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Philo reads Genesis 25:23 as God ranking Jacob and Esau while they are still in the womb, because their maker knows his own handiwork before it is finished. Paul quotes the same verse, ranking them before either had acted.
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2500 BCE
1000+ CE

Philo Allegorical Interpretation 3:88

Classical
Once again, of Jacob and Esau, when still in the womb, God declares that the one is a ruler and leader and master, but that Esau is a subject and a slave. For God the Maker of living beings knows well the different pieces of his own handiwork, even before He has thoroughly chiselled and consummated them, and the faculties which they are to display at a later time, in a word their deeds and experiences. And so when Rebecca, the soul that waits on God, goes to inquire of God, He tells her in reply, ‘‘ Two nations are in your womb, and two peoples shall be separated from your belly, and one people shall be above the other people, and the elder shall serve the younger’ (Gen. xxv. 23). For in God’s judgement that which is base and irrational is by nature a slave, but that which is of fine character and endowed with reason and better? is princely and free. And this not only when either is fullgrown in soul, but even if their development is still uncertain. For it is universally the case that even a slight breath of virtue is an evidence not of liberty merely but of leadership and sovereignty, and on the other hand that the most casual beginning of wickedness enslaves the reasoning faculty, even if its offspring have not yet come forth fully developed.
Date: 20-50 C.E. (based on scholarly estimates)

Romans 9:11

New Testament
10 Not only that, but when Rebekah had conceived children by one man, our ancestor Isaac— 11 even before they were born or had done anything good or bad (so that God’s purpose in election would stand, not by works but by his calling)— 12 it was said to her, “The older will serve the younger,” 13 just as it is written: “Jacob I loved, but Esau I hated.”
Date: 55-58 C.E. (based on scholarly estimates)
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Notes and References

#6315
“... Once again, of Jacob and Esau, when still in the womb, God declares that the one is a ruler and leader and master, but that Esau is a subject and a slave. For God the Maker of living beings knoweth well the different pieces of his own handiwork, even before He has thoroughly chiselled and consummated them, and the faculties which they are to display at a later time, in a word their deeds and experiences [...] (3.88-89) But notice that God’s predestination in the case of Jacob and Esau is based on his foreknowledge of their actions and experiences. This raises the question for us of whether this foreknowledge is itself based on God’s creative predetermination of their characters or rather on a divine ability to foreknow free human acts and events. ...”

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