim; see for example Otzar HaGeonim to Chagigah (pp. 59-60) from R. Hai Gaon and R. Shereira Gaon, and the Ramban in his famous Disputation.

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What troubles me with this answer is that the Ramban will knock out Chazal's interpretation in a midrash using logic. If it can be knocked out through logic, why didn't Chazal think of it before choosing that interpretation? –  b a Jun 22 '12 at 20:24
    
@ba Your question refutes itself - because I ask you, based on your own premise, is it possible the rishonim who held this way didn't think of this objection? –  Dov F Jun 22 '12 at 20:30
    
Chazal considered all the problems with an answer (as is evident from the gemara). Saying their reasoning was perfect in halachah but not perfect in agadah is a little inconsistent. But sometimes the truth is inconsistent... –  b a Jun 22 '12 at 20:41
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@ba That's a straw man. Who ever said Chazal's reasoning was perfect in halacha? The fact that we do not veer from the psak of the Gemara does not imply this. –  Dov F Jun 22 '12 at 20:59
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@ba What are you trying to show from Karisos 12a? –  Curiouser Jun 22 '12 at 22:13
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In Dynamics of Dispute, Rabbi Lampel points out that in areas of Aggada, we even find Amoraim breaking the Golden Rule and arguing with Tannaim - see for example Megillah 7a in which Shmuel claims he has a better source for the Divine nature of Megillas Ester:

אמר שמואל אי הואי התם הוה אמינא מלתא דעדיפא מכולהו שנאמר קימו וקבלו קימו למעלה מה שקיבלו למטה אמר רבא לכולהו אית להו פירכא לבר מדשמואל דלית ליה פירכא

Said Shmuel: Had I been there, I would have said something better than everything they [the Tannaim] said, as it says etc... Said Rava: All of them [the answers of the Tannaim] have a weakness, but Shmuel's answer does not have a weakness

Rabbi Lampel has a thesis which he uses this to support, namely that the reason in general that Amoraim do not argue with Tannaim is because there was a chain of tradition regarding which halachos were Halacha L'Moshe MiSinai (he proves this with other methods as well), and that chain of tradition was lost in the mayhem of the generation of Rabbi Yehuda HaNasi. Therefore the Amoraim would not argue for fear of inadvertently arguing with a Halacha L'Moshe MiSinai. However, in Aggada there is no such concern, and therefore they felt free to argue. (He also concludes from this thesis that if a given Halacha is clearly not from Sinai, for example if a Tanna had an opinion but then changed his mind about it, then an Amora was free to argue on that Halacha as well, and he cites examples of such.)

This would justify arguing with essentially any authority in an Aggadic discussion.

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Sh'muel does not argue with tanaim (there). He says "were I there, I'd argue" -- but then he'd be a tana. –  msh210 Feb 28 at 18:13
    
@msh210 I didn't translate it, but he offers his own opinion. It's like saying "I'm not going to tell you that you're ugly" - it doesn't become that I didn't say it by saying I won't say it. Shmuel said a different opinion not stated by Tannaim. And Rava concluded it was the most solid opinion. This is how R' Lampel takes the Gemara. I personally think the "If I were there" bit is to state that they would have agreed with him. –  YEZ Feb 28 at 18:22
    
"אי הואי התם הוה אמינא" sounds like "לולא דמסתפינא" to me, but I don't know. +1, anyway. –  msh210 Feb 28 at 18:24
    
We find him arguing in Halachic Drashas also (end of Yoma regarding the source that Safek Pikuach nefesh doche Shabbos) –  Shmuel Brin Mar 26 at 22:28
    
@ShmuelBrin arguing about the source of a drasha but supporting the same halacha would further conform to this - as long as you don't risk unintentionally arguing with a halacha l'Moshe mi'Sinai, it's fair game to argue with Tannaim. Especially if the source is explicitly given as not a HL"M –  YEZ Mar 26 at 22:39
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