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On Rosh Hashana, per a widely accepted custom, we blow the shofar one hundred times. This custom is based on Masechta Rosh Hashanah 33B which says that the phrase below, in the song of Devora, which uses the word "yebava", describes the sound of Shofar being blown. This phrase described how Sisra’s mother sat by a window and awaited his return from the pillage and destruction of the Jews.
( Shoftim 5:28-30)
כח בְּעַד הַחַלּוֹן נִשְׁקְפָה וַתְּיַבֵּב אֵם סִיסְרָא, בְּעַד הָאֶשְׁנָב: מַדּוּעַ, בֹּשֵׁשׁ רִכְבּוֹ {ר} לָבוֹא-- מַדּוּעַ אֶחֱרוּ פַּעֲמֵי מַרְכְּבוֹתָיו.
"Through the window peered Sisera's mother; behind the lattice she cried out (tiyabev), 'Why is his chariot so long in coming? Why is the clatter of his chariots delayed?' Her wise ladies answered her, yea, she returned answer to herself, "They're really finding and dividing the loot: A girl or two for each soldier, colorful clothes for Sisera, colorful, embroidered clothes, and two pieces of colorful, embroidered cloth for the neck of the looter."
It seems then that the 100 blows on the shofar are based on the 100 cries of Sisera's mother when her son does not return from battle against the Jews (Tosafos in Rosh Hashana 33b). The derivation of a holy act of Shofar blowing on one of the holiest days of the Jewish calendar from the wailing of a mother of an evil and depraved man, who mourns that he has been prevented from his wanton acts of destruction and piracy is striking. Many mefarshim have difficulty accepting such a negative role model.
Rabbi Brander gives Rabbi JB Soloveitchik's answer after saying that this analogy is tantamount to saying that Osama bin Laden, Arafat, or Hitler (rub out their names)'s mother is the basis for minhag Israel. One can say that this connection is purely linguistic and has no deeper significance. See also here.
Some other sources:
http://www.mail-archive.com/daf-discuss@shemayisrael.co.il/msg00169.html as well as shaky, non-frum sources http://www.shalomctr.org/node/465 .
None resolve the difficulty and are quite contrived. In Chabad, Likutei Levi Yitzhak (Shemos- Devarim p.42), it is simply stated that Sisera's mother is from the negative side of Klipah.
However see Megale Amukos who brings down that Rebbe Akiva descended from Sisera. The descendants of Sisera, according to Gittin 57b, were teachers of the young in Jerusalem. Sisera is crying because her descendent R. Akiva is still so far in the future.
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Commentary by Avakesh
I am indebted to Dr. Gershon for initiating the discussion between us.
First, a few more explanations of the connection to Sisera.
The MESHECH CHOCHMAH (Parshas Tazria) cites Vayikra Raba 27:7, which says that when a woman gives birth, she wails and cries out one hundred times. 99 of those cries are out of the conviction that she is going to die, and the final, 100'th cry is out of the realization that she is going to live after all. Similarly, we blow one hundred Teki'os on Rosh Hashanah. 99 are blown out of our fear of the judgment of the day, but with the one- hundredth we demonstrate our confidence that we will emerge from our judgment blessed with life.
ArtScroll brings from Sefer Hatodaah that the lesson for us is that even in our triumph, our exaltation in victory should be tempered by compassion for a mother who just lost her son, even though both the mother and the son were truly evil.
Now to the commentary. According to the Yalḳuṭ Shimoni on Judges 4:3, Sisera hitherto had conquered every country against which he had fought. His voice was so strong that, when he called loudly, the most solid wall would shake and the wildest animal would fall dead. Devorah was the only one who could withstand his voice and whom it did not cause to stir from her place. Underlying this midrash is the constrast between the name of Devorah, which is her speech to the "voice" of Sisera. The name Devorah literally names speech and this prophetess is first introduced to us as the one who speaks to Barak to prod him into action and then as one who speaks "a song". The Shofar is also a form of wordless speech. The voice of Shofar can express what words cannot.
The Biblical narrative itself juxtaposes Devora and Yael. Sisera's mother completes the triumvirate of mothers. The name of Yael has something to do with elevation. Both women opposed Sisera but in very different ways. Devorah led the army that battled Sisera, while Yael submitted to him in order to smash his “head", that is, his power, and from his lower regions and his weakness she produced R. Akiva and 40 years of peace.
There is more to say here for Devora is also a “mother in Israel” (5:7) and then there is Sisera’s mother longing for her son (5:28). But this is for another time.
According to the same source in Yalkut, thirty-one kings followed Sisera merely for the opportunity of drinking the waters of Israel . Undoubtedly, although this was the real motivation of these kings, they were not aware of it. If asked, they would have answered, "We are going to fight the Jews". Here one finds that expression of the idea that the true inner motivation of what appears to be evil acts can be to draw closer to Holiness.
Megale Amukos can be interpreted as teaching this important lesson. A superficial observer would think the Sisera's mother cried for her depraved son and was conforted with the assurance that he was surely delayed because he was engaged in pillage, robbery and rape. However, in the depths of her psyche and soul, whe was crying and pining for R. Akiva who was destined to come from Sisera, and therefore also from her.
“It should be known that that just as powers of holiness are sustained through the Light of King’s Countenance so do the powers of impurity derive their vitality from the same source. When the Presence is revealed, all draw toward it…. When the effusion of spirituality overtakes them and they are not suitable for it, they are harmed. This is why the firstborns in Egypt (and their gods) were destroyed (as Hashem went forth in the midst of Egypt). (Netsiv, Commentary to Exodus 11, 3).
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