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Sirach and Wisdom of Solomon both draw on traditions about the Watchers and their giant offspring from 1 Enoch. Sirach treats their destruction as past history and Wisdom expands this idea, saying their fall allowed hope for a new generation.
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2500 BCE
1000+ CE

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,
Date: 195–180 BCE (based on scholarly estimates)

Wisdom of Solomon 14:6

Deuterocanon
4 showing that you can save out of every danger, that even a man without skill may put to sea. 5 It is your will that the works of your wisdom should not be ineffective. Therefore men also entrust their lives to a little piece of wood, and passing through the surge on a raft come safely to land. 6 For in the old time also, when proud giants were perishing, the hope of the world, taking refuge on a raft, left to the world a seed of generations, guided by your hand. 7 For blessed is wood through which comes righteousness; 8 but the idol made with hands is accursed, itself and he that made it; because his was the working, and the corruptible thing was called a god.
Date: 50 BCE – 50 CE (based on scholarly estimates)
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Notes and References

#2428
"... The corrupting consequences of Adam’s transgression in Wisdom of Solomon 2:23–24 are not irreparable for the cosmos, for Adam, or for his progeny ... Adam is set in contrast to the prototypical transgressor in Wisdom, Cain (Wisdom of Solomon 10:3–4) ... Adamic tradition occurs in the context of condemning idolatry (Wisdom of Solomon 15:8–17). Like Cain, the idolater forfeits his soul through his folly ... like Sirach 16:7, Pseudo-Solomon makes passing reference to the Enochic tradition (Wisdom of Solomon 14:6). In Wisdom of Solomon 2:23–24 Adam’s transgression is, for the first time, attributed profound significance. However, in the larger context of Wisdom, Adam’s transgression does not deny or overshadow other traditions related to the origin of evil. Like Ben Sira, the author of Wisdom testifies to a diverse collection of traditions related to evil, a mixed template ..."
Tyler Allen Stewart, “‘The Present Evil Age’: The Origin and Persistence of Evil in Galatians” (diss., Marquette University, 2019), 106–107.

* 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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