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                                                                                B"H   
Vaetchanan – When “No” Doesn’t Mean Stop Asking

There’s a fascinating and frankly baffling Midrash that tells us Moshe Rabbeinu prayed 515 times to be allowed entry into the Land of Israel. 515! And each time God responded with a definitive “no.” Most of us, after a few unanswered prayers—or maybe even one—might take the hint. But not Moshe. He keeps going, davening with intensity and sincerity, until God finally says, “Enough already. Don’t ask again.”

And here’s the question that gnaws at me: If Moshe believed with perfect faith in God—His justice, His compassion, His wisdom—why didn’t he just accept God’s decision and move on? Isn’t part of belief surrendering to the Divine Will, even when we don’t like the answer?

But maybe there’s something deeper going on here. Maybe Moshe wasn’t challenging God’s authority—he was honoring humanity’s mandate to feel. To desire. To plead. There’s a concept I like to call the “complexity of objectivity.” God, from His eternal, omniscient vantage point, may see the full picture, but we don’t. We can’t. We live in a world of shadows and nuance, where what feels right to us—through our limited human lens—may not align with the celestial calculus of the Divine.

Moshe understood that tension. He wasn’t denying God’s justice; he was expressing the pain of a man who had led a people through the wilderness, fought for their future, only to be stopped short of his dream. He prayed not to change God’s mind, but to model what it means to live with hope—even when the answer is no.

But let’s be clear: This is not some moral relativism that claims all opinions are equally valid. Far from it. Evil is evil. Antisemitism, terrorism, and hatred cannot be legitimized just because someone wraps it in nice words or parades it through the halls of the United Nations.

Take, for example, the current debate over humanitarian aid to Gaza. Some believe aid should be halted until the hostages are returned. Others argue that we must never let innocents starve, even in the fog of war. You may disagree with one or the other, but both are rooted in genuine moral concern. But the claim that Israel is to blame for Gaza’s suffering, while ignoring the barbarism of Hamas—that’s not morality. That’s moral rot.

Or look at the ever-elusive two-state solution. After October 7th, it’s perfectly reasonable to feel that a sovereign Palestinian state next door is a non-starter. Others, equally patriotic, believe a negotiated solution is the only way to safeguard our children’s future. I may not know the answer—but I do know that pressuring Israel right now, while she’s burying her dead and defending her borders, is not diplomacy. It’s betrayal. It’s the return of the oldest hatred, dressed up in the language of progress.

And yet, even as we face these challenges, we can learn something profound from Moshe’s relentless prayers. Even when God says no, we still ask. Even when the future is unclear, we still hope. That’s not denial—it’s faith. That’s not weakness—it’s resilience.

So this Shabbat, let’s be like Moshe. Let’s keep praying, keep hoping, and keep believing—in ourselves, in our people, and in the future that still lies ahead. Because even when the gates seem closed, we never stop knocking.
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And maybe, just maybe, one more prayer will be the one that opens them.
 
Rabbi Jack Engel