The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. 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 Rashi explains that the כְּתֹ֥נֶת פַּסִּֽים has an allusion to the troubles that befell Yosef as the word פַּסִּֽים is an acronym for four troubles - Potiphar, Socharim, Yishmaelim and Midyanim.
R' Frand then quoted the Sefer Abir Ya'akov which asked why we invoke the כְּתֹ֥נֶת פַּסִּֽים during the final chanting of the Kohanim during Birkas Kohanim. The prayer which is said silently states that Yosef engendered Chen and Chessed after being given the Kesones Passim, but the pesukim tell a different story!
R' Frand prefaced his answer by quoting a story of R' Ruderman who used to visit with R' Chaim Ozer when R' Ruderman was a young man. When their meeting ended, R' Chaim Ozer would walk with him from his home for a few blocks. At that point he would say good bye, but R' Ruderman did not want him to walk back by himself, so he would walk R' Chaim Ozer back to his house. This repeated itself a few times before R' Ruderman finally went home by himself.
R' Frand said that R' Ruderman would tell this often, and he would mention how important this made him feel, that R' Chaim Ozer did not do this with all his guests, so he must have seen something in the young R' Ruderman that he wanted to foster.
When Ya'akov gave the כְּתֹ֥נֶת פַּסִּֽים to Yosef it was not just a splendid garment. It was a way that Ya'akov could show Yosef how important he was to him and that he saw that Yosef could succeed.
R' Frand said that this gave Yosef an air of confidence, such that wherever he went in Egypt - from Potiphar's house to prison, he was entrusted with positions of authority - based on how he carried himself.
This can also be seen in the language of the prayer in Birkas Kohanim as it specifically mentions - when his father clothed him in the כְּתֹ֥נֶת פַּסִּֽים.
It can also be seen in the way that the coat was taken away, as the Torah uses multiple description in Bereishis 27:23 - וַיַּפְשִׁ֤יטוּ אֶת־יוֹסֵף֙ אֶת־כֻּתָּנְתּ֔וֹ אֶת־כְּתֹ֥נֶת הַפַּסִּ֖ים אֲשֶׁ֥ר עָלָֽיו.
R' Frand linked this to a Gemara in Yoma which writes that a Rasha when he will be judged cannot claim that his good looks were the reason that he was promiscuous. He will then be asked - were you more handsome than Yosef? Yet he was able to resist, why can't you?
But the Gemara also teaches that when Yosef was tempted and considered giving in, he saw the image of his father and resisted. But for anyone if they were shown this when tempted they would also resist!
R' Frand answered that Yosef conjured this image himself - he thought about his father and Ya'akov's confidence in him and used this to resist her.
R' Frand said a second vort based on the pasuk in Bereishis 39:20 - יִּקַּח֩ אֲדֹנֵ֨י יוֹסֵ֜ף אֹת֗וֹ וַיִּתְּנֵ֨הוּ֙ אֶל־בֵּ֣ית הַסֹּ֔הַר מְק֕וֹם אֲשֶׁר־אֲסִירֵ֥י הַמֶּ֖לֶךְ אֲסוּרִ֑ים וַֽיְהִי־שָׁ֖ם בְּבֵ֥ית הַסֹּֽהַר - why the second use of being present in the prison?
R' Frand again quoted the Abir Ya'akov who notes that a person may undergo a personal trouble which causes them to lose the ability to learn as much, or requires them to work longer hours for the same money, or something else that reduces the time that can be spent on spiritual matters. The person may say - but I was learning so much or so long, why did Hashem take me from that? R' Frand answered that the person needs to realize that Hashem put me in this position because he wants me to do other things and not spend as much time on learning or spiritual matters. He must realize, I am in this place because Hashem wants me here - וַֽיְהִי־שָׁ֖ם בְּבֵ֥ית הַסֹּֽהַר.
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