Shalom Tal and thank you for your question! There are many interpretations and much discussion in the Talmud as to when the Messiah will come. Before we address that, I would like to point out something important. There are many issues that are discussed in depth in the Talmud, which is the basis for the Jewish code of law. The Midrash states that there are 70 ‘faces’ (or facets,) to the Torah. How can this be? Which one is true? In a nutshell, they are all true, and come to teach us something, even when they appear to be contradictory, but that’s for a different discussion.

In your question you may have been referring to the following quote from Rabbi Yochanan in tractate Sanhedrin: “The son of David (the Messiah) will not come until the whole generation is meritorious, or blameworthy.”

The commentary of the Maharsha explains that these two states of meritorious or blameworthy, correspond to two scenarios of Redemption that are discussed in the Talmud. “Rabbi Eliezer says: The Jewish people do Teshuvah (return to G-d) – and are redeemed.” This statement corresponds to the idea of meritorious.

It means that if the Jewish people return to G-d (often mistranslated as repent) on their own initiative, they will immediately be redeemed.

Rabbi Yehoshua says that if the Jewish people do not return to G-d on their own “The Holy One Blessed be He will set over them a ruler whose decrees are as harsh as those of Haman, and then they will return…” This is the condition of blameworthy. When the Jewish people have reached rock bottom, G-d will be forced, so to speak, to bring about circumstances that will cause them to return and thus become worthy of Redemption.

Rabbi Yehuda Loewy of Prague (known as the Maharal,) explains the quote from Rabbi Yochanan on a deeper level. The era of the Messiah will be a new phenomenon in a rectified world. Therefore, the world must be made ready, and transition to the new status, and this could come about in one of the two ways mentioned. The first option would be that mankind would reach the peak of perfection possible, and thus be worthy of Redemption, or the second option, that humanity hits rock bottom, and then there’s no choice but to redeem them.

Chassidic teaching is that Redemption can come when the good has been sifted out as it were from the evil. As long as we haven’t managed to salvage all the sparks of goodness that got mixed up with evil in the world and make a clear distinction between good and evil, we cannot be redeemed. So, either the good that becomes revealed will succeed in pushing away the evil entirely, bringing the world to a state of Redemption, or the force of evil will rule and then G-d will have to eradicate the world.

If however, the generation is blameworthy, then in what merit can we be redeemed? The Talmud quotes from Isiah: “And he shall see that there is no man, and shall be astonished that no one is hurt, and his arm shall be saved.” Meaning that G-d will see that there is no merit, and will redeem us in His own merit!

Rabbi David Kimche (known as the Radak,) explains that this situation will take place at the beginning of the Redemption. “There is a possibility that (they – the generation of the Redemption,) will not return to G-d until the beginning of the Redemption can be seen.” Then, he explains, the majority will return to G-d. The Radak also maintains that there cannot be a situation where the entire generation is blameworthy, without any righteous people, worthy of being redeemed, rather, the reference is to the majority.

Our generation is considered by many to be a generation of ‘kidnapped children’, in other words, most of the generation have not received the kind of education that would encourage and inspire them to keep all the commandments and behave righteously according to what is outlined in the Torah, so that they cannot be judged for not keeping it. According to this approach, it is actually considered a righteous generation.