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On the one level, I might think he didn't since why would the king keep track of Haman's personal vendettas. However, when he tells Haman to go honor Mordechai, he tells him exactly where to find him - at the gate. This would imply that he keeps some sort of tabs on the gate. If this were true, he had to have known at the very least, that Mordechai has been refusing to bow to Haman.

Did he somehow miss this? Did he know and not care? Was he purposely getting in a jab at Haman making him do this to Mordechai knowing how much it would pain him inside? Was this a show of power over Haman to make sure he didn't let his head get too big?

  • at the gate is an appointed position of judge. Just because he knew that Mordechai was a sitting judge (especially after it was read to him in the chronicles), doesn't mean he knew anything more about it. Also, see the Talmud's explanation of why the king referred to Mordechai as the jew who sits at the kings gate: sefaria.org/Megillah.16a.4?lang=bi&with=all&lang2=en – Menachem Mar 15 at 4:07
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Rabbi Yonasan Eyebeschutz in Ya'arot Devash, states that Haman carefully put his request in terms of the Jews as a nation in order to make sure that Achashveros would accept his attempt and would wipe out all the Jews. He did not want Achashveros to realize that it was because Mordechai (who was the only Jew in the forbidden city) was refusing to bow down to him. Achashveros would have gotten suspicious and investigated the circumstances. This could have led to him finding out that Haman had been Mordechai's slave and removing him from power.

As far as Haman being chosen to lead Mordechai and honor him, it was because he was so anxious to have Mordechai killed that he made sure to be in the outer courtyard before the king was awake in order to be the first person that the king saw. The king had been so disturbed that he called for anyone who was ot there.

Megillas Esther 6:4

And the king said, "Who is in the court?" And Haman had come to the outside court of the king's house, to petition the king to hang Mordecai on the gallows that he had prepared for him.

The king never gave Haman a chance to say anything before asking

"What should be done to a man whom the king wishes to honor?"

Of course Haman thought

"Whom would the king wish to honor more than me?"

and forgot all about asking for permission to kill Mordechai and stated what he wanted for himself.

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Esther Rabbah 7:20 surprisingly teaches us that Achashverosh hated the Jews MORE than Haman:

וַיָּסַר הַמֶּלֶךְ אֶת טַבַּעְתּוֹ וַיִּתְּנָהּ לְהָמָן" (אסתר ג:י) רַבָּנָן אָמְרִין אֲחַשְׁוֵרוֹשׁ שׂוֹנֵא אֶת יִשְׂרָאֵל" יוֹתֵר מֵהָמָן הָרָשָׁע

"The king removed his signet ring from his hand and gave it to Haman." (Esther 3:10) Our Rabbis teach us that Achashverosh hated the Jews more than Haman the wicked

Knowing this we can perhaps assume that either:

Achashverosh knew about Haman's hatred of Mordechai OR he didn't know but wouldn't have cared (may have even been supportive!)

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