Why is it that both Purim and Chanukah the heroes of their stories ended up losing out? That is Esther had no Jewish descendants as she married a non Jew (though her son was Jewish according to Halacha) but her son did not marry a Jewish woman so his children were not Jewish. Meanwhile Hamans children Taught Torah in Bnei Brak. As the Gemara States:

"מבני בניו של המן למדו תורה בבני ברק"

סנהדרין צו ע"ב

Then The Maccabees were killed out, and the Gemara says whoever says I am from the Children of the Maccabees is a slave or a liar As the Gemara states:

כל האומר מבית חשמונאי אני, או שהוא עבד או שהוא רמאי

בא בתרא ג, ב

The Heroes are the Biggest losers and these are our Rabbinic holidays why is this and what is the connection?

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    Well, it took around a hundred years, but the Maccabee/Hasmoneans pretty much did themselves in by infighting, allowing Herod's machinations to put himself and the Romans in charge...If Aristobulus and Hyrcanus had a united front together there would've been no Herod...maybe..but the Maccabee brothers themselves and the first John Hyrcanus did a glorious job of restoring Jewish nationhood, and deserve to be celebrated. – Gary Feb 27 '17 at 0:04
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    Did Esther not have children from a previous marriage? Also since when is she obligated in Pru Urvu that we care if she has kids? Also isn't Judaism passed on matrilineally? – Double AA Feb 28 '17 at 11:45
  • Moshe's descendant made and worshipped idols. As did many of David's. I don't know why this is so surprising. How do you know Esther didn't have daughters that stayed Jewish? Or sons from another previous marriage? Etc. The Pesukim tell us nothing. – Double AA Mar 6 '17 at 13:42
  • I'm pretty sure Rabbi J.B. Soloveitchik addresses an issue similar to this in his essay "Catharsis" – TrustMeI'mARabbi Mar 6 '17 at 15:00

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