October 11, 2025
Author(s): Rabbi Wes Gardenswartz,
Shabbat Chol Ha’Moed Sukkot
Dare to Be Hopeful, or Cautiously Pessimistic?
October 11, 2025 – 19 Tishri 5786
Temple Emanuel, Newton, MA
Obviously, there is only one thing to talk about. Please God in the next few days the twenty Israeli hostages still held by Hamas in Gaza are to be released as part of phase one of the deal brokered by President Trump, his team, and a host of nations. More than two years after they were taken hostage, these twenty surviving hostages who have been in hell for an eternity will at long last be home, reunited with their families. And the question is, how do we process this monumental and joyful event?
Donniel Hartman and Yossi Klein Halevi offered two different lenses in a recent For Heaven’s Sake podcast when President Trump’s 20-point plan was first announced.
Donniel observed that the whole point of the Jewish high holiday season is that we are not stuck. What has been does not necessarily shape what could be. Our past need not shape our future. We can evolve. We can grow. We can change. The past two years have obviously been beyond horrific. But Donniel asks: Dare we be hopeful again?
Yossi offered that he would love to be hopeful. And before October 7 Israelis famously scored very high on happiness tests. But in the two years since October 7, it is all too common for Israelis to feel, as Yossi put it, “cautiously pessimistic.” That is a new thing, but it is real, and well earned.
So what lens better fits this moment: daring to be hopeful or cautiously pessimistic? The evidence cuts both ways.
The return of the hostages is the deepest joy. Their return invites us to dare to be hopeful. After all, for more than two years, those 20 hostages never gave up; and their families never gave up. The Jewish world never gave up. Activists especially in Israel, protesters in hostage square, never gave up. They made the issue of bringing the hostages home front and center every day for two years. The fact that this unrelenting hope in unremitting darkness will finally yield freedom and family reunion and life and love is the very embodiment of joy. Dare to hope that the long, excruciating, national nightmare is finally over. Dare to hope that after two years of being stuck in October 7, Israel can finally, finally begin to heal from the trauma of that day.
And yet, Yossi’s lens also resonates. There are several significant reasons to be cautiously pessimistic despite the intense joy of twenty living hostages coming home.
There are the twenty-eight hostages who were murdered on October 7 and in Gaza whose remains have to be located and returned to Israel for proper burials.
There are approximately 2,000 Palestinian terrorists that Israel has to give up in order to get the 20 living Israeli hostages. We all know that the architect of October 7, Yahya Sinwar, was released from an Israeli jail in the deal for Gilad Shalit. The question of what price future Israelis will pay as a result of the release of these 2,000 prisoners is real, and it hangs over the horizon like a storm cloud.
And there is the cost paid by IDF soldiers and their families. Wednesday night Dan Senor did an emergency edition on his Call Me Back podcast with Israeli journalist Nadav Eyal who pointed out that 466 IDF soldiers have fallen in battle in Gaza. Eyal then did the horrible math. He observed that more than 20 IDF soldiers died for every hostage who is to be returned, which shows that they died fighting for a moral cause—securing the freedom of kidnapped civilians—and it shows the State of Israel’s ironclad commitment to protect its citizens. But the tragedy of these 466 beautiful lives cut short, and their grief-stricken families, is also part of the weight of this very complicated moment.
All these imponderables connect to phase one of the deal. As to phase two, there are also serious questions that have no ready answers. What will be with Hamas’s arms? Will they really give up their arms? Their new language is that they will “freeze” their arms. Nobody knows what that means. And if there is some international peacekeeping force in Gaza, what will happen when Israel learns that Hamas is rearming if the international force does not stop it? As Nadav Eyal pointed out, nobody has the answers to these very important questions.
So what is your lens: daring to be hopeful or cautiously pessimistic?
For me, the crucial teaching in our canon is the prayer we say every morning. We bless God, barchu et Adonai hamevorach, blessed be God who is blessed, and then we say about God: yotzer or u’voreh choshech, God creates light and darkness. Light and darkness are always present in every picture, and our prayer life trains us to try to find a way to praise God in the midst of that very contradiction.
The soul I want to have is the soul of Danny Gordis’s burly Israeli mechanic who works for the Toyota dealership in Jerusalem. Danny recently wrote a column about his and his wife Elisheva’s extra car. One day his son asked if he could use the car to drive back and forth to miluim, reserve duty. Danny and Elisheva were happy to give their son the reservist their extra car.
When he was done, he asked his parents if his friend, who also has miluim, could use the car. Sure, Danny and Elisheva said. And so it went. The car became the miluim car. A succession of reservists used the car to get to and from their service.
One day, the reservist who was using the car saw the dreaded icon light up on the dashboard. There was some problem with the car. The reservist called Danny, and told him about the problem. Danny told the reservist take the car to my mechanic.
The shop calls Danny and says: it will cost a significant amount to fix it. Danny knew it did not make sense as an economic decision, but he liked the car being used to help reservists, so he authorized the work. The shop calls back again. I made a mistake. It’s going to be twice my initial estimate. Danny meets with the mechanic, and they agree that Danny will sell the car for a nominal amount for parts. When Danny explained that the car had been used for years by reservists, this Israeli mechanic reacts:
This giant, burly guy in the black, two-button Toyota shirt sits there, looks at me, and his eyes well up with tears…
I got up to go, shoved the little bit of paperwork into my bag, and started to walk. Come here, he said.
He came out from behind his desk and towering above me, gave me a big hug.
Yihye be-seder po, he said. Things are going to be OK here.
Nekaveh, I said. Let’s hope so.
He released me from the bear hug, patted me on the shoulder, and—still bewildered by my little story—shook his head and said, “Shana Tova.”
“You, too.”
I walked home, charmed by the bear of a guy and those utterly unexpected tears.
The whole thing was so incongruous, that moment so filled with his sweetness and goodness, that—knowing that this country is filled with people like him—it struck me that he might well be right.
Dare to be hopeful, or cautiously pessimistic? Personally, I am going to dare to be hopeful because I believe in the goodness, decency, integrity, strength, idealism, nobility, and beauty of the Israeli people, soon to be strengthened by twenty hostages who, against all odds, separated from home and hope, dared to be hopeful. What they dared to dream is coming true. Maybe, just maybe, the message of the High Holidays is actually true: we are not stuck. Let’s hope so. Shabbat shalom.