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I teach a gemara shiur to older folks, with a focus on skill-building (understanding the structure and logic behind the gemara).

I find that sometimes -- to give a little peek at how the Torah is so much deeper than we realize, and also for a little variety -- it's been helpful to drop in a little bit of concepts from chassidus and kabbalah that may be hinted at in the text.

For example, mentioning that the Arba Avos Nezikin (four main categories of damage) correspond to four character defects, which are rooted in the four elements.

Or explaining, just as the Avos (Patriarchs) represented different middos (character traits), so too, the Tanaim and Amoriam (sages in the Mishna and Talmud). This explains, for example, why Beis Hillel is always lenient (they're Chessed, "Kindness," which is expansion) and why Beis Shammai is always strict (they're Gevurah, "Strength/Justice," which is constriction.)

I've picked up a few concepts over the years, but not a whole lot. Do you know of any Jewish books that systematically go through the Gemara with commentary of this nature?

(I'm looking for something that sheds a different light on the HALACHIC parts of the gemara, NOT for aggada.)

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  • Do you have an article I can read about the 4 nezikin idea you mentioned May 23, 2023 at 19:37
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    @CuriousYid The 4 nezikin idea is elaborated upon by the Gra in his commentary on Agadata (Bava Kamma): hebrewbooks.org/pdfpager.aspx?req=14226&st=&pgnum=90 May 23, 2023 at 22:18
  • While not on the gemara per se, the Likutei Halachos by R' Noson miNemerov has deep kabbalistic insights into halachah/mitzvos. You can probably use it alongside a gemara to great effect.
    – Yehuda
    Jan 11 at 17:44

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Bi'urei HaChassidus on Shas, by Rabbi "Yishai" (Yisrael Yitzchak) Chassidah

Published by Mossad Harav Kook

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You might find Torat Menachem Hadranim al HaRambam v'Shas by the Lubavitcher Rebbe to be exactly what you are looking for.

Enjoy!

Although not exactly what you are looking for, if you haven't looked at the Me'loh HaRo'im by Rabbi Yaacov Tzvi Yolles of Dinov, you might this extremely helpful. And he is a kabbalistic and Chassidic Master of the highest order.

Me'loh HaRo'im volume 1

Me'loh HaRo'im volume 2

Me'lh HaRo'im volume 3

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  • Great source Yaakov. Do you know if this sefer also covers perek cheilek in Sanhedrin? Did the Rebbe ever wrote something on it?
    – Shmuel
    May 23, 2023 at 18:37
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    @Shmuel If you are specifically focusing on Perek Chelek, my suggestion would be to look at any of the Rebbe's ma'amarim that that begin with the words, כל ישראל יש להם חלק לעולם הבא. There are many. You might also find the Chiddushim of the Tzemach Tzedek helpful. hebrewbooks.org/… May 23, 2023 at 18:52
  • Thanks! I might turn this into a question later on.
    – Shmuel
    May 23, 2023 at 18:57
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    Rabbi Yaacov Tzvi Yolles of Dinov, was a kabbalistic and Chassidic Master of the highest order, but I don't think that his "Me'loh HaRo'im" is relevant to the discussion at all. May 23, 2023 at 22:21
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Here are some resources I know about that are a little bit helpful, but not really what I'm looking for:

  1. Divrei Yisrael (Modgitz sefer). Has alphabetical index in back with concepts. But only some are halachic concepts from the gemara explained in a chassidic way, and I could use something arranged by the pages of gemara, not alphebetical.

  2. Daf al HaDaf. Has tons of commentary and it's arranged according to the pages of gemara. But only a little bit of it is the kind of insights I'm looking for. (There are 21 volumes, most of them available as a free download from Hebrewbooks [dot] org.

  3. Margaliyos haShas. Goes according to pages of gemara, lots of insights. However, only some is the kind I'm looking for, and it's only on several mesechtas.

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I found two more sefarim that fit what I'm looking for:

  1. Pi Hatzaddik al haShas - Tzaddok hakohen.

  2. Sefer Galgal haChaim -- goes through the aggadas in shas and explains them in light of who the people were in previous gilgulim.

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