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At the end of the curses for disobedience in Deuteronomy 28, verse 68 says:

And the Lord will bring you back in ships to Egypt, a journey that I promised that you should never make again; and there you shall offer yourselves for sale to your enemies as male and female slaves, but there will be no buyer." (ESV)

What is meant by being brought "back in ships to Egypt"? Did this happen historically?

Also, how can God warn Israel with making a journey "[he] promised that [they] should never make again"?

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...I am the Lord, and I will bring you out from under the burdens of the Egyptians, and I will deliver you from their bondage, and I will redeem you with an outstretched arm, and with great judgments; and I will take you to Me for a people, and I will be to you a God; and ye shall know that I am the Lord your God, who brought you out from under the burdens of the Egyptians. And I will bring you in unto the land, concerning which I lifted up My hand to give it to Abraham, to Isaac, and to Jacob; and I will give it you for a heritage: I am the Lord. (Exodus 6:6-8, JPS)

God makes it very clear to the children of Israel that the objective of the exodus is the subsequent arrival in the land of Israel. The exodus from Egypt is not merely a liberation from slavery, but a means of attaining the land of Israel and the fulfillment of historical destiny. The most tragic and severely punished event in the entire Torah, found in Numbers 13, is when Moses' spies return from exploring the land of Israel and say that they prefer Egypt. Throughout the Tanakh, Egypt and Israel are set up as two opposing and mutually exclusive ideological/cultural paradigms.

If we adhere to God's word, we will be protected from the afflictions that God placed on Egypt:

and said, "If thou wilt diligently hearken to the voice of the LORD thy God, and wilt do that which is right in His sight, and wilt give ear to His commandments and keep all His statutes, I will put none of these diseases upon thee which I have brought upon the Egyptians; for I am the LORD that healeth thee." (Exodus 15:26, KJV)

And by the same token, all the afflictions that God placed on Egypt are given as a punishment for disobedience:

Moreover He will bring upon thee all the diseases of Egypt which thou wast afraid of, and they shall cleave unto thee. (Deut. 28:60, KJV)

The return to Egypt described in Deuteronomy 28:68, “a journey which I promised you should never make,” describes the exile from the land of Israel as an undermining and reversal of the entire exodus process.

This prophecy was fulfilled when the Babylonian empire exiled the people of Israel and destroyed the First Temple. It's a matter of tragic irony that this prophecy of doom would not be directly fulfilled by the Babylonians, but by the frieghtened people of Israel who leave on their own accord:

"Thus saith the LORD, the God of Israel, unto whom ye sent me to present your supplication before Him:  'If ye will still abide in this land [the land of Israel], then will I build you and not pull you down, and I will plant you and not pluck you up; for I repent of the evil that I have done unto you.  Be not afraid of the king of Babylon, of whom ye are afraid; be not afraid of him, saith the LORD, for I am with you to save you and to deliver you from his hand. And I will show mercies unto you, that he may have mercy upon you and cause you to return to your own land.'  "But if ye say, 'We will not dwell in this land,' neither obey the voice of the LORD your God, saying, 'No, but we will go into the land of Egypt where we shall see no war, nor hear the sound of the trumpet, nor have hunger for bread, and there will we dwell'--  and now therefore hear the word of the LORD, ye remnant of Judah! Thus saith the LORD of hosts, the God of Israel: 'If ye wholly set your faces to enter into Egypt, and go to sojourn there,  then it shall come to pass that the sword which ye feared shall overtake you there in the land of Egypt, and the famine whereof ye were afraid shall follow close after you there in Egypt; and there ye shall die.  So shall it be with all the men that set their faces to go into Egypt to sojourn there. They shall die by the sword, by the famine, and by the pestilence; and none of them shall remain or escape from the evil that I will bring upon them.'

