When will the Messiah come? According to Sanhedrin 97a, the Talmud presents a seven-year countdown—and then immediately undermines it.
The Sages taught: in the Sabbatical cycle during which the son of David arrives, the first year brings selective drought. The second brings arrows of famine. The third brings a great famine—men, women, children, and the pious die, and the Torah is forgotten. The fourth brings partial recovery. The fifth brings abundance and rejoicing. The sixth brings heavenly voices. The seventh brings wars. And in the year after the Sabbatical cycle, the Messiah comes.
Rav Yosef immediately objected: many Sabbatical cycles have passed with these patterns, and the Messiah has not come. Abaye countered: have all these phenomena actually occurred in the correct order? Heavenly voices in the sixth year? Wars in the seventh? The sequence has never been completed.
Rabbi Yehuda described the generation in which the Messiah arrives: the Galilee will be destroyed, the scholars' assembly hall will become a place for prostitution, wisdom will rot, piety will be despised. "The face of the generation will be like the face of a dog"—shameless, driven by appetite. Truth will scatter like flocks wandering in different directions.
And then the Talmud delivers its most radical teaching on the subject. Three rabbis—Rav, Shmuel, and Rabbi Yohanan—all agreed: let the Messiah come, but let me not see him. The suffering that precedes redemption is so terrible that even the greatest Sages preferred to die before its arrival.
The passage also records a mysterious tradition: the Messiah will come only in a generation that is either entirely righteous or entirely wicked. The proof text is (Isaiah 59:16): "And He saw that there was no man, and was astonished that there was no intercessor; therefore His own arm brought Him salvation." Redemption arrives at the extremes—never in the comfortable middle.