Why was Yoseph sold to Ishmaelites and then Midianites, rather than Midianites and then Ishmaelites?

Question

The following question and translations are courtesy of Studies in Bereshit by Nechama Leibowitz.

In Parshat Vayeshev, some pesukim suggest that Yoseph was sold by his brothers to Midianites, and others to Ishmaelites. The Ishmaelites are mentioned first ("Behold, a caravan of Ishmaelites...") followed by "And there passed by Midianites, merchants; and they lifted up Yoseph out of the pit and sold Yoseph to the Ishmaelites). This is followed by a third group known as Medanites (which Rashi suggests is simply an abbreviated form of Midianites) selling Yoseph to Mitzrayim, and ultimately concludes with the Ishmaelites selling Yoseph to Potiphar.

Rashi suggests that Yoseph was first sold by his brothers to the Ishmaelites. The Ishmaelites then sold Yoseph to Midianites AKA Medanites, who eventually sold Yoseph to Potiphar in Mitzrayim. Thus, when it says the brothers sold Yoseph to the Medianites or that the Ishmaelites sold Yoseph to Mitzrayim, the Torah is speaking of indirect action/figuratively.

This is all well and good, but Studies in Bereshit proposes the following question:

The following objections have been raised to Rashi's interpretation: What forced Rashi to explain that the brothers sold him to the Ishmaelites and the latter to the Midianites and not that the brothers sold him to the Midianites and the latter to the Ishmaelites, which would fit the text better? Explain which texts this explanation would suit better and why Rashi, in spite of this, preferred his explanation.

Try as I might, I was not able to come to any conclusions with this question - or, indeed, any manner in which the order would be significant at all! Mayhaps there is some connection between the tribes and Ishmael that is significant here, but I am not sure what it would be. I agree that the text is smoother if the order was brothers -> Midianites -> Ishmaelites -> Potiphar, as it refers to selling Yoseph right after the Midianites pass by, and says that Potiphar bought Yoseph "from the hand of the Ishmaelites" which suggests that there was direct interaction between Potiphar and the Ishmaelites. However, I can think of no reason why Rashi would forego this in favor of the order he proposes. Why does Rashi prefer the order he gives (brothers -> Ishmaelites -> Midianites -> Potiphar), rather than the one his objectors give (brothers -> Midianites -> Ishmaelites -> Potiphar)?

Answer 1

Doesn't the posuk itself give the order of brothers -> Ishmaelites -> Midianites -> Potiphar and not brothers -> Midianites -> Ishmaelites -> Potiphar ?

Breishis 37:27-28 says לְכ֞וּ וְנִמְכְּרֶ֣נּוּ לַיִּשְׁמְעֵאלִ֗ים וְיָדֵ֨נוּ֙ אַל־תְּהִי־ב֔וֹ כִּֽי־אָחִ֥ינוּ בְשָׂרֵ֖נוּ ה֑וּא וַיִּשְׁמְע֖וּ אֶחָֽיו וַיַּֽעַבְרוּ֩ אֲנָשִׁ֨ים מִדְיָנִ֜ים סֹֽחֲרִ֗ים וַיִּמְשְׁכוּ֙ וַיַּֽעֲל֤וּ אֶת־יוֹסֵף֙ מִן־הַבּ֔וֹר וַיִּמְכְּר֧וּ אֶת־יוֹסֵ֛ף לַיִּשְׁמְעֵאלִ֖ים

Come, let us sell him to the Ishmaelites, and our hand shall not be upon him, for he is our brother, our flesh." And his brothers listened. And Midianite merchants, passed by, and they pulled and lifted Joseph from the pit, and they sold Joseph to the Ishmaelites for twenty silver

The Posuk is clear that they both intended and did sell him to the Ishmaelites . The Sifsie Chachomim adds that had it been the Midianites who pulled Yosef out of the Bor then the brothers would not have been the ones who sold Yosef. But they had to have some connection to the sale or the Posuk would not have mentioned their passing by at the time.(The amount of their involvement in the original and final sale of Yosef is a question discussed in the Rishonim)

A few pesukim later says that it was the Midianites not the Ishmaelites who sold him to Potiphar.

Breishis 37:36 וְהַ֨מְּדָנִ֔ים מָֽכְר֥וּ אֹת֖וֹ אֶל־מִצְרָ֑יִם לְפֽוֹטִיפַר֙ סְרִ֣יס

And the Midianites sold him to Egypt, to Potiphar, Pharaoh's chamberlain

The posuk explicitly says he was bought from the Midianites.