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Sirach lists the ancient giants and the neighbors of Lot as examples of God’s judgment. Jubilees echoes this language and the same pairing, showing that connecting the Watchers to Sodom was a stock warning, already in use when both were written.
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2500 BCE
1000+ CE

Sirach 16:7

Ben Sira, Ecclesiasticus
Deuterocanon
5 Many such things my eye has seen, and my ear has heard things more striking than these. 6 In an assembly of sinners a fire is kindled, and in a disobedient nation wrath blazes up. 7 He did not forgive the ancient giants who revolted in their might. 8 He did not spare the neighbors of Lot, whom he loathed on account of their arrogance. 9 He showed no pity on the doomed nation, on those dispossessed because of their sins;
Date: 195-175 B.C.E. (based on scholarly estimates)

Jubilees 20:5

Pseudepigrapha
4 If any woman or girl among you commits a sexual offense, burn her in fire; they are not to commit sexual offenses by following their eyes and their hearts so that they take wives for themselves from the Canaanite women, because the descendants of Canaan will be uprooted from the earth. 5 He told them about the punishment of the giants and the punishment of Sodom — how they were condemned because of their wickedness; because of the sexual impurity, uncleanness, and corruption among themselves they died in their sexual impurity. 6 ‘Now you keep yourselves from all sexual impurity and uncleanness and from all the contamination of sin so that you do not make our name into a curse, your entire lives into a reason for hissing and all your children into something that is destroyed by the sword. Then you will be accursed like Sodom, and all who remain of you like the people of Gomorrah.
Date: 150-100 B.C.E. (based on scholarly estimates)
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Notes and References

#5903
... 20:5. he told them the judgment of the giants and the judgments of the Sodomites 'Judgment' in both cases is better rendered as 'punishments,' and 'the giants' as 'the Watchers.' God's punishment of the Watchers and the people of Sodom were two famous examples of divine justice. The two are mentioned together in Sirach 16:7-8 and 3 Maccabees 2:4-5. And on account of their fornication and impurity and . . . corruption Compare the three causes of the Flood in Jubilees 7:20. Although Jubilees' author sometimes includes a third term along with fornication and impurity, it is clear that these two are, in his eyes, the main source of Israel's troubles. ...

* 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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