The brothers make their way to Egypt and do not recognize Yosef. Yosef, however, recognizes them and decides to toy with them. When the brothers reveal that Binyamin is back with Yaakov, Yosef uses this as a hook. He tells them that in order to prove they are not spies, they must bring Binyamin back. Yosef then takes Shimon captive as collateral.Why does he take Shimon?Rashbam recalls the story of Dina and Shechem. Yosef took Shimon to separate him from his brother Levi. The last time Shimon and Levi were paired up and angry, they massacred an entire city. This answer makes sense and shows that Yosef knew he had to separate the two.But why would he take Shimon and not Levi?Radak quotes the Midrash, which explains that Yosef took Shimon because Shimon was the one who threw Yosef into the pit. The fact that Yosef singled out Shimon is a sign that Shimon had done something worthy of Yosef’s wrath. The Midrash offers a compelling hypothesis, but this is not mentioned explicitly in the text.Perhaps the answer lies in the previous few verses. After Yosef lists his demands, the brothers panic. They cry out that this is direct punishment for having thrown Yosef into the pit and their scheme to harm him.Genesis 42:22וַיַּעַן רְאוּבֵן אֹתָם לֵאמֹר הֲלֹוא אָמַרְתִּי אֲלֵיכֶם לֵאמֹר אַל־תֶּחֶטְא֥וּ בַיֶּ֖לֶד וְלֹ֣א שְׁמַעְתֶּ֑ם וְגַם־דָּמֹ֖ו הִנֵּ֥ה נִדְרָֽשׁ׃Then Reuven spoke up and said to them, “Did I not tell you, ‘Do no wrong to the boy’? But you paid no heed. Now comes the reckoning for his blood.”Genesis 42:23וְהֵם לֹא יָדְעוּ כִּי שֹׁמֵעַ יוֹסֵף כִּי הַמֵּלִיץ בֵּינֹתָם׃They did not know that Yosef understood, for there was an interpreter between them.Genesis 42:24וַיִּסֹּב מֵעֲלֵיהֶם וַיֵּבְךְּ וַיָּשָׁב אֲלֵהֶם וַיְדַבֵּר אֲלֵהֶם וַיִּקַּח מֵאִתָּם אֶת־שִׁמְעוֹן וַיֶּאֱסֹר אֹתוֹ לְעֵינֵיהֶם׃He turned away from them and wept. But he came back to them and spoke to them; and he took Shimon from among them and had him bound before their eyes.Notice that Yosef goes to cry after Reuven admonishes the brothers, not after their admission of guilt. Yosef was not crying because of the brothers’ admission. He was crying because he realized Reuven had tried to stand up for him.After all, Reuven, as the firstborn, had the most to lose by saving Yosef, Yaakov’s favorite. All Yosef knew was that Reuven had been the one to throw him in the pit. He did not know his motivation. Hearing that his eldest brother tried to save him, Yosef decides to take the next oldest brother captive—Shimon.
