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.
In Bereishis 24:15 the Torah writes "וַֽיְהִי־ה֗וּא טֶ֘רֶם֘ כִּלָּ֣ה לְדַבֵּר֒ וְהִנֵּ֧ה רִבְקָ֣ה יֹצֵ֗את" but the Torah does not identify the subject of the "ה֗וּא." The Rabbeinu B'Chaye states that the "ה֗וּא" is an angel, but this seemingly creates additional questions as there is no angel mentioned in the story.
R' Frand also raised the famous question of the use of the word הָעֶ֖בֶד and הָאִ֔ישׁ at differing points in the story as pronouns for Eliezer. Why does the Torah begin with calling him הָעֶ֖בֶד and then later הָאִ֔ישׁ before returning to הָעֶ֖בֶד?
R' Frand, again quoting the Rabbeinu B'Chaye explains that after Eliezer came to the well and made the condition that whomever would offer water for his camels would be the woman chosen for Yitzchak - he immediately met Rivkah. This is exactly when the ה֗וּא is mentioned, because Hashem then caused the angel to instigate that Rivkah would appear. It is at this point that Eliezer transitions to הָאִ֔ישׁ, based on his interaction at the well. Only later after the mission is completed in that Rivkah's family agrees that she can travel back with Eliezer that he again is called הָעֶ֖בֶד.
R' Frand said a second vort from a Sefer written by Nat Lewin's father, R' Aharon Lewin - the Reisha Rav. He began by quoting Rashi which states that all of Sarah's life was equally good. But how is this to be understood? She marries Avraham and then immediately moves to Canaan. Then there is a famine and they travel to Egypt where she is taken captive and later again she is taken captive by Avimelech. Later she has the indignity of seeing Hagar have a child while she is barren and then Hagar treats with her disdain. Finally she has Yitzchak and has the fright of him being offered at the Akeidah. How is this good?
R' Lewin answers that Sarah saw her life with its peaks and valleys, but accepted that it was all for the best.
R' Frand then quoted a Medrash which states that R' Akiva was giving a derasha when he saw that people were Misnamnem (commonly translated as dozing). He wanted to awaken them and he said why did Esther rule over 127 lands? Because she is the granddaughter of Sarah who lived 127 years.
But is this a gezeira shava? What is the connection between the 127? R' Frand quoted R' Lewin who said that the connection was Esther's attitude. She lost both of her parents and was orphaned before being taken in by Mordechai. But then she is forced into the "beauty pageant" for Achasverosh and later taken as his bride. But much like Sarah - she recognized that everything is from Hashem and it is all for the good.
R' Frand then circled back to R' Akiva. He noted that R' Akiva lived at the end of the Beis Hamikdash era and things were going quite poorly for the Jewish people. He saw that they were down and he wanted to wake them up. To do this he remarked about Sarah and Esther and how they did not get depressed over the troubles that befell them and R' Akiva sought to "wake up" the people by giving them a positive outlook as well.
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