Ask Haviv Anything – Episode 44: Fateful Choices to Make in the New Year, a Comment for Rosh Hashanah

Host: Haviv Rettig Gur
Date: September 22, 2025

Overview

In this contemplative Rosh Hashanah episode, Haviv Rettig Gur meditates on the Jewish New Year’s deeper meanings, connecting its themes of darkness, renewal, and the possibility of radical pivots to the current tumultuous moment for Israel, the Jewish people, and the broader Middle East. He weaves together tradition and history with Israel’s contemporary challenges—war, antisemitism, geopolitics—urging listeners to grapple with choices and agency in an uncertain year.

Key Discussion Points & Insights

The Significance of Rosh Hashanah: Darkness, Pivots, and Renewal

• Haviv reflects on returning home for Rosh Hashanah amidst personal and national disruption, noting the holiday’s symbolism:

  “Rosh Hashanah is the only Jewish holiday that falls on a moonless night…in a world before electricity, that’s the moment of blackest darkness.” (06:02)

• The holiday, he asserts, “is a day of tremendous pivots,” referencing Jewish tradition:

  • Joseph’s release from prison,
  • Abraham’s binding of Isaac (and the last-minute substitution with the ram),
  • The creation of humanity—each representing moments of existential change.

• The shofar, or ram’s horn, is central—meant to “awaken us to repentance and to awe” (09:37):

  “The cry that the Torah says is the heart of this day is meant to jar us, to startle us, to make us look around, to see that there’s always a ram in the thicket, or there’s always an alternate path…It is never not a moment for pivoting, for questioning, for noticing that alternatives were built into creation itself.” (12:06)

The State of the Jewish World & Israel at the Cusp of the New Year

• Haviv sets the current tone:

  "A year that is going to be a year of war, a year of disruption, a year of antisemitism, a year of suffering of civilians, a year of a lot of unanswered questions…” (02:40)

• He observes a “diplomatic storm” over international recognition of a Palestinian state, highlighting moves by Britain, France, Australia, Portugal, and others. (21:24)
• Haviv analyzes how these recognitions play domestically and internationally, focusing on their real-world impact rather than their symbolic value.

The Hamas Dilemma & “Order of Operations” in Peace

• He explains that the world’s pressure is misplaced unless it actually addresses the core obstacle—Hamas’s role and ideology:

  “The question…isn’t whether the recognition of a Palestinian state is a good or a bad thing…It is which Palestinian state you’re recognizing, what comes of it, what will actually be its practical effect.” (22:02)

• Recognition, he contends, currently incentivizes both sides to continue conflict; Hamas claims victory, Israel is unmoved.
• Western leaders (e.g., Starmer, Macron) advocate for a future Palestinian state “without Hamas,” but Haviv is skeptical:

  “As if Starmer has any say. As if Hamas doesn’t make that decision. It’s deeply foolish.” (26:00)

• He urges an “order of operations”: defeat Hamas first, then pressure Israelis, otherwise “you neutralize your own pressure on the Israelis.” (31:36)

Notable Quote

“There’s an order of operations here. Most people get that, left and right out there in the West…that you must first remove Hamas. When it is no longer reasonable for Israelis to think that everything Palestinian is an argument for their own destruction, then you swing around the pressure on the Israelis.” (32:20)

Challenges in Israeli Public Diplomacy (Hasbara)

• Haviv laments Israel’s lack of effective global narrative or “information war” strategy:
  • New ambassadors lack strong English or media aptitude.
  • Israel fails to engage Western publics, especially those open to nuanced arguments.

  “Israel has no interest, no capacity to even imagine what an information war policy would look like.” (41:40)

• The result: Israel’s case is lost by default, and international discourse is shaped without its participation.

Geopolitical Underpinnings: Egypt and Syria

• Egypt:
  • Massive Sinai militarization, building missile silos, “in complete violation of the Israeli-Egyptian peace treaty.” (48:12)
  • Signs of a state in crisis, turning to monumental building as a symptom of weakening regimes.
• Syria:
  • Asad’s rare trip to the UN General Assembly signals a new openness.

  “It is a Syria that wants to build itself anew into a new and different country.” (52:30)

• Haviv comments on directions: Egypt is facing away from Israel, Syria might be facing towards – not out of love, but pragmatism.

