The Medrash (Eicha Rabba 1:1) tells us that three people used the word Eicha. Moshe Rabbeinu, Yeshaya, and Yirmiya. Moshe Rabbeinu asked in Devarim (1:12), “Eicha Esa Livadi; How can I alone, carry the nation? " The Medrash contrasts these three quotes, in that Moshe used it in the time of Am Yisrael’s glory, Yeshaya in the time of their distress, and Yirmiya during our low point and our utter disgrace.
Rav Moshe Feinstein in Darash Moshe says that although they all used the word at different levels of Am Yisrael’s status in the world, all three meant the same thing. They all pointed out Am Yisrael’s weak point and the reason for our downfall. Yes, Moshe Rabbeinu said it during our glory days, but he was referring to the invisible flaws that he saw, which were capable of opening into large craters as they did in the time of Yeshaya which later proved to become unbridgeable gaps that led us into the abyss in the times of Yirmiya.
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