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According to the Torah, the Israelites killed all of the kings of Midian and all males and all but the youngest girls and took all of their possessions (Parashat Mattot - B'midbar 31:7-10).

וַיִּצְבְּאוּ עַל מִדְיָן כַּאֲשֶׁר צִוָּה ה' אֶת מֹשֶׁה וַיַּהַרְגוּ כָּל זָכָר

וְאֶת מַלְכֵי מִדְיָן הָרְגוּ עַל חַלְלֵיהֶם אֶת אֱוִי וְאֶת רֶקֶם וְאֶת צוּר וְאֶת חוּר וְאֶת רֶבַע חֲמֵשֶׁת מַלְכֵי מִדְיָן וְאֵת בִּלְעָם בֶּן בְּעוֹר הָרְגוּ בֶּחָרֶב

וַיִּשְׁבּוּ בְנֵי יִשְׂרָאֵל אֶת נְשֵׁי מִדְיָן וְאֶת טַפָּם וְאֵת כָּל בְּהֶמְתָּם וְאֶת כָּל מִקְנֵהֶם וְאֶת כָּל חֵילָם בָּזָזוּ

וְאֵת כָּל עָרֵיהֶם בְּמוֹשְׁבֹתָם וְאֵת כָּל טִירֹתָם שָׂרְפוּ בָּאֵשׁ

How was Midian then able to cause so much trouble for Israel later (during the period of the Judges, Ch 6-7)?

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Since your question is solid, I think we have to read the pasuk like this:

וַֽיִּצְבְּאוּ֙ עַל־מִדְיָ֔ן ... וַיַּֽהַרְג֖וּ כָּל־זָכָֽר [שהם פגשו]׃ ... וְאֵ֤ת כָּל־עָרֵיהֶם֙ [שהם פגשו] בְּמ֣וֹשְׁבֹתָ֔ם וְאֵ֖ת כָּל־טִֽירֹתָ֑ם [שהם פגשו] שָׂרְפ֖וּ בָּאֵֽשׁ׃

They took the field against Midian,...and slew every male [that they encountered]... And they destroyed by fire all the towns [that they encountered] in which they were settled, and their encampments[that they encountered].

So "all" does not refer to "all Midyan has" but to "all they encountered"

Still, if we do math with the captives, it's a huge hit.

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