A Conversation I Needed and Couldn’t Have

On Tisha B’Av, we mourn not just the destruction of the Temple, but the sinat chinam—baseless hatred—that our sages say caused it. This year, our community’s fractures seem to only grow, that ancient warning feels more urgent than ever.

I was scrolling through my phone when something clicked. It was just another piece in the endless stream of Jewish responses to Jewish positions since October 7th, but suddenly I could see the pattern I’d been missing.

We weren’t really arguing about Mamdani, or Gaza, or hostages, or humanitarian aid anymore. We were arguing about who gets to speak authentically as Jews.

The specific piece didn’t matter—I’d seen versions of this conversation dozens of times. Someone takes a position based on their understanding of Jewish scholarship or values, and instead of engaging the substance, the response focuses on their Jewish legitimacy. Are they real rabbis? Do they understand their obligations? Are they betraying their people?

When did Jewish discourse become less about wrestling with impossible moral questions and more about establishing religious authority? When did reaching different conclusions become grounds for questioning someone’s Jewish authenticity?

I suspect some who read this will challenge my approach in what follows—questioning whether I have the right to speak for these historical figures, whether my interpretations are accurate, or whether this entire exercise is presumptuous.

They might be right, but they’ll also be proving exactly the point I’m trying to make: we’ve become so focused on policing who gets to speak and how they speak that we’ve forgotten how to engage with the substance of what’s being said.

Since October 7th, I’ve watched something break that I suppose I also knew but didn’t want to accept: our ability to disagree Jewishly. Jews arguing about whether Palestinian children in Gaza are actually starving, not whether Israel should send more aid, but whether the hunger is real or staged. People I’ve been in community with for years, calling each other traitors over humanitarian assistance. Fifty souls still underground, some alive, some not, while Jewish friends destroy relationships over whether bringing them home justifies any cost.

Everyone claims Torah authority. Rabbis of all denominations, leaders, politicians, American Jewish organizations, philanthropists—all reaching opposite conclusions using the same sacred sources. All certain they speak for authentic Jewish values. Meanwhile, I’m just trying to figure out how to have a conversation that doesn’t end in excommunication.

What does amcha mean when we can’t agree on basic questions about starving children? What does Jewish peoplehood mean when our interpretations of pikuach nefesh lead us to completely different moral conclusions? On Tisha B’Av, as we read about Jerusalem’s destruction caused by internal hatred, these questions feel especially pressing.

Most of my public comments since October 7th have focused on the hostages, in part because of personal connections, but also because it’s the one thing I can say without betraying people I love who are suffering. I know people whose children are in the IDF. I know hostage families. But that reality has also left me feeling voiceless on so many of the deeper questions that keep me awake.

I couldn’t find anyone speaking with the kind of moral authority I was looking for—voices grounded in deep knowledge and earned through real sacrifice, not just recently developed strong opinions.

So I tried something that might sound strange: I’ve been using AI extensively in my work, and it occurred to me that this might be an opportunity to engage with past leaders whose wisdom seems absent from our current discourse.

I arranged an imagined conversation working through what each of these thinkers would contribute based on their actual lives and intellectual frameworks.

Maybe it’s presumptuous, but I needed it.

Elie Wiesel, who spent 60 years wrestling with what Jewish ethics mean after the world’s silence during genocide. I needed Golda Meir, who lived through the intelligence failures of 1973 and understood the weight of impossible decisions. I needed David Ben-Gurion, who believed Jewish sovereignty was meaningless without Jewish ideals. I needed Maimonides, the refugee physician who wrote systematically about when it’s permitted to take life while saving it. I needed Hannah Arendt, who understood how communities maintain moral coherence during crisis. And I needed Rabbi Jonathan Sacks, who tried to bridge traditional Judaism with contemporary moral challenges.

Zichronam livracha” (זכרונם לברכה) — “may their memories be for a blessing.”

On Jewish Moral Authority

When I asked them about the breakdown of Jewish moral discourse, Maimonides responded with characteristic precision: “What you describe is the confusion of institutional position with intellectual authority. True da’at Torah—authentic Jewish knowledge—emerges from rigorous engagement with sources, systematic reasoning, and above all, intellectual humility about what we cannot know. When I fled Córdoba, I saw scholars use religious authority to avoid hard questions rather than engage them.”

Hannah Arendt pushed deeper: “What you’re witnessing isn’t just confused authority—it’s the breakdown of what I called ‘the space of appearance,’ the public realm where people can act and speak as equals despite their differences. When communities face existential pressure, they retreat into conformity rather than genuine political discourse. People stop thinking and start performing predetermined roles.”

Wiesel brought it back to lived experience: “After the war, I watched how Holocaust memory became weaponized by people who never lived through it. Authority based on proximity to trauma can be just as corrupted as authority based on institutional position. The question isn’t who has the right to speak, but whether they’re speaking from genuine wrestling or from the false certainty that comes from never having one’s faith truly tested.”

I found myself thinking: if even Wiesel worried about people weaponizing trauma for authority, what hope do the rest of us have?

On Starving Children and Jewish Identity

When I confessed my anguish about hungry children in Gaza and how looking away makes me feel less Jewish and less human, Ben-Gurion challenged me directly: “You feel less Jewish when you look away from hungry children because you understand something our current leaders have forgotten: Judaism isn’t just about Jewish survival, it’s about what kind of people we become through surviving. When we declared independence, we promised to build a society based on ‘freedom, justice, and peace’—not because the world demanded it, but because we understood that Jewish sovereignty without Jewish values would be a hollow victory.”

