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Sirach echoes the traditions of the Watchers and their giant offspring, a narrative described in detail in the Book of the Watchers in 1 Enoch. Sirach reshapes this tradition and incorporates it into teachings about wisdom and forgiveness.
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2500 BCE
1000+ CE

1 Enoch 13:2

Pseudepigrapha, Apocalypses
1 Enoch went and said: 'Azâzêl, you will have no peace. A severe sentence has gone out against you, to put you in chains. 2 You will not be tolerated, nor will your requests be granted, because of the unrighteousness you have taught, and because of all the godlessness, unrighteousness, and sin you have shown to men.' 3 Then I went and spoke to them all together, and they were all afraid, and fear and trembling seized them. 4 They begged me to write a petition for them so that they might find forgiveness, and to read their petition in the presence of the Lord of heaven.
Date: 300 BCE – 100 CE (based on scholarly estimates)

Sirach 16:7

Ben Sira, Ecclesiasticus
Deuterocanon
5 I have seen many such things with my eyes. My ear has heard mightier things than these. 6 In a congregation of sinners, a fire will be kindled. In a disobedient nation, wrath is kindled. 7 He was not pacified toward the giants of old time, who revolted in their strength. 8 He didn’t spare Lot’s neighbors, whom he abhorred for their pride. 9 He didn’t pity the people of perdition who were taken away in their sins, 10 or in like manner, the six hundred thousand footmen who were gathered together in the hardness of their hearts.
Date: 195–180 BCE (based on scholarly estimates)
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Notes and References

#5244
"... Two observations are in order concerning this litany of God’s judgment on the many. First, ben Sira does not use the stories of Sodom and Gomorrah (fire) and the giants (warfare/flood) as types of a final conflagration. Rather, these two stories take their place among others as example stories. This is a subtle indication that ben Sira’s view of the judgment does not include a catastrophe of cosmic proportions. Second, the statement that God “did not forgive the primeval giants” (אלא נשא לפניכי קדם, Sirach 16:7a) is intriguing. In the Disputation context of Sirach 5:1–8, ben Sira quoted the sinner as presuming that God in his great mercy “will forgive” (סלס, 5:6b) his many sins. Although the verb in Sirach 5:6b is not reused in 16:7a, the two verbs are synonyms and appear together in the present instruction (16:11d). Along with the idea of presuming on forgiveness, there are a number of other parallels between the two contexts that suggest ben Sira is alluding to 5:6 in 16:7. Ben Sira, then, once again offers instruction about the relationship of forgiveness and judgment, but in this instance the instruction is based on the example of the giants of old ..."

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