The following is a brief summary of some of thoughts said over by R' Daniel Glatstein in a shiur on Torah Anytime (https://torahanytime.com/lectures/353913) on Purim a few weeks ago. This is not a literal transcription but just a summary of some of the shiur that I found meaningful. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Glatstein.
The shiur focused on a question about a pasuk in the Megillah (7:4) כִּ֤י נִמְכַּ֨רְנוּ֙ אֲנִ֣י וְעַמִּ֔י לְהַשְׁמִ֖יד לַֽהֲר֣וֹג וּלְאַבֵּ֑ד וְ֠אִלּ֠וּ לַֽעֲבָדִ֨ים וְלִשְׁפָח֤וֹת נִמְכַּ֨רְנוּ֙ הֶֽחֱרַ֔שְׁתִּי כִּ֣י אֵ֥ין הַצָּ֛ר שֹׁוֶ֖ה בְּנֶ֥זֶק הַמֶּֽלֶךְ. Why is it that Esther offered that if only the Jews had been sold into slavery, she would have kept quiet?
To address this, R' Glatstein began with an analysis of why the Jews were punished in the Purim story. He quoted the Gemara in Megillah where R' Shimon Bar Yochai asked his students why the Jews were punished. They offered that it was because they ate at the party, but he responded - then only the Jews of Shushan should have been punished. They suggested that it was because they bowed down to Nevuchadnezzar, but he responded - then they should have killed then. He then answered that they did not mean to serve idols, it was done outwardly, for the same reason the decree in Purim was outwardly.
However there is 3rd sin which was the cause of the Purim story. R' Glatstein quoted the Sefer Zecher Dovid from R' Dovid of Modina - the two in the Gemara and the third is Mechiras Yosef. This concept is also found in Medrash Rabbah on Esther (3:15) וְהַמֶּ֤לֶךְ וְהָמָן֙ יָֽשְׁב֣וּ לִשְׁתּ֔וֹת וְהָעִ֥יר שׁוּשָׁ֖ן נָבֽוֹכָה. The Medrash states that anyone who thinks Hashem overlooks sin, Hashem will overlook their life. Hashem said to the tribes - you sold Yosef and were eating and drinking - this will happen now. But why? Yosef was mochel them!
The Yalkut Shimoni gives the same reason as does the Alshich. The Chida explains why now the punishment came for Mechiras Yosef and not at some point during the thousand plus years between Mechiras Yosef and Purim. He begins by noting that the hatzalah had to come from Binyamin (Esther/Mordechai) because they were not involved in Mechiras Yosef. He also quoted the Medrash that when the decree came in the Purim story, Eliyahu HaNavi went to wake up Moshe to ask him to pray for them to be saved, because Moshe is most deeply connected with Yosef. He also observed that when the Jews were saved in the Megillah (7:10) - וַֽחֲמַ֥ת הַמֶּ֖לֶךְ שָׁכָֽכָה - the Gematria of שָׁכָֽכָה is the same as Moshe.
R' Glatstein then went through the numerous parallelisms between Parshas Mikeitz and Megillas Esther. The reason for this connection is that the sin of Mechiras Yosef was the cause of the decree.
But why now? He quoted the Sefer Zera Berech who explains that the meat at the party was Ever Min HaChai and Gilui Arayos was going on at the party. These were the same issues that the brothers had before the sale of Yosef. He also quoted the Shvilei Pinchas who said that while Yosef forgave his brothers, but when the sin which was the cause happens again in the generation - the punishment is reawakened. Haman pointed out in Esther 3:8 - יֶשְׁנ֣וֹ עַם־אֶחָ֗ד מְפֻזָּ֤ר וּמְפֹרָד֙ and when Haman pointed out that the Jews were not getting along it reawakened the punishment.
When Moshe was reawakened by Eliyahu HaNavi he asked whether the decree was written in cement or in blood? Eliyahu responds that it was in cement. R' Glatstein told a story of an Ani who came to R' Chaim Volozhner and asked for Tzedakah. He gave a coin and then the Ani asked for an additional coin and promised a dvar Torah that R' Chaim had never heard. He explained - how do we see that the decree was not in blood - because it states יִכָּתֵ֖ב לְאַבְּדָ֑ם - which can be read Lo B'Dam. And after he gave him the coin, R' Chaim realized that he was Eliyahu HaNavi.
But what was the debate? For over 1000 years the Jews had a question about whether they would be responsible for throwing Yosef into a cement pit or for his blood? Because if someone is sold into captivity it is like killing them. And Eliyahu said no - its only cement.
And this is what Esther tells Achasveros - we know that we should be punished with cement - that we should be sold into slavery for Yosef being sold. But now that the decree is that we should be killed - for that I can't keep my mouth shut. Esther is disclosing to him - we know that we did something wrong by selling him and if we had been sold, it would be deserved. But if they are coming for our blood, for that I can't.
R' Glatstein noted that Haman is also called מְמֻכָ֗ן which the gematria is the same as Yosef. And when Haman paid his Sheklaim he is reawakening the punishment for Mechiras Yosef. So we give Machtzis HaShekel to show that each person is incomplete and two halves make us whole.
R' Glatstein also quoted a Yerushalmi which quotes Resh Lakish who states that Pidyon Haben is to atone for Mechiras Yosef because each of the tribes took a coin for the sale of Yosef. And similarly Resh Lakish is quoted in Medrash Tanchuma as stating that the Machtzis HaShekel is to atone for the sale of Yosef. These Shekalim that we collect and read about on Rosh Chodesh Adar is to be in advance of Haman's giving of the Shekalim to Achasverosh.
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