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Is there a source to connect (mystically, or otherwise) those enemies of the Jews (presumably Amaleki) killed in Megillas Esther 9:12 with the 500 men from the tribe of Shimon who killed out the remainder of the Amaleki in Divrei Hayamim I 4:42-43?

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If there isn't, there should be. –  avi Feb 25 '12 at 16:54
    
you can read this doc(hebrew) from harab reoven rivlin its connect all the wars againts amalek, google.com/… –  Haim Evgi May 10 '12 at 12:13
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2 Answers

The shiur that was referenced states that the reishish chochma says that Mordechia donned sak (sackcloth) which is gematria 400 to counteract Eisav (who attacks the Jews with 400 men). The sak leads to tzayis (listening) which is gematria 500. The magid shiur then pairs this with the pasuk (in ki sisa) kach lecha besamim mor dror (mordechai) chamesh meos (500). This all parallels the 500 people killed by the Jews in shushan.

He doesn't mention anything about Shimon and those 500 men but it would fit very well with what he was saying (someone should tell him). Especially because Shimon is related to shmiyah (listening)

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vram, thanks for your answer, and welcome to Mi Yodeya. I hope you stick around and enjoy the site. –  msh210 Jun 1 '12 at 16:47
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Listen to this shiur which discusses this idea: http://www.filefactory.com/file/7gdq80su0oxb/n/Drasha_Purim_RCK_-Purim_2012_mp3

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A summary would be nice. –  Double AA May 31 '12 at 19:21
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What @DoubleAA said. Plus bibliographic information (who spoke?). –  msh210 May 31 '12 at 19:39
    
It's a recording of me speaking at my Purim Seudah –  Reb Chaim HaQoton Jun 1 '12 at 7:56
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