Notable Quote

“It’s not about where you stand, it’s about which way you’re facing, which way you’re headed.” (54:21, Chabad rabbi anecdote)

Ground Realities & Grassroots Potentials in Gaza

• Bottom-up anti-Hamas enclaves are emerging, led by figures like Hussam al-Hastal in Khan Younis:

  • He gave an interview in Hebrew to Israeli TV, stating:

    "Hamas and Khan Yunis are incredibly weak, shattered... Lots of Gazans aren’t Hamas. There are many kids, they need to live and grow up without war." (58:38)

  • Points out economic realities: Gaza still uses the Israeli shekel due to lack of alternatives.

• Haviv sees potential in these organic, clan-based enfranchisements and argues Israel should facilitate a “day after” policy and communicate it both domestically and internationally.

Zionism & Agency

• Zionism, at root, is about shaping Jewish destiny through collective action:

  “It is by the hands of the Jews that the Jews' future will be decided. We must do the wise thing, we must choose the wise direction.” (01:07:13)

• He urges Israel to articulate a vision for Gaza and insists that only a fundamental change in Palestinian society will make a solution possible.

The Deeper Meaning of Creation and Time

• Drawing on Jewish philosophy, Haviv explains that creation isn’t a one-time event but a continuous process:

  “Who in his goodness every day renews the act of creation.” (01:12:19)

• The “precious gift” is time itself; every moment is new, every beginning a chance to choose differently.
• Rosh Hashanah’s message, then, is about never being truly stuck—the possibility of new paths is “embedded in creation itself” (01:18:12), and wisdom lies in finding and choosing them.

Memorable Quotes

• On the Shofar and Alternatives:

  “The ram’s horn…is meant to awaken us to repentance and to awe…There’s always a ram in the thicket, or there’s always an alternate path…”
  — Haviv Rettig Gur, (12:06)

• On International Recognition:

  “It’s not about whether the recognition of a Palestinian state is good or bad. It’s about which Palestine and what it would actually produce.”
  — (22:20)

• On the Order of Operations:

  “If you try and put the pressure on the Israelis, you build up Hamas and you neutralize your own pressure on the Israelis.”
  — (31:36)

• On Israel’s Narrative:

  “Telling the story—the Allies’ own story in Germany in World War II…The point was that Germany could be rebuilt after denazification and Gaza can be rebuilt after denazification.”
  — (46:04)

• On Agency & Direction:

  “It’s not about where you stand, it’s about which way you’re facing, which way you’re headed.”
  — (54:21)

• On Creation and Rosh Hashanah:

  “Who in his goodness every day renews the act of creation…the precious gift, time. Time is the divine will expressed in the creation…every moment is a beginning.”
  — (01:12:19)

Timestamps for Important Segments

• 00:00–03:41 — Introduction, personal context, and the mood before Rosh Hashanah
• 06:02–14:11 — The darkness and pivot-points of Rosh Hashanah in Jewish tradition
• 21:24–27:45 — International recognition of Palestine: symbolism vs. practical outcomes
• 31:36–36:09 — The imperative to defeat Hamas before peacemaking, and Western public opinion
• 41:40–48:12 — Israel’s struggles with public diplomacy and global narrative
• 48:12–54:21 — Egypt and Syria: peace, war, and regional vectors
• 58:38–01:04:02 — Grassroots anti-Hamas movements in Gaza and future prospects
• 01:07:13–01:12:19 — Zionism as agency; Israel’s choices in the coming year
• 01:12:19–01:18:20 — The ongoing act of creation; philosophy of time; holiday blessings

Final Reflections

Haviv concludes with a philosophical blessing, rooting hope in the Jewish spiritual tradition: that new paths always exist, and even in the darkest hours, the possibility of wisdom, agency, and better choices remains. The shofar’s cry, he insists, should jolt us to awareness of new alternatives and our own capacity to choose.

“We are too clever, we were made too clever to believe that we are ever stuck. May we have the wisdom to choose better, smarter paths.” (01:18:12)

Summary prepared for those seeking an in-depth, nuanced understanding of Israel’s moment, through the lens of faith, tradition, history, and realpolitik, delivered in Haviv Rettig Gur’s reasoned and reflective tone.