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Both Yovel and Shavuos are the fiftieth after a cycle of 7 sets of 7 (7 Shmittas, each 7 years/ 7 weeks each 7 days) and both are after “Shabbos” - we start counting the Omer “after Shabbos”, so Shavuos is also “after Shabbos”/ Shmittah is called Shabbos, and Yovel is the year after the seventh Shmittah, so it is also “after Shabbos".

Do any of our sources discuss this connection?

Al Berko
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Lo ani
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    https://www.yutorah.org/lectures/lecture.cfm/924359/rabbi-jonathan-ziring/yovel-and-shavuot/ – Double AA May 17 '19 at 11:32
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    Chazal say that only one who learns Torah is truly free, and they derive it from the Luchos. Nice comparison to Yovel, where the slaves and property goes free and returns to its original owner. That said, a contrast can be drawn in this regard as the former is חרות and the latter דרור. – DonielF Jun 05 '19 at 23:51
  • see https://judaism.stackexchange.com/a/104556/5083 – הנער הזה Jun 06 '19 at 20:43
  • ואלין חמשין מ"ט וכו': ואלו חמשים יום, מ"ט יום הם כלל הפנים של התורה. כי יש בתורה מ"ט פנים טהור. כי ביום החמשים הוא סוד התורה ממש. ואלו הם חמשים יום שבהם שמיטה ויובל, ז' שמיטות ויובל אחד. ואם תאמר, איך יש כאן חמשים, והלא מ"ט הם, שאין אנו סופרים יום החמשים. ומשיב. אחד, הוא נסתר, והעולם נסמך עליו, וביום החמשים ההוא, בשבועות, מתגלה הנסתר ומתכסה בו. כמלך הבא לבית ידידו, ונמצא שם. אף כאן כך הוא יום החמשים וכבר העמדנו סוד הזה. https://www.sefaria.org.il/Sulam_on_Zohar%2C_Emor.177.1?lang=he&with=all&lang2=he – The GRAPKE Nov 19 '23 at 14:55
  • @TheGRAPKE I personally don't understand what he's saying. If you can explain it, then please do! – Lo ani Nov 20 '23 at 01:31
  • There are 49 facets to the Torah. This means that the 50th aspect of the Torah is the inner hidden aspect of the Torah which all other 49 facets reveal when understood in unison. Shavuos corresponds to this hidden 50th aspect of the Torah. The shmittah and yovel cycle are a cycle of finding Hashem, each year corresponds to one of the preparation days for Matan Torah. On yovel man is able to find the hidden aspect of himself and of Hashem which corresponds to the hidden inner true aspect of the Torah that was revealed on Shavuos. – The GRAPKE Nov 20 '23 at 07:44

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Sure, there's the 7x7 levels, middot, space-time -- but then there's the Fiftieth gate that's way beyond all that, the Nun, Binah, Ima Ilaah etc. See the Tikkunei Zohar and I'm sure these are mentioned in the many discussions of 7*7 and 50 in that sefer, which is very short and easy btw. So both the Jubilee and Shavuot share in that aspect.

I think you see this same Fifty in the Haggadah while Chokhmah is Yud, 10, so you see those numbers many times there.

Edit. Found this in the TZ it contains 2 of the only 3 mentions of Yovel in the sefer and the first one not quoted here equates Ima Ilaah with the Yovel. Here you have a discussion of Yetziat Mitzrayyim (i.e. Shavuot - it doesn't say that but hey what isn't Y"M, Shabbat and all YT are all זכר ליציאת וכו' ) and Yovel, you can check it..

תיקוני זהר דף עו/ב

זמנין אשר הוצאתיך מארץ מצרים, אמר ליה רבי שמעון הכי הוא ודאי, אבל הכא לא משבח קודשא בריך הוא גרמיה דאפיק לון מן גלותא, אלא חמשין זמנין אדכיר באורייתא יציאת מצרים, לאשתמודעא בדרגא דאפיק לון דאיהו יובלא, דאתמר ביה יובל היא שנת החמשים שנה, ואינון חמשין תרעין דבינה דאתמסרו למשה מסיני בר חד דלא אתמסר ליה, ובגין דא אדכיר חמשין זמנין באורייתא יציאת מצרים. אמר הא ודאי אתישב דעתאי: ...

Nissim Nanach
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  • Thanks! But I'm looking for a source that specifically connects shavuos and yovel, if possible (and not just the fact that 49/ 50 means something, which can then be said about both yovel and shavuos). – Lo ani Nov 23 '23 at 21:20
  • Also, I don't fully understand your comment about the Haggada... – Lo ani Nov 23 '23 at 21:21
  • @Loani Mitzrayyim were struck 10 times says R Abba, R Eleazar says five times 10 .. or something like that. Yud, 10, is Chochmah and Binah, Nun==50. You'll see this many times in the Zohar and the rest of the Sefarim. – Nissim Nanach Nov 26 '23 at 18:30