Our Gemara on amud aleph discusses one of the reasons why the 15th of Av became a traditional day of rejoicing, drawing from the experience of the Jews in the wilderness. After the sin of the spies, it was decreed that the entire generation would wander for 40 years and die out before entering the land of Israel. Eichah Rabbah (Pesicha) offers a poignant description of how the 15th of Av marked a turning point in their fate:
Rabbi Avin and Rabbi Yoḥanan said: The 15th of Av was the day when the dying in the wilderness ceased. Rabbi Levi explained: Every eve of the ninth of Av, Moses would instruct the camp, "Go out and dig," and they would go out, dig graves, and sleep in them. In the morning, Moses would announce, "Rise and separate the dead from the living," and they would stand up and take out those who had passed away. Each year, 15,000 or more would die until the total of 600,000 had perished over the 40 years. However, in the 40th year, when they went into their graves, no one died the next morning. Assuming they had miscalculated, they repeated this process on the tenth, the eleventh, the twelfth, the thirteenth, and the fourteenth of Av. When the full moon appeared, they realized that the decree had been lifted, and they proclaimed the 15th of Av a day of celebration.
Rashbam and Rabbeinu Tam explain various legal distinctions in this narrative, suggesting how the final 15,000 were somehow spared. In the end, it wasn’t just Kalev and Yehoshua who survived to enter the land of Israel, but a larger group from that final year. God’s decree was mercifully rescinded in the last year. But why?
Sefer Daf al Daf suggests an answer based on human nature. People tend to avoid facing uncomfortable truths until the last moment. Each year in the wilderness, a typical person from that generation might enter his grave with the thought, “I won’t be the one to die. I am more righteous, my neighbor will be the one.” But in that final year, everyone who entered their grave had no more illusions—this time, they truly believed their luck had run out. Paradoxically, it was this stark realization that led to their full repentance, and that repentance merited a special reprieve from God.
This reflects a broader psychological truth about repentance. We hedge and bargain with ourselves, thinking that the worst won’t happen to us. Only when we reach our darkest moments are all rationalizations stripped away, leading to genuine repentance. This idea is echoed in the Pri Tzadik (Rosh Chodesh Adar 5:1). The Gemara (Yoma 54b) relates that when the gentiles captured the Temple Mount and entered the Holy of Holies, they saw the Cherubs in an intimate embrace and mocked the Jews for having such an "obscene" image in their holiest place. If the Cherubs turn away from each other when God is displeased, why were they embracing at this moment of destruction? The Pri Tzadik explains that the Jews were in denial that God would truly punish them and allow their defeat, so they did not repent. However, when the gentiles invaded, and the Jews saw that the threat was real, they began to repent. At that moment, despite the inevitability of destruction, God was pleased with their repentance.
This aligns with the famous verse from Psalm 121:1:
“I turn my eyes to the mountains; from where (me-ayin) will my help come?”
The word me-ayin can also mean “from nothing.” The Noam Elimelech (Devarim 3) explains that initially, a person looks to the “mountains”— to merit, strength, or external sources of salvation. But ultimately, one must realize that there is nothing and no one to rely on but God. Only when we acknowledge our utter vulnerability can we find true salvation.
This idea, of hitting rock bottom to find redemption, reminds us that at our darkest moments, when all illusions are shattered, we have the opportunity for real repentance and transformation.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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