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The Midrash tells a strange story:

When Moses said to Jethro, "Give me your daughter Tzipporah as a wife", Jethro answered, "If you do what I ask of you, I will give her to you as a wife." Moses said: "What do you ask?" Jethro replied: "Your first son must serve idolatry. The following sons may serve God in heaven." Moses accepted. Jethro said: "Swear." And Moses swore. [Mechilta d'Rabbi Yishmael 18:3]

Now, we learned later [Judges 18:30; Avot d'Rabbi Natan 34:4] that the son of Moses' son Gershom indeed became an idolater. But why would Jethro make such a request in the first place? Didn't God Himself tell Moses to welcome Jethro into Judaism with great honor [Midrash Tanhuma, Yitro 6] ?

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  • Could you clarify what problem you see from Midrash tanchuma? I think I understand but it's a little vague
    – robev
    Commented Jul 5, 2020 at 2:23
  • That God knew Jethro's heart was in the right place.
    – Maurice Mizrahi
    Commented Jul 5, 2020 at 13:35
  • Maybe it was? Your Mechilta is describing 60 years earlier...maybe he did teshuva
    – robev
    Commented Jul 5, 2020 at 14:42

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Rabbi Schwab explains that Yisro wanted at least one grandson to take the path he did which was worship all avoda zara and recognizing the worthlessness and ultimately come to recognize Hashem as the one true Power. He believed this would give a better appreciation of Hashem. Moshe would not have preferred this type of chinuch, as it opens the door for trouble, but agreed.

See Mayan Beis Hashoeva on Yisro 18,4.

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  • Did nobody before Rabbi Schwab (1908-1995) say anything about the matter? That would be surprising.
    – Maurice Mizrahi
    Commented Jul 5, 2020 at 21:15
  • Someone else who discusses it is Toras Moshe daf 89a as brought in the Bris Avraham on Yalkut Shimoni. Unfortunately he didn't quote or paraphrase what he said. In fact he didn't even specify which Toras Moshe he was referring to. I wasn't able to find a match from this lead in the sefarim on HebrewBooks. Perhaps someone else will have more success.
    – user6591
    Commented Jul 5, 2020 at 21:40

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