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Question:
Is it possible that we simply do not merit to have Moshiach come in our time?
Answer:
G-d will see that the Jewish people are struggling to survive and He will hasten to redeem them.
The authors of the Mishnah and Gemara divulged to us the signs of Redemption - signs that are not at all complimentary to the Jewish people. For example, the end of Mishnah at the conclusion of Sotah (49b) and the Gemara in Sanhedrin (97a) state: "In the final days before the advent of Moshiach, insolence will abound. There will be no rebuke; children will shame the elderly and the elderly will stand before youth... A man's enemies will be the members of his own household, the wisdom of the sages will become corrupt, those who fear sin will become repulsive, and truth will disappear."
How do we reconcile these passages in the Talmud with verses in the Torah that clearly promise that the redemption will occur when we all return to G-d? The verses state: "There will come a time when you will experience all the words of blessing and curse that I have presented to you... And you will return to the Lord, your G-d, and obey Him.. Then the Lord, your G-d, will return your exiles..." (Devarim 30:1-3).
The simplest explanation is that both views are correct: In the time of Redemption, there will be those who will work hard to hasten the redemption by increasing in good deeds and following G-d's commandments. There will be others whose behavior will fit the aforementioned description in the Talmud: They will reject the yoke of G-d due to the difficulties of observance. G-d will see that the Jewish people are struggling to survive and He will hasten to redeem them, before the Jewish people becomes utterly lost, G-d forbid.
(The Chofetz Chaim on Awaiting Moshiach, p. 28-33)
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