(I presented a version of these divrei Torah [took out personal references and some other stuff] at the shloshim siyum for my FIL, Dovid ben haChaveir Yosef. They should be an aliya for his neshoma)
The gemara (Pesachim 68) writes that Shavuos was Rav Yosef’s favorite holiday:
רב יוסף ביומא דעצרתא אמר עבדי לי עגלא תלתא אמר אי לא האי יומא דקא גרים כמה יוסף איכא בשוקא
We all would be nothing without mattan Torah. What did Rav Yosef have more of an appreciation and make a greater celebration of the day than anyone else’s? And if Rav Yosef was celebrating mattan Torah, why does he not say “mattan Torah?” Why does the gemara refer to “hai yoma,” the day?
The gemara at the end of Horiyos tells us that Rav Yosef was called “Sinai” because he had an unbelievable memory and could recall braisos as if they had been dictated to him word for word from Sinai.
However, at some point Rav Yosef's condition changed (Nedarim 41):
רב יוסף חלש איעקר ליה למודיה אהדריה אביי קמיה היינו דבכל דוכתא אמרינן אמר רב יוסף לא שמיע לי הדא שמעתא א"ל אביי את אמריתה ניהלן ומהא מתניתא אמריתה ניהלן
Rav Yosef forgot his learning. This is why throughout shas we find Abayei reminding his rebbe, Rav Yosef, of sugyos that Rav Yosef had taught him but had now forgotten.
In light of Rav Yosef’s condition, we can appreciate his comment (Menachos 99a)
אשר שברת ושמתם בארון תני רב יוסף מלמד שהלוחות ושברי לוחות מונחין בארון מכאן לתלמיד חכם ששכח תלמודו מחמת אונסו שאין נוהגין בו מנהג בזיון
Rav Yosef himself was the shivrei luchos! He proved that even after he could no longer function on the level he once was able to, his life still had meaning, and his life could still be lived with dignity and respect. Broken luchos can be cherished as much as whole ones.
Rav Yosef celebrated not just the giving of the luchos, mattan Torah, like we all do, but he in particular celebrated the fact that Torah was given through shivrei luchos, through that would be broken, and that even these luchos too would have a place in the aron.
A second reason why the Shavuos had particular meaning for Rav Yosef:
The gemara (Kid 30a) writes that someone who teaches Torah to his grandchildren is as if he received it directly at Har Sinai, like at Shavuos.
אמר ריב"ל כל המלמד את בן בנו תורה מעלה עליו הכתוב כאילו קבלה מהר סיני שנאמר והודעתם לבניך ולבני בניך וסמיך ליה יום אשר עמדת לפני ה' אלהיך בחורב
This idea of ensuring that Torah is passed down to children, and grandchildren as well, is reflected in another statement of Chazal (B”M 85):
ר' יוחנן כל שהוא תלמיד חכם ובנו תלמיד חכם ובן בנו תלמיד חכם שוב אין תורה פוסקת מזרעו לעולם שנאמר ואני זאת בריתי וגו' לא ימושו מפיך ומפי זרעך ומפי זרע זרעך אמר ה' מעתה ועד עולם מאי אמר ה' אמר הקב"ה אני ערב לך בדבר זה מאי מעתה ועד עולם אמר ר' ירמיה מכאן ואילך תורה מחזרת על אכסניא שלה
Rav Yochanan said it, but Rav Yosef lived it. The gemara continues:
רב יוסף יתיב ארבעין תעניתא ואקריוהו לא ימושו מפיך יתיב ארבעים תעניתא אחריני ואקריוהו לא ימושו מפיך ומפי זרעך יתיב מאה תעניתא אחריני אתא ואקריוהו לא ימושו מפיך ומפי זרעך ומפי זרע זרעך אמר מכאן ואילך לא צריכנא תורה מחזרת על אכסניא שלה
(Parenthetically, why does the gemara say that R”Y fasted 40 days for himself, 40 for his children, but 100 [others change the girsa, but this is how the printed text reads and how Maharasha has it] for his grandchildren? I am admittedly a newbie in the role of grandparent, but it seems to me that by the time one’s children are grown and one gets to be a grandparent, one realizes that however many tefilos, fasts, etc. one thought would be enough to ensure the mesorah continues to the next generation, in reality even twice as much is not even enough.)
Rav Yosef’s life was Shavuos, was mattan Torah, because he established that bond across generations. That's why the day had such special meaning for him.
Shavuos is the time we are judged on “peiros ha’ilan.” It's a time to take stock of one's efforts to pass the mesorah on to the fruits of one’s family tree, children and grandchildren. Hopefully the effort bears spiritual fruit.
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