The following is a brief summary of some of thoughts on the parsha that R' Frand spoke about in his shiur tonight. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand began the vort by noting that the parsha takes a dramatic turn towards the end of the sedra when Yosef and Binyamin meet. In Bereishis 43:30, the Torah states - וַיְמַהֵ֣ר יוֹסֵ֗ף כִּֽי־נִכְמְר֤וּ רַֽחֲמָיו֙ אֶל־אָחִ֔יו וַיְבַקֵּ֖שׁ לִבְכּ֑וֹת וַיָּבֹ֥א הַחַ֖דְרָה וַיֵּ֥בְךְּ שָֽׁמָּה - Yosef went quickly because his mercy was arisen by seeing his brother and he went into another room to cry.
Rashi relates the dialogue between Yosef and Binyamin when they met, as Yosef asked Binyamin whether he had any brothers from his mother and Binyamin said "yes." Thereafter Binyamin told him of his ten sons and that each had been named for aspects of Yosef's life. Some of these names were descriptive such as Becher as Yosef was the first born and Na'aman because he was pleasant. Other names related to the troubles that befell Yosef such as Bela, since Yosef was swallowed up by the other nations.
R' Frand quoted the Tolner Rebbi who asks - why is it that Na'aman was the name of Binyamin's fifth child? After all, the quality that Yosef was pleasant was not minor, this should have been first or second!
R' Frand then digressed to discus what it means to be pleasant. He quoted a Gemara in Sanhedrin in which R' Oshaya said that he had two staffs - one he called Naim and one he called Chovlin (damager). The Naim were the talmidei chachamim who lived in Israel and pleasantly discussed the Torah together. Chovlin on the other hand were those who lived in Bavel and who were combative and spirited in their discussion of Torah.
R' Frand then told a story of R' Menachem Zumba (sp?) who had spoken at the Third Knessia (R' Frand compared it to an Agudah convention) prior to WWII. R' Zumba was not one of the first speakers and many of the speakers who came before him spoke critically of certain issues. When R' Zumba spoke he began by stating וַיִּשְׁמַ֞ע יִתְר֨וֹ and quoting Rashi who asks why was he called Yisro when he had all these other names? Because due to Yisro there was another parsha added to the Torah - the parsha of וְאַתָּ֣ה תֶֽחֱזֶ֣ה. But why did Rashi call it by that name when Yisro also said לֹא־טוֹב֙ הַדָּבָ֔ר אֲשֶׁ֥ר אַתָּ֖ה עֹשֶֽׂה four pesukim earlier? He answered that everyone is capable of complaining and criticizing, but the person who has the solution and positive guidance is to be lauded.
Yosef had the quality of being pleasant, but he also was forced to endure trouble after trouble - being hated by his brothers, being thrown into a pit, sold down to Egypt, thrown in jail. These are things that could cause a person to lose his pleasant disposition. Yet, even after all of these events, when he sees Pharaoh's two servants thrown in jail he says to them in a pleasant way (Bereishis 40:7) - מַדּ֛וּעַ פְּנֵיכֶ֥ם רָעִ֖ים הַיּֽוֹם - why are your faces sad today? Because even after all his troubles, he was pleasant to others. And this is why the name pleasant came fifth, after the description of being first born and three of his troubles.
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