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I thought that there was a prophet who was particularly opposed to allying with Egypt. Egypt subsequently fell and his position became validated. The Judeans lasted a little longer and then came under control of Assyria or Babylon.

Looking at this now, I can't quite find what I was thinking about. I'm not seeing the overt biblical overture against Egypt that I thought there was immediately prior to Egypt falling. It seems like it would have been during Hezekiah or Josiah.

Hezekiah seems to have allied with the Egyptians, and possibly have been saved by this. During Josiah, I don't see the firm edicts that outlining such a position, or the extent of opposition beyond Megiddo.

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    Using biblical prophets as a sole source puts the question firmly into either JudeoChristian religion or general mythology camps, not History. Is this corroborated by other sources? – jamesqf Jan 13 at 1:46
  • I'll ask on the Christianity.SE meta if this is worth migrating. – KorvinStarmast Jan 13 at 14:11
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There's more than one:

Isaiah (chs. 30-31) criticizes the Israelian and Judean rulers of his time for trying to ally with Egypt against Assyria, and predicts that these efforts will end in failure.

Hosea, a contemporary of Isaiah, also criticizes them for vacillating between Assyria and Egypt (7:11 and 12:2).

Jeremiah (about a century later, when Assyria had been conquered and Babylon was the new northern superpower) speaks of how it's useless to ally with Egypt, how doing so will prove to be fruitless, and specifically that the Egyptian army, on its way to relieving the Babylonian siege of Jerusalem, won't follow through and will return home (2:18,36, and 37:5ff).

Ezekiel (a younger contemporary of Jeremiah) focuses on Zedekiah's perfidy in attempting to ally with Egypt after having sworn allegiance to Nebuchadnezzar of Babylon (ch. 17, particularly v. 15).

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