Students of Hebrew will be delighted to know that the rabbis felt their pain in advance. Hebrew is an ambiguous language. And ambiguous phrases in the Hebrew text present an occasion for playful midrash (with a serious message).
Note: midrash (plural midrashim) refers to a kind of Jewish literature, written down primarily in the land of Israel in the third through sixth centuries (but also later and some from Babylon) offering Jewish creative interpretations of the Bible. In many cases these are shortened, memorizable forms with a history of being passed down orally which refer to sermons and colorful stories told by sages.
Take Ruth 1:1
וַיְהִי בִּימֵי שְׁפֹט הַשֹּׁפְטִים וַיְהִי רָעָב בָּאָרֶץ וַיֵּלֶךְ אִישׁ מִבֵּית לֶחֶם יְהוּדָה לָגוּר בִּשְׂדֵי מוֹאָב הוּא וְאִשְׁתּוֹ וּשְׁנֵי בָנָיו׃
That first phrase (va-yehee beemay shefoat ha-shoa-feteem) in the plain sense (using context and common sense as a guide) means, “It happened in the days of the judging of the Judges.”
What time period does that refer to? The plain meaning, it would seem to occur to any reader, is that this is the era when Israel was ruled by Judges.
But construct chains (word groups with an “of” relationship in Hebrew, as here “the judging of the judges”) can be read multiple ways. The phrase could also be taken to mean: “back when Judges were judged [by others].” In other words, it could refer to a time when people used to hold judgment on the Judges instead of obeying the judgments of the Judges!
The rabbis make a midrash on this with a serious moral:
So in the days when the judges judged, when a man had been guilty of idolatry and the judge wished to pass judgment on him, he came and flogged the judge, saying, “I have done to him what he wanted to do to me.” Woe unto the generation whose judges are judged! That is the meaning of the verse AND IT CAME TO PASS IN THE DAYS OF JUDGING OF THE JUDGES.
-Ruth Rabbah, Soncino Edition, Proem.