On Rosh Hashanah the blowing of the shofar resembles our souls crying. The 100 blasts of shofar are like 100 cries. But why 100? We have been taught a strange answer to this question. The 100 shofar cries equate the 100 cries of Sisera's mother. Imagine that! Why should we emulate a woman who was just as evil as her son, the mighty Sisera. She couldn't wait for her son to return with spoils taken from the Jewish People. Sisera was the evil general for Yavin, the king of Canaan, and together they ruled with iron fists. Sisera oppressed the Children of Israel for 20 years. Some say he was the strongest man who ever lived who was able to destroy the walls of major cities with just his mighty voice. There is a special message hidden here for the gematria of Sisera סיסרא is 331, the same as, מאמר הגאולה, "secrets of the redemption."
Devorah, on the other hand, was the good against this evil. She was the only woman to be both a judge and a prophetess. Her influence spread among the Jewish People who repented and returned to G-d. She summoned Barak Ben Avinoam to lead 10,000 men against Sisera. He hesitated from his fear of Sisera but finally agreed to go when Devorah consented to accompany him. He knew that it was only Hashem who determines victory, not the horses, army or chariots. Victory is to the one who fears G-d and follows His ways. Sisera's army was much larger than the one Barak formed, and the intimidation and fear of Sisera spread to Barak's soldiers. But the encouraging words of Devorah gave them strength and then Hashem took over. The Canaanites heard a terrible, loud noise and believed that a tremendous army was coming to attack them, while violent rain and hail bombarded them. By the time Barak's army had appeared, the army of Sisera was fleeing in a panic state. Barak's army killed many, and those that escaped, drowned in a small, tame stream that suddenly turned into a powerful river.
Sisera was really a coward without his men, and fled on foot to the tent of Yael. Poor choice on his part for she was also a judge, extremely brave, who began to make plans for his destruction. Yael, a righteous convert descending from Yisro, knew she couldn't kill him unless he was asleep, so when he asked for a drink, she gave him warm, sour milk to make him sleepy, and then seduced him several times until he fell asleep. Although this was thoroughly against her nature, she did this to save the Jewish People. Since she had no weapons, she took a simple tent pin and drove it into his temple and killed him. And so, the strongest man who ever lived was killed by a woman and a tent pin.
There are numerous similarities between the destruction of Sisera and Pharaoh. Both threatened Israel with powerful armies and chariots, and in both cases, their armies drowned. Both times Hashem fought for the Jewish People and victory came in a miraculous way. Devorah led the people in song just as Moses had done. And in both cases the opposing armies were totally destroyed. The only survivors were Pharaoh, and Sisera. Pharaoh fled when his army was decimated. He was spared so he could tell the world of G-d's greatness. After he was saved, this non-believer said, "Who is like You among the powers, O God?" He went to Nineveh, a major city where he became the king. When Jonah, the prophet, was sent there to warn the people that G-d had taken notice of their evil and was going to destroy them, Pharaoh immediately rose from his throne, tore his garment and dressed in sackcloth and ashes. The people of Nineveh did the same and G-d spared them.
Every person sees the Hand of G-d at some point in their life. But most of us ignore and deny it. We say to ourselves, "what a coincidence that was." But in life, there are no coincidences. Who knows? Maybe Sisera would have also done tshuvah if he survived. Although Sisera did not have the opportunity to do tshuvah, his mother did. There is very interesting language in the part of the Song of Devorah dealing with Sisera's mother. The English translation reads, "at the window, the mother of Sisera looks out and weeps, at the window." The first time window is mentioned, the Hebrew word is החלון, but the second time it's האשׁנב. The different wording seems to indicate that there were 2 different windows. One was a normal window which allowed her to look out and see if her son was coming, and the other window was to look into the future. The Zohar says that this window was used by her for astrology. Some say that it was a magic mirror allowing her to see faraway events. And since the gematria of האשׁנב is 358, the same as Mashiach, it's possible that she could even see our generation, the generation of Mashaich.
When Sisera's mother peered into this window, she saw her son with a woman. She thought that he was up to his old tricks and that's the reason he was delayed. The woman she saw was, of course, Yael. As the hours passed without Sisera returning, her hatred for the Jews increased. In fact, you can rearrange the letters of האשׁנב (magic window), and spell בּשׂנאה (in hatred), to describe her manner towards the Jewish People. But when she looked at the window again, this time, she began to cry. She cried 100 times evidenced by the number of letters in the Book of Judges 5 (28-29), which describes her crying. Something she saw in her special window made her cry. The union between her son and Yael would produce a child. And generations later a descendant from that union, would change the Jewish world forever. A descendant known as Rabbi Akiva. The last 4 words of Devorah's song were added generations later, and the very last 2 words ארבּעים שׁנה (forty years),describe how the land was at rest for 40 years. If you take the gematria of שׁנה which is 355 and add ארבּעים or forty, you get 395, exactly the same gematria or numerical value of Akiva ben Yosef, עקיבה בּן יוסף, the real name of Rabbi Akiva. And it's also interesting to note that it was not until the age of 40 that Rabbi Akiva began to learn and follow the Torah.
Sisera's mother cried when she realized that her son had fathered the ancestor of the "head of all the Jewish sages." Rabbi Akiva, for the first 40 years of his life was an unlearned, enemy of the Rabbis. But at the age of 40, he did tshuvah and while learning, placed himself at the feet of those same Rabbis he previously detested.
The Jewish People would not blow shofar 100 times just because an evil woman cried 100 times for her son. Through our shofars we emulate her crying when she did tshuvah, just like Rabbi Akiva. That's the connection to Rosh Hashanah and shofar blowing. The genuine, tshuvah from someone who was at the lowest point a person can drop to. Can you get any lower than a blatant, anti-Semite? The Jewish People do not need any lessons in crying for our children. Through the pogroms, the holocaust, the suicide bombings etc. we have cried enough tears that could drown all our enemies. But perhaps we need a lesson in genuine tshuvah, that is, repentance that change our lives completely. Major adjustments in our lives that literally create a new person. The Jewish People have a tendency to ask for forgiveness, while knowing deep down inside that they will certainly repeat their errors. Perhaps intensely listening to the crying of the shofar can give us the strength to overcome the temptations of life that the Soton constantly places in front of us. If an evil person like Sisera's mother was rewarded with a Rabbi Akiva for her tshuvah, then imagine how great our reward will be.