The Malbim writes that Esther’s two conditions refer to separate factors. The first, “seeing evil” refers to possible anti-Jewish attacks before the decree date. The second, “seeing the destruction” refers to people perhaps not believing the second (erstwhile unmentioned) document, and attacking the Jews nevertheless.
In Nachal Eshkol, the Chida explains that Esther is telling the king that – having not been present during the meeting that spawned Haman’s decree – she does not know if, by using the term li’avdam (Esther 3:9), Achashverosh meant to enslave or kill the Jews. On that basis, can’t bear evil (enslavement) nor the destruction (killing) of the Jews.
The Vilna Gaon notes that the verse uses the word, eicha (“how”) twice – once for the first Beis HaMikdash, and the second for the second Beis HaMikdash. Indeed, Esther was mourning for two things – the potential destruction of the Jews in exile from the first Beis HaMikdash, and the inevitable destruction of the Jews of the future if they do not learn from their past mistakes.
Contrary to the previous opinions, the Yosef Lekach writes that Esther is not worried the people will be destroyed. After all, H-Shem already promised never to kill them out (Vayikra 26:44). However, there was no such promise about individual families, and that was a cause of concern for Esther. The Jewish people would survive, but Esther’s second eicha indicates that she worries about her future progeny surviving.
Perhaps she had good reason to worry, since Mordechai had threatened her offspring with as much when he convinced her to approach the king (Esther 4:14), and it is a well-known Talmudic (Kesubos 103b) dictum that what the righteous speak, H-Shem fulfills.
The Beis HaLevi (on his commentary to Ki Sisa) writes that by using “my nation,” Esther refers to those who would not renounce their Judaism if that is what Achashverosh is planning to do. By saying “my kin,” Esther refers to those people who would (chas v’shalom) give up their Judaism to save their lives.
R’ Moshe David Valle writes that Achashverosh seems surprised by the decree he permitted less than a week earlier simply because H-Shem created forgetfulness (see the Dubno Maggid’s explanation of Devarim 32:18). Being able to forget can sometimes be a blessing.
Similarly, R’ Yehonason Eibshutz says it was the king’s foolishness that caused him to forget. Accordingly, this is another root of the custom to drink ad d’lo yada on Purim (Megillah 7b).
The Beis HaLevi writes that Achashverosh did not know that the decree was meant to destroy the Jews, but thought it was supposed to only assimilate them. After all, the word l’avdam could mean “cause them to be lost.” This is why Haman emphasized the Jews’ strangeness (Esther 3:8-9). The solution for “fixing” a group of people who are “weird” is to acculturate them into society. Also, this is the reason Haman said (Esther 3:11) “la’asot bo” (“to do with”) rather than “la’asot lo” (“to do to”) the Jews. This implied that if the Jews refused, they would be punished, but the punishment was not the focus. However, in the decree he wrote (Esther 3:13), Haman emphasized the punishment. This is why Esther (Esther 7:4) first notes this punishment in her plea to the king.
The Ohel Moshe quotes the Be’er Yosef that there was a fundamental difference between Haman and Achashverosh – Haman knew that the king was only interested in having the Jews conform to his society’s norms, but he likewise knew that the Jews would sacrifice their lives to avoid conversion. For many Jews, an order to change was a death sentence for the Jews. This is the way he put on a show that left Achashverosh in a state of confusion.
R’ Avraham Yehoshua Heshel (the Apter Rav) tells a story about the time of R’ Sherira Gaon (father of R’ Hai Gaon) of Pumbedisa (906-1006 CE). There were two brothers fighting over their late father’s estate. One got a Torah scroll actually written by Ezra the Scribe, while the other brother got everything else in the estate. Parenthetically, it is a beautiful thing that the one who got all of the father’s possessions would be willing to give them up for a Torah scroll. Be that as it may, one evil man who thought it was ridiculous that the brothers were fighting over what he considered nothing more that a large parchment with ink on it, came into shul at night and scratched out the letter ayin in the word vi’avadetem (“and you shall serve”) in the verse (Shemos 23:25), and wrote an aleph in its place, turning the word into vi’avadetem (“and He will destroy you”). When this change was discovered, the owner of the scroll fell ill. He then had a dream in which his father appeared. His father told him the culprit will lose his eye because of the verse (Shemos 21:24) “ayin tachat ayin” (“an eye for an eye”) can be homiletically interpreted as an eye in place of a letter ayin. Since the scroll’s owner was concerned lest another scribe fix a scroll written by Ezra, the father calmed him by saying that Ezra in Heaven would fix it. Indeed, the next morning, the recovered owner came to shul, and together with the congregation was astounded to find the scroll in its original form. The Apter Rav brings this story as proof that Achashverosh really wanted the Jews to be subservient to him, but Haman used the word li’avdem to intentionally mislead the king into signing a decree to kill them all.
According to the Yerushalmi, Esther phrases her question as “what is this and why is this” to demonstrate that she was asking two questions: a) what was the meaning of weeping and b) what was Mordechai’s justification for rejecting the royal clothes she had sent.
Yosef Lekach writes that Esther’s phraseology likens her to a doctor, who diagnoses both the illness and then figures out the cause. Here, also, “what is this” refers to Mordechai’s seemingly strange behavior, and “why is this” refers to the root cause of his concern.
The Ohel Moshe points out that this verse demonstrates just how a great person deals with any tragedy. In any such situation, the great person will seek the spiritual cause, since the spiritual is the actual, whereas the physical/political/personal causes are but a mere reflection in this impermanent, transient mirror to the spiritual world.
The Midrash (Esther Rabbah 8:4) and the Talmud (Megillah 15a) both relate that Esther’s question to Mordechai of two mentions of the word, “zeh” concerned whether or not the Jews transgressed the laws of Moshe’s tablets, which are similarly described as “m’zeh l’zeh” (“from one side to the other”) (Shemos 32:15). R’ Dovid Feinstein explains that Esther was concerned with Torah at this time because she recognized in the gravity of situation that the only cause could be a failure in the Jews’ commitment to the Torah. Interestingly, the Torah was written “mzeh l’zeh” so that each letter could be seen from either side of the tablets. The reason for this, according to Rabbeinu Bachya’s commentary there, is to symbolize the hidden and revealed Torah. Perhaps we can also say that these are the Written and Oral parts of the Torah.
The Midrash (Esther Rabbah 8:4) writes that Esther’s “zeh” question concerned the Jews’ neglecting the responsibilities to which they committed themselves at the splitting of the sea, regarding which is written “zeh Keili vi’anveihu” (“this is my G-d and I will glorify Him”) (Shemos 15:2). The Beis Halevi there explains that both instances of “zeh” precipitated in Amalek’s attack of the Jews in the desert. In other words, the Jewish peoples’ disregard for Torah study and their lack of trust in H-Shem brought Amalek in the desert – and brought their descendant, Haman, in Persia generations later for the same behaviors.
In his unique manner, the Ben Ish Chai focuses on Esther’s use of the word “ma” (“what”). He points out that the letters immediately preceding the mem and hey of “ma” are lamed and dales and the letters immediately after mem and hey are nun and vuv. Together, these four letters spell out “nolad” (“a new creation”). The Ben Ish Chai therefore notes that Esther wanted to know if the Jews were being punished for the previously-mentioned pseudo-idolatry in the time of Nevuchadnetzer or attending Achashverosh’s feast, or perhaps for a newly created reason, altogether.