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In 1 Enoch, Michael trembles with pity at the fallen angels’ sentence yet will not plead for them. This echoes Greek myth, where Aeschylus describes the same reluctant executioner in Hephaestus, who pities the bound Prometheus but is overruled by Zeus.
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2500 BCE
1000+ CE

Aeschylus Prometheus Bound

Classical
KRATOS: We've now journeyed to a remote part of the earth—the Scythian wilderness, an untrodden wasteland. Now, Hephaestus, you must carry out the task our father assigned: shackle this wrongdoer to the jagged rocks with unbreakable, adamantine chains. He stole your precious fire, the source of all forging, and gave it to mortals—a grave offense for which the gods demand justice. Let him learn to endure Zeus's rule and stop his favoritism toward humans. HEPHAESTUS: Kratos and Bia, Zeus's command is fulfilled for you; you have nothing more to do. But to forcibly bind a fellow god in chains in this stormy abyss—I lack the courage. Yet I must find strength from necessity, for woe to anyone who disobeys the Father's word. Noble son of wise counsel, with a heavy heart, I must burden you with these brass bonds, difficult to undo, nailing you to this cliff where no one lives, where no human voice or figure will visit you. The sun's blaze will scorch your flesh; your fair skin will change. Night will be welcome when it hides the light of day; the returning sun will disperse the morning frost. Every hour will bring new pain to wear you down; for the one who will free you hasn't been born yet. This is your reward for loving humanity. Being a god, you defied the gods' anger, preferring humans over divine honor. Therefore, your vigil on this rock will be joyless, never able to close an eye or bend a knee. Your cries and laments will be in vain, for Zeus is hard to persuade; new power is always merciless. KRATOS: Enough! Why hesitate? Why waste pity? Isn't the god whom the gods hate also hateful to you? A traitor to the gods and to your own status? HEPHAESTUS: Kinship and friendship are heavy burdens.
Date: 479 B.C.E. (based on scholarly estimates)

1 Enoch 68:3

Pseudepigrapha
2 On that day, Michael said to Raphael, 'The power of the spirit overwhelms me and makes me tremble because of the severity of the judgment of the secrets, the judgment of the angels: who can withstand the harsh judgment that has been meted out, which causes them to dissolve?' 3 Michael spoke again, saying to Raphael, 'Who can remain unaffected by this judgment, whose heart is not softened and whose resolve is not shaken by this decree that has been issued against them because of their misleading ways?' 4 As he stood before the Lord of Spirits, Michael said to Raphael, 'I will not support them in the presence of the Lord, for the Lord of Spirits is displeased with them because they act as though they were the Lord. Therefore, all that is hidden shall befall them for eternity; for neither angel nor man shall share in their fate, but they alone will bear their judgment forever and ever.'
Date: 200-50 B.C.E. (based on scholarly estimates)
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Notes and References

#6123
... Perhaps it not only reflected elements in the Parables but also imitated something like 1 Enoch 9-10, where the four archangels discuss, and then intercede for, the victimized inhabitants of the earth, and where they execute judgment against the fallen angels and their progeny. Here we catch a glimpse of a discussion about intercession in behalf of the fallen angels. See also 1 Enoch 13:4-7, where Enoch actually performs this task. The point of the 'dialogue' here is that it is not worth even attempting such intercession. There is also an interesting parallel between this narrative fragment and the opening scene in Aeschylus's Prometheus Bound (lines 1-54). Out of pity, Hephaestus hesitates to chain Prometheus to the rock, but Kratos finally persuades him that the wrath of Zeus is implacable. ...
Nickelsburg, George W. E. A Commentary on the Book of 1 Enoch Chapters 37-82 (p. 293) Fortress Press, 2012

* The use of references are not endorsements of their contents. Please read the entirety of the provided reference(s) to understand the author's full intentions regarding the use of these texts.

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