(Jeremiah 42:9-17, KJV)

...then spoke Azariah the son of Hoshaiah, and Johanan the son of Kareah, and all the proud men, saying unto Jeremiah, "Thou speakest falsely. The LORD our God hath not sent thee to say, 'Go not into Egypt to sojourn there.' But Baruch the son of Neriah setteth thee against us, to deliver us into the hand of the Chaldeans, that they might put us to death and carry us away captives into Babylon." So Johanan the son of Kareah, and all the captains of the forces, and all the people obeyed not the voice of the LORD to dwell in the land of Judah. But Johanan the son of Kareah and all the captains of the forces took all the remnant of Judah, who had returned from all nations whither they had been driven, to dwell in the land of Judah-- even men, and women, and children, and the king's daughters, and every person whom Nebuzaradan the captain of the guard had left with Gedaliah the son of Ahikam, the son of Shaphan, and Jeremiah the prophet, and Baruch the son of Neriah. So they came into the land of Egypt, for they obeyed not the voice of the LORD; thus came they even to Tahpanhes.

(Jeremiah 43:2-7 KJV)

It's worth reading Jeremiah 42 and 43 in full since these are awesome chapters.

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    +1: But what about the "ships"? Nov 8, 2011 at 23:55
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    @JonEricson, a) Today and in Biblical times people travel from Israel to Egypt by sea, b) I don't think that the only time the threat in Deut. 28 was ever carried out was in Jeremiah 43. I assume that over the course of multiple exiles there were plenty of opportunities for Israelites to be put on ships and sold as slaves in Egypt-whether or not we have a record of it.
    – Amichai
    Nov 9, 2011 at 0:28
  • Drop the vowels, Ships also means sorrow, and they have the root 'I'. So he is saying, "Though at times you wished to return to Egypt, in this case I myself will take you back to Egypt in sorrow."
    – Bob Jones
    Jul 6, 2012 at 1:18
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    @BobJones, that would be a great answer from a text-critical point of view! Could you write it up with an example of which Hebrew word for "sorrow" you intend here?
    – Frank Luke
    Apr 4, 2013 at 14:23
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    Other than the initial vowel point, both Hebrew words are identical (H591 = אֳנִיָּה = ship) and (H592 = אֲנִיָּה = mourning), although it would seem odd, since the latter word otherwise only appears twice in the Hebrew Bible as part of the expression "lamenting and mourning" (Is 29:2 & Lam 2:5). If it is H592 then one fulfillment would be Josephus Wars of the Jews, Bk 6, Ch. 8 §384: the Romans find the Jews are worth little to nothing as slaves, and the young males were deported to Egypt to work as slaves in the Egyptian mines (Ch. 9 §418). There is no mention of "ships" of course.
    – Joseph
    Apr 4, 2013 at 18:37
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Using the reference at hand: JPS Torah Commentary on Deut, page 273, note on the verse:

Mekelburg and some modern commentators suggest reading ho-`oniyyot as "in mourning, in a lamentful condition." They understand `oniyyot as `anniyyot, an abstract plural of `anniyah, 'mourning, lamenting'.

The footnote, in turn, reads:

Meklenburg; NEB; Mayes: cf. NJPS at Is 43:14. This interpretation requires revocalizing ho-`oniyyot to ha-`aniyyot. For the singular see Isa 29:2; Lam 2:5; for the abstract form see GKC section 124d-f; B.K. Waltke and M. O'Connor, Biblical Hebrew Syntax (Winona Lake, Ind: Eisenbrauns, 1990) sectoin 7.4.2.

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What is meant by being brought "back in ships to Egypt"? Did this happen historically?

I find no reason from the text in question to assume that the Lord's threat to "send you (national Israel) back to Egypt in ships" is anything but literal. I take it to mean specifically the nation as a whole because the entire address regarding the Blessings and the Curses in Deut. 28:1 says; "If you fully obey.., the Lord will set you high above all nations of the earth." Then verse 15 begins; "However, if you do not obey,..,"

In other words; a partial return of Jews to Egypt cannot be the fulfillment of this prophecy. The times in history that we find a measure of the Jewish population returning to Israel via land or ship cannot fully satisfy the force of the prophecy; nor can it be surmised that it was the Lord himself who sent them to Egypt.

Furthermore, the other parts of the prophecy from Deut. 28:64-68 do not align with any known historical return to Egypt: 1) Scattered among all nations from "one end of the earth to the other" v.64. 2) There, from among those nations the Lord will give them no repose, a despairing heart, constant suspense, dread day and night, terrors in their heart and before their eyes, etc. vss.65-67. 3) And most remarkably, the Israelites will then offer themselves as slaves but no one will buy them! vs. 68. Therefore, vss. 64-67 must precede returning to Egypt in ships and vs. 68b must follow it in order for this specific prophecy to be fulfilled.

