Based on the writings of Nehama Leibowitz
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.
It would seem that based on the text, 39 - 1 “...And Potiphar... bought him from the hand of the Ishmaelites” that the final sale of Joseph was executed by the Ishmaelites. Therefore the suggested sequence of brothers -> Midianites -> Ishmaelites would fit in well with the above verse. Rashi posits the sale sequence differently because he follows the explanation of Onkelos who translates the brothers’ reaction to Judah’s suggestion that they sell Joseph to the Ishmaelites as “they hearkened to his words” i.e. they obeyed him. Thus the brothers did the selling to the Ishmaelites as step 1 in Josheph’s eventual journey to Egypt. The author of the work Tzedah La’derech answers Mizrahi’s question as to how Rashi would explain verse 39 -1 that Potiphar bought Joseph from the Ishmaelites, by citing the Midrashim, Midrash Bereshit Rabbah 86 - 3 and Tanhuma Vayeshev 15 which explain that Potiphar consulted the Ishmaelites to verify that the Midianim didn’t kidnap Joseph.
“His brothers heard”: implying they accepted his view. The Hebrew shema “hear” wherever it implies agreement, as in Gen. 28, 7 and the phrase na’aseh ve-nishama is translated by Onkelos as “we shall accept.” But wherever it implies hearing with the ear as in Gen. 3, 8; 27, 5; 35, 22 it is translated by Onkelos by the word shema. Rashi Rashi always explains the meaning of a word whether by resort to the Aramaic Targum Onkelos or to another example in the Bible or by translation into the vernacular (Old French), the first time he comes across it. Why then did Rashi wait till our sidra to explain this connotation of the Hebrew word shema instead of in Gen. 38, 7, where it first appears and on which he indeed bases himself?
In Bereshit 28 - 7 “And Yaakov heeded his father and mother... it is clear from the context that Va’yishma means obeyed rather than simply an auditory response because the verse concludes with the words “and he went to Padan Aram.” Thus it is not necessary for Rashi to offer any insight on the meaning of Va’yishma. In our Parasha 37 - 27 the words “Va’yish’m’u ehav” could be translated either way: The brothers simply listened to Yehuda’s advice but didn’t follow it, or the brothers heeded his advice and sold Joseph. Thus Rashi’s comment is necessary here in order to give the Torah student an understanding of what transpired.
Prepared by: Rabbi Mordechai Spiegelman veteran yeshiva educator (USA) now residing in Jerusalem