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Numbers 33 warns that the unconquered Canaanites will become thorns in the side of Israel. Paul echoes this language in 2 Corinthians 12, saying a thorn in the flesh was given to him as a messenger of Satan.
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2500 BCE
1000+ CE

Numbers 33:55

Hebrew Bible
54 You must divide the land by lot for an inheritance among your families. To a larger group you must give a larger inheritance, and to a smaller group you must give a smaller inheritance. Everyone’s inheritance must be in the place where his lot falls. You must inherit according to your ancestral tribes. 55 But if you do not drive out the inhabitants of the land before you, then those whom you allow to remain will be irritants in your eyes and thorns in your side, and will cause you trouble in the land where you will be living. 56 And what I intended to do to them I will do to you.’”
Date: 5th Century B.C.E. (Final composition) (based on scholarly estimates)

2 Corinthians 12:7

New Testament
6 For even if I wish to boast, I will not be a fool, for I would be telling the truth, but I refrain from this so that no one may regard me beyond what he sees in me or what he hears from me, 7 even because of the extraordinary character of the revelations. Therefore, so that I would not become arrogant, a thorn in the flesh was given to me, a messenger of Satan to trouble me—so that I would not become arrogant. 8 I asked the Lord three times about this, that it would depart from me.
Date: 55-57 C.E. (based on scholarly estimates)
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Notes and References

#5492
“... 12:7 A: A thorn for the flesh was given to me. skolops = sharp stake, thorn, barb, a metaphorical term for something that causes pain in any way. 1. Numbers 33:55: ‘If you do not drive out the inhabitants of the land before you, what you leave of them will become thorns sikkim (the Septuagint: skolopes) in your eyes and barbs tseninim (the Septuagint: bolides) in your sides, and they will oppress you in the land in which you dwell.’ — The targumim avoided the image. Onkelos: ‘It will happen that those whom you leave will become hordes that will seize weapons against you, and army camps that will encircle you.’ — Yerušalmi I: ‘It will happen that what you leave will become like those who look at you with an envious eye sakhyain (interpretation of sikkim) and will surround you like shields at your sides.’ — Yet ʿArukh knows of a different reading: ‘They will become thorns sikkin in your eyes.’ — Pesiqta 112A: R. Samuel b. Nahman (about 260) opened his presentation with the following, ‘ “If you do not drive out the inhabitants of the land before you” (Numbers 33:55) ...”
Strack, Hermann L., and Paul Billerbeck A Commentary on the New Testament from the Talmud and Midrash, Volume 3: Romans through Revelation (p. 1073) Lexham Press, 2023

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