והנערה יפת תאר וטובת מראה “The maiden was shapely and beautiful.” (Esther 2:7)
The Gemara in Megillah (13a) quotes the opinion of Rav Yehoshua ben Karcha, who maintains that Esther was not inherently beautiful. In fact, she was a yerakrokes – she had a green complexion – but Hashem miraculously caused her to find favor in the eyes of everybody who saw her. The Gemara does not provide a source for Rav Yehoshua ben Karcha’s opinion, and it seems difficult to understand. If the Megillah explicitly testifies that Esther was physically attractive, for what reason did he denigrate her?
The Vilna Gaon explains that specifically Rav Yehoshua ben Karcha had no choice but to reinterpret the Megillah's statement about Esther’s appearance. The Gemara in Bava Basra (15b) records a dispute regarding when Iyov lived, and it quotes several opinions. One of them is that of Rav Yehoshua ben Karcha, who maintains that he lived in the times of Achashveirosh. His source for this is a pasuk in Iyov (42:15) which states: ולא נמצא נשים יפות כבנות איוב בכל הארץ - “Iyov’s daughters were the most beautiful women in the world”. When was there a time in world history that the entire world was searched and examined for beautiful women? In the times of Achashveirosh.
However, this explanation presented Rav Yehoshua ben Karcha with a difficulty. If Achashveirosh set up a royal beauty pageant to seek out the most beautiful woman to be his wife, why didn’t he choose one of Iyov’s daughters if the pasuk testifies that they were the most attractive women in the world at that time, and why did he choose Esther if she was less beautiful? To resolve this question, Rav Yehoshua ben Karcha concluded that Esther’s selection had nothing to do with her true appearance, as she was in fact naturally unattractive, but Hashem miraculously caused her to find favor in the eyes of everyone who saw her, which caused Achashveirosh to select her over Iyov’s daughters.