Midrash Esther IV: The Headache Maker
Rabbi Levi and the Rabbis differed on who Achashveirosh really was. Rabbi Levi said: Achashveirosh is the same as Artaxerxes; (Achashveirosh was a nickname)and why was he called Achashveirosh? Because no one could mention him without feeling a headache. “Ach l’rosh,” – “Woe to my head!”
The Rabbis said: Artaxerxes was the same as Achashveirosh, meaning Artaxerxes was the nickname; and why was he given this nickname? Because he used to fall into a passion and then be sorry. Some commentaries explain this final phrase in a different manner: he was called Artaxerxes because he would upset people and, by doing so, would weaken their resolve.
Rabbi Levi seems to be saying that by the time our story begins, in the book of Esther, when he is referred to as Achashveirosh, he already had his derogatory nickname. People were already describing him as a “headache maker.”
This means that we must read the story from its very beginning as that of a king who is a burden to his people. This would mean that even the half-year conference that he ran in Shushan, and and the seven-day party that followed, despite all the luxuries and personal attention, were attended by people who saw Achashveirosh as the source of their headaches. This would mean that by the time the King wanted to deal with Vashti, people just viewed it as another headache. The gathering of the women so he could choose a queen; another headache. The appointment of Haman; another headache. The letter signed by Haman; another headache.
The letter signed by Mordecai; at first just another headache, but if you carefully read the text you will see that people saw in Mordechai’s appointment a chance for some stability. An opportunity to live without the constant headaches. This is also a hint to why Achashveirosh felt so threatened by Mordecai, why it would be Mordecai’s supporters who plotted to assassinate the King, why Haman fel safe decreeing the massacre of Mordecha’s supporters, and why Achashveirosh ultimately knew that he had to turn to Mordechai for help when things were so unstable.