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Death and Mourning in Jewish Text and Tradition: Class #3 - Aninut, Kriyah, Kaddish
ואלא עלמא אמאי קא מקיים אקדושה דסידרא ואיהא שמיה רבא דאגדתא שנא' (איוב י, כב) ארץ עפתה כמו אופל צלמות ולא סדרים הא יש סדרים תופיע מאופל
The Gemara poses a question: But if everything is deteriorating, why does the world continue to exist? The Gemara answers: By the sanctification that is said in the order of prayers, after the passage that begins: And a redeemer shall come to Israel, which includes the recitation and translation of the sanctification said by the angels, and by the response: Let God's great name be blessed, etc., which is recited after the study of aggada. As it is stated: “A land of thick darkness, as darkness itself; a land of the shadow of death, without any order” (Job 10:22). Therefore, it can be inferred from this verse that if there are orders of prayer and study, the land shall appear from amidst the darkness.
Machzor Vitry,
11th-century prayer book by Rabbi Simcha of Vitry, a French scholar & disciple of Rashi.

A tale of Rabbi Akiva: he was walking in a cemetery by the side of the road and encounter in there a naked man, black as coal, carrying a large burden of wood on his head. He seemed to be alive and was running under the load like a horse. Rabbi Akiva ordered him to stop. “How come you are doing such hard work? If you are a servant and your master is doing this to you then I'll redeem you from him. If you're poor then I'll give you money.” “Please, sir,” that man replied, “do not prevent me, because my superiors who will be angry.” “Who are you? Rabbi Akiva asked, “and what have you done?” The man said, “the man whom you're addressing is a dead man. Every day they send me out to chop wood and they use it to burn me up.” Rabbi Akiva said to him: “My son, what was your work in the world from which you came?” “I was a tax collector and a leader of the people, I showed favor to the rich and killed the poor, and more, I transgressed many serious trangressions.” He said to him: “Have you heard nothing from your superiors about how you may relieve your condition?” “Please, sir, do not detain me, for you will irritate my tormentors. For such a man as I, there can be no relief. Though I did hear them said something – but no, it is impossible. They said that if this poor man had a son, and his son were to stand before the congregation and recite the prayer ‘Bless the Lord who is to be blessed’ and the congregation were to answer ‘amen’, and his son were also to say the kaddish and they answer ‘May God's great name be blessed’, they would release him from his punishment. But this man does not know if he had a son. He left his wife pregnant and he did not know whether the child was a boy, and even if she gave birth to a boy, who would teach the boy Torah? For this man does not have a friend in the world.”

Immediately Rabbi Akiva took upon himself the task of discovering whether this man had fathered a son, so that he might teach the son Torah, and install him at the head of the congregation to lead prayers. “What is your name?” he asked. “Akiva,” the man answered. “And what is the name of your wife?” Shoshniva.” “And the name of your town?” “Lodkyia.”

Rabbi Akiva was deeply troubled by all this and went to make his inquiries. When he came to that town, he asked about the man he had met, and the townspeople replied: “May his bones be ground to dust!” He asked about the man's wife, and he was told: “May her memory be erased around the world!” He asked about the man's son. Rabbi Akiva promptly took him and sat him down [to teach him]. But the boy refused to receive Torah. Rabbi Akiva fasted for 40 days. Then a heavenly voice was heard to say: “For these you mortify yourself?” “But Lord of the universe,” Rabbi Akiva replied, “it is for You that I am preparing him!” Suddenly the Holy One Blessed Be opened the boy's heart. Rabbi Akiva thaught him Torah and the reading of the Shema, the 18 blessings, and the benediction after meals. He presented the boy to the congregation and the boy recited the prayer ‘Bless the Lord who to be blessed’ and they answered ‘May the great name be blessed’. And he said the kaddish, and they answered "May God'st great name be blessed'. And after that he taught him mishnah and Talmud, laws and aggadot, until he got very wise, and he is Rabi Nachum HaPakuli, - and how many sages came from him!)

At that very minute the man in the cemetary was released from his punishment. The man immediately came to Rabbi Akiva in a dream, and said: “May it be the will of the Lord that your soul find delight in the Garden of Eden, for you would have saved me from the sentence of Gehenna. When you made my son enter the house of gathering/synagogue, and he said the kaddish, my terrible sentence was ripped up. And when you made him enter the house of study, all my judgments were cancelled. And when he became wise and was called 'my teacher' my seat was put in Gan Eden with the righteous and pious ones, and they crowned me with many crowns. And all this was through your merit”. Rabbi Akiva opened his discourse with: “Your name, oh Lord, endures forever, and the memory of You through the generations!” (Ps. 135:13) For this reason it became customary in the evening prayers on the night after Shabbat are led by a man who does not have a father or a mother, so that he say can say Kaddish and say “Bless the Lord who is to be blessed.”
הגה: וכשהבן מתפלל ומקדש ברבים פודה אביו ואמו מן הגיהנם
The ReMA's gloss explaining Askenazi minhag: And when the son prays and sanctifies (says Kaddish) in public, he redeems his father and mother from Geihenom.
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