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It seems like the Bais Hillel had a tendency to be lenient in Halachic matters vs the Bais Shammai, it was a sort of a presumption to them in which they were almost always successful to back up with their methods of Derash (and the same goes for Bais Shammai regarding their stringency). Was it a principle the Bais Hillel believed in (perhaps it was based on "Deruchehu Darchei Noam")? or was it some kind of train of thought? We find the same pattern in the later Achronim. For example: R moshe Feinstein vs. Chazon Ish...

  • related judaism.stackexchange.com/q/38526/759 – Double AA Apr 26 '17 at 20:54
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    The Chazon Ish was indeed significantly more Meikil than R Feinstein about Eruvin, one of the most practically important weekly issues to many Jews. – Double AA Apr 26 '17 at 20:55
  • Related: judaism.stackexchange.com/q/48478/5323 – Shokhet Apr 27 '17 at 1:12
  • I think this was an inherent part of their personalities. Avot Derav Nattan cites many examples of their behavior. One notable sample is when someone challenged another to try to anger Hillel. He couldn't do it despite asking Hillel 3 "crazy" questions. Shamai was much more easily irked by people. Another sample is that Shamai believed that only great minds can become great scholars. Hillel believe that we should teach everybody. – DanF Apr 27 '17 at 15:16
  • I have 9/10 of an answer at judaism.stackexchange.com/a/67462/1570 . All one needs to be added is that students who confuse the role of the nasi with an overall approach to Torah are going to be more humanistic in their pesaqim than those who confuse the role of av beis din with an overall approach. – Micha Berger Apr 28 '17 at 0:22
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This is touched on in the sefer Kovetz Yesodos V'Chakiros in the ״לשיטתם-ביאור מחלוקות״ section, which attempts to codify and find consistencies in arguments among the both the Bavli and Yerushalmi or other personalities of Shas.

The sefer, basing itself on Sifrei Kabbalah and Chassidus (בספר לאור ההלכה ״לשיטות בית שמאי וב״ה) characterizes the methodologies of both Beis Shammai and Beis Hillel in the following way:

  1. Beis Hillel judges cases according to the מציאות - the reality, therefore they judge with the midda of Chesed. This naturally leads to being more lenient.

  2. Beis Shammai judges cases according to theory (i.e. Non practical), they judge using the midda of Din, which is more strict.

The author attempts to prove this suggestion from a plethora or sources, too numerous to recount here.

  • I was looking for a more practical and rational answer. – Bach Apr 27 '17 at 18:26
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    @Bach perhaps you should actually make that clear in your question, rather than let people put in the time and effort to fruitlessly answer your question. Thanks – Shoel U'Meishiv Apr 27 '17 at 18:27
  • I'm sorry you feel that way. You did a great job, just not my style :( – Bach Apr 27 '17 at 18:28
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    @Bach welcome to the site. Please forgive my terse tone, please do not confuse it for being annoyed. – Shoel U'Meishiv Apr 27 '17 at 18:38
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    The plethora would be too numerous, but with no examples at al this answer is very abstract and hard to understand. Reality=chesed and theory=din? Huh? Says who? What does that even mean? Adding one example that helped you understand the position presented would add value to this answer. – Baby Seal Apr 30 '17 at 6:04

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