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I believe Jewish tradition states that many of the prophecies in Ki Tavo have transpired. Verse 68 says the following:

And the Lord will bring you back to Egypt in ships, through the way about which I had said to you, You will never see it again. And there, you will seek to be sold to your enemies for slaves and handmaids, but there will be no buyer.

Is this understood to have already been fulfilled? If so, when? If not, is it understood that it will be fulfilled in the future? Or is it because negative prophecies don't necessarily need to be fulfilled?

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There are a few possible solutions to this question.

Sabbahillel commented:

I have been told that the price of slaves dropped dramatically after the destruction of the second temple and Bar Kochva's revolt about 63 years later. I understand that many people consider that the fulfillment of that prophecy.

Ibn Ezra on this passuk (in brackets at alhatorah, as it was found only in the Paris 177 manuscript) suggests that this was fulfilled in the times of Mordechai and Esther, based on the wording of Esther in Esther 7:4:

כִּ֤י נִמְכַּ֙רְנוּ֙ אֲנִ֣י וְעַמִּ֔י לְהַשְׁמִ֖יד לַהֲר֣וֹג וּלְאַבֵּ֑ד וְ֠אִלּ֠וּ לַעֲבָדִ֨ים וְלִשְׁפָח֤וֹת נִמְכַּ֙רְנוּ֙ הֶחֱרַ֔שְׁתִּי כִּ֣י אֵ֥ין הַצָּ֛ר שֹׁוֶ֖ה בְּנֵ֥זֶק הַמֶּֽלֶךְ׃

for we are sold, I and my people, to be destroyed, to be slain, and to perish. But if we had been sold for bondmen and bondwomen, I had held my peace, for the adversary is not worthy that the king be endamaged. (JPS)

See also here: Is Esther's comment in Esther 7:4 a reference to one of the curses in Devarim 28:68?

The Seforno here has an alternate suggestion of what this Passuk means, and his interpretation is seen very clearly in our days (as well as throughout the ages):

וְהִתְמַכַּרְתֶּם – שֶׁתִּשְׁתַּדְּלוּ לַעֲשׂוֹת מִינֵי מְלָאכוֹת לְהִתְפַּרְנֵס בָּהֶן בְּקֶרֶב הָאֻמּוֹת. וְאֵין קנֶה – אֵין אִישׁ מֵהֶם חָפֵץ בִּמְלַאכְתְּךָ, כְּדֵי שֶׁלּא תּוּכַל לְהִתְפַּרְנֵס בָּהּ.

והתהכרתם, you will begin to manufacture or make by hand all kinds of goods the host country lacks in order to secure your economic well being, but ואין קונה, no one will buy these goods due to antisemitic reasons, as they do not want you to gain a foothold in their country.

Another clear fulfillment of this is noted by Rav David Zvi Hoffman here, who quotes Josephus saying that Titus sent 17,000 Jews to Egypt as slaves, as well as another possibility from the Jerome, who notes a Historical event that happened in the times of Hadrian. He does, however, note that it is unnecessary to show these events, and that they may simply refer to the general lower status of Jews:

טיטוס הרשע שלח (לדברי יוסף בן מתתיהו: מלחמת היהודים ו, ט׳:ב׳) 17000 יהודים למצרים לעבודת פרך. בזמנו של אדריאנוס קיסר נמכרו ליד קבר רחל בתור עבדים יהודים רבים לאין מספר (הירונימוס לירמיהו ל״א). אבל אין צורך לומר שנבואה זאת מתייחסת למאורע מסויים דווקא, אלא שבא הכתוב לומר שישראל ירדו, מפני שלא שמעו בקול ה׳, לשפל המדרגה, ובה יונח הגרעין לגאולתם.

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