By and large, the Jews have found great comfort and ease in their diaspora surroundings even throughout their sad history of pogroms including 586 bc and 70 ad. None the less, the prophecy regards the entire nation of Israel and such an all inclusive prophecy has not been seen in the historical record. I find that Ezekiel's prophecy in 20:32-38 is most likely a prophecy of the same event which has surely not yet happened.

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Yes, they did go back, we just don't know how. There are so many verses which indicate that God knew they would transgress, and therefore would be forced back to Egypt again.

There is no archeological evidence of the books of Joshua, no invasions, no great Davidian empires, or empires of Solomon in archeological records.

All we have is the Hyksos people as a contender for the true Israelites, who suddenly dissapeared after their exodus from Egypt.1

According to the IVP Old Testament commentary:

Assyrian kings of the seventh century coerced their vassals into supplying troops for their military campaigns. One way then for Israelites to return to Egypt in ships would be in the Assyrian campaigns launched from the Phoenician coast in which they were obliged to take part. This represents continued oppression by foreign enemies, as the curses have detailed. Another possibility would include falling victim to Egypt’s slave trade in Syro-Palestine, where the slaves were often transported by ship.

Footnotes

1 It is not certain that the Hyksos were indeed the Israelites, however. According to the Jewish Virtual Library:

The Hyksos are not mentioned explicitly in the Bible, but some reminiscences of them can be detected. The connection made by Josephus and Manetho with the exodus is correct to the extent that the traditions of descent into Egypt and exodus therefrom were at least in part inspired by distant memories of the Hyksos movements (Redford). There are two instances where the history of the Hyksos is connected with Palestine. The first is during the beginning of their penetration into Egypt, since their domination over Lower Egypt must have been preceded by control over Palestine. The second is during the decline of the Hyksos, when they were expelled from Egypt by the rulers of the 18th Dynasty northward toward southern Palestine. It is not surprising, therefore, to find signs which distinguish the culture characteristic of the rule of the Hyksos in Egypt and in Palestine.

D. Redford, Egypt, Canaan and Israel in Ancient Times (1992)

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    This post was edited to help bring it into conformity with site standards. Please review.
    – Dan
    Sep 3, 2013 at 18:05
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"And the LORD shall bring thee into Egypt again with ships, by the way whereof I spake unto thee, Thou shalt see it no more again: and there ye shall be sold unto your enemies for bondmen and bondwomen, and no man shall buy you."

Moses told the Israelites that:

"The LORD will bring you and your king whom you set over you to a nation that neither you nor your fathers have known. And there you shall serve other gods of wood and stone.... Because you did not serve the LORD your God with joyfulness and gladness of heart, because of the abundance of all things, therefore you shall serve your enemies whom the LORD will send against you, in hunger and thirst, in nakedness, and lacking everything. And he will put a yoke of iron on your neck until he has destroyed you. (Deut. 28:36, 47–48)"

"And Moses said unto the people, “Remember this day in which ye came out from Egypt, out of the house of bondage; for by strength of hand the Lord brought you out from this place. There shall no leavened bread be eaten." (Exodus 13:3)

As you can see Egypt is the House of Bondage. The "IT" they would see no more is Israel and the enemies they would be sold to are the Edomites. They were sold as slavemen and slavewomen. (They were sold by their enemies the Africans and the Arabs.)

The word "buy" in this verse is an old Quaker word meaning to Redeem! To Redeem means to free from captivity by payment of ransom. So no one would pay the ransom to free them from captivity.

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"According to Josephus, it had been the earnest desire of Titus to preserve the Temple, but his commands were disobeyed by his soldiers in the fury of the struggle. According to Sulpicius Severus, on the other hand, who is probably quoting the very words of Tacitus, Titus formed the deliberate purpose to destroy Christianity and Judaism in one blow, believing that if the Jewish root were torn up the Christian branch would soon perish. The tallest and most beautiful youths were reserved for the conqueror’s triumph. Of those above seventeen years of age multitudes were doomed to work in chains in the Egyptian mines."

From Frederick W. Farrar, The Early Days of Christianity (1882), Volume II, Chapter VII.

Titus had these slaves transported to Egypt in ships, fulfilling Deuteronomy 28:68.

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