Book Five

Midrash Eicha (1:1) describes three leaders that said the איכה throughout Jewish history.  The first is Moshe in our parsha, אֵיכָ֥ה אֶשָּׂ֖א לְבַדִּ֑י טׇרְחֲכֶ֥ם וּמַֽשַּׂאֲכֶ֖ם וְרִֽיבְכֶֽם.  The second is Yeshiyah (in the haftorah,) אֵיכָה֙ הָיְתָ֣ה לְזוֹנָ֔ה קִרְיָ֖ה נֶאֱמָנָ֑ה מְלֵֽאֲתִ֣י מִשְׁפָּ֗ט צֶ֛דֶק יָלִ֥ין בָּ֖הּ וְעַתָּ֥ה מְרַצְּחִֽים.  The third is Yermiyahu (Eicha 1:1) אֵיכָ֣ה׀ יָשְׁבָ֣ה בָדָ֗ד הָעִיר֙ רַבָּ֣תִי עָ֔ם הָיְתָ֖ה כְּאַלְמָנָ֑ה רַבָּ֣תִי בַגּוֹיִ֗ם שָׂרָ֙תִי֙ בַּמְּדִינ֔וֹת הָיְתָ֖ה לָמַֽס.  The midrash gives a parable contrast the three mentions of eicha. There was a noble woman who was observed by three close friends: one saw her in successful times; one saw her in her "haste;" one saw her in her disgrace. So too, Moshe asked eicha during the time of Bnei Yisrael’s honor. Yeshaya asked it in their struggles. Yirmiya used it in their disgrace.  

The Tikkunay Zohar #69 (pg. 110b) says the word איכה is made up from the words 'איך ה - how did the 'ה fall.  When Adam sinned he was rebelling against the malchus of Hashem, represented by the letter hey.  The hey fell.  It is the same reaction throughout all the tries and tribulations of Klal Yisroel that lead to all the tragedies.  How could it be that there is such a lack of recognition in the malchus of Hashem?

That is what Hashem asked Adam, וַיִּקְרָ֛א י״י֥ אֱלֹהִ֖ים אֶל־הָֽאָדָ֑ם וַיֹּ֥אמֶר ל֖וֹ אַיֶּֽכָּה.  How did you create this פגם in the 'ה.  

It is our job to fix this hey,  Rav Tzaddok cites the following amazing story of Rav Zusha.

That is why we enter 9 Av going into the fifth Book of the Torah.  It is to remind us what is our job to fix on this sad day.  (It is also noteworthy that this week was the yom hilulah of the Arizal on the 5^th day of the 5^th month, 5 Av.)