Wiesel was even more direct: “Jewish suffering doesn’t exempt us from Jewish obligations. If we use our trauma to justify ignoring other people’s children, then we have learned nothing from our own children’s deaths. The Shoah taught me that indifference is the greatest sin. Not just indifference to Jewish suffering, but indifference to suffering itself.”

But Golda forced me to confront the brutal realities I’d been trying to avoid: “Yes, those children in Gaza are hungry. Yes, Hamas steals aid to build tunnels and rockets. Yes, every bag of flour we send might be used to kill Jewish children tomorrow. All of these truths exist simultaneously, and anyone who tells you otherwise is either lying or hasn’t carried the burden of Jewish survival. The mistake is thinking that acknowledging Palestinian suffering means you care less about Jewish suffering.”

Maimonides brought his systematic reasoning to bear: “The question about Gaza isn’t whether Palestinian children deserve food. The answer is obviously yes. The question is whether providing that food, under current circumstances, increases or decreases the overall preservation of life. This requires calculation, not sentiment. But the calculation must include the full range of consequences, including what happens to Jewish souls when we become indifferent to non-Jewish suffering.”

None of this made me feel better about my paralysis, but at least I wasn’t alone in finding it impossible.

On the Hostages and Impossible Choices

The hostages produced the most anguished responses. Wiesel spoke from the deepest places: “In the camps, we lived on the hope that someone, somewhere, would say: ‘These lives matter more than strategy.’ The hostage families are asking us to be that person for their loved ones. But I also saw how the world’s silence taught our enemies that Jewish lives were expendable. There is no clean answer. There is only the recognition that some choices leave moral stains that never wash clean, and the obligation to choose anyway.”

Rabbi Sacks provided the ethical framework: “You’ve identified the hardest question in Jewish ethics: what happens when our highest values conflict with each other? The tradition acknowledges that in such cases, we cannot achieve moral purity. We can only choose the path that best honors the totality of our obligations while mourning what we sacrifice.”

Maimonides was characteristically precise: “The obligation of pidyon shvuyim—redeeming captives—is indeed among the highest mitzvot, and the Mishnah explicitly teaches that ‘we do not redeem captives for more than their worth’, not because lives lack infinite value, but because overpaying encourages more kidnapping. This calculation must be made with full awareness of its moral cost, with genuine anguish at the lives it fails to save.”

Hearing Maimonides acknowledge the anguish made me feel slightly less pathetic about my own inability to find clean answers.

A Path Forward: Learning from Our History of Destruction

What emerged from this conversation wasn’t answers, which is probably good, since this was an AI hallucination, and I’m not qualified to provide those anyway. Instead, I found a way of thinking about impossible questions that honors their complexity.

Rabbi Sacks reminded me of what we’ve lost: “We’ve inherited a tradition of machloket l’shem shamayim—argument for the sake of heaven—but we’ve forgotten that this requires recognizing our opponents as fellow servants of the same ultimate truth. The Talmud preserves the disputes between Hillel and Shammai not because they agreed, but because they disagreed constructively while remaining committed to shared destiny.”

When Jewish leaders start excommunicating rather than engaging, they’ve abandoned the very process that makes Jewish reasoning Jewish. The Talmud preserves minority opinions not because all positions are equal, but because moral truth emerges through sustained engagement with opposing views.

The problem isn’t that we disagree about Gaza or hostages or humanitarian aid. The problem is that we’ve lost the ability to disagree Jewishly, at least publicly. On Tisha B’Av, this failure takes on urgent meaning. Our sages taught that the Second Temple fell not because of external enemies, but because of sinat chinam—the baseless hatred that destroyed our capacity for sacred argument.

I’m not pretending to have solutions. But there’s hope in what these voices taught me. We can restore Jewish moral discourse, though it requires commitments that feel especially relevant as we observe this day of mourning and reflection:

First, we must distinguish between engaging in arguments and policing authenticity. Intellectual authority comes from rigorous engagement with sources and intellectual humility, not from institutional position or even simply the proximity to suffering.

Second, we must create spaces for genuine wrestling. Communities under threat retreat into conformity. We need to actively preserve spaces where Jews can think together about unprecedented questions without being reduced to their positions.

Third, we must hold complexity without collapsing into false certainties. Jewish leadership means carrying the full weight of impossible choices, not pretending they have clean solutions.

Fourth, we must ground our moral reasoning in Jewish sources while acknowledging their complexity. We must speak from genuine wrestling, not false certainty.

Finally, we must remember that Jewish sovereignty creates obligations, not exemptions. The question isn’t just whether we survive, but what kind of people we become through surviving.

This isn’t a call for false unity or moral relativism. It’s a personal prayer and a hope to restore the kind of Jewish moral reasoning that can navigate genuine tragedy without fracturing into warring camps. To remain recognizably Jewish in a complex world, we cannot afford to accept anything less.

This was an interesting AI rabbit hole, and the conversation I needed couldn’t happen in reality. Even so, the principles and wisdom the conversation revealed have tilted me back to the kind of grounding Judaism that inspires my personal and professional commitment to this complicated religion and community.

On Tisha B’Av, as I mourn what we’ve lost, I hope to also commit to rebuilding what’s broken and in our capacity to remain one people capable of sacred argument rather than destructive hatred.