Negotiating with Terror: The Impossible Choices of a Hostage Deal – with Dr. Michael Oren

Negotiating with Terror: The Impossible Choices of a Hostage Deal – with Dr. Michael Oren

Author: Boundless Israel, Inc. February 3, 2025 Duration: 18:50

It has been almost 500 days since Hamas terrorists stormed into Israel, killing 1,200 people and abducting 250 hostages into Gaza. In recent weeks, a hostage deal has held, bringing some hostages home—but with it comes an emotional rollercoaster of relief, fear, and the devastating reality that some will never return.

This episode takes a hard look at where things stand. The release of hostages has been met with the simultaneous release of Palestinian prisoners, including convicted murderers, raising urgent questions about what this signals for the future. From Hamas’s perspective, hostage-taking has proven to be an effective strategy, forcing Israel to confront difficult decisions moving forward.

To help make sense of the good, the bad, and the painful, I’m joined by historian, diplomat, and former Israeli ambassador to the U.S., Dr. Michael Oren.

If you found this episode insightful, subscribe, leave a review, and share it with others. Learn more about Boundless: https://boundlessisrael.org/


In a world of endless takes and heated debates, finding clarity on issues facing Israel, antisemitism, and American Jewish life can feel overwhelming. Boundless Insights-with Aviva Klompas cuts through the noise with thoughtful, in-depth conversations designed to empower rather than just inform. This isn't about surface-level opinions; it's about engaging with the complex perspectives and difficult questions that define these critical topics. Each episode of the podcast brings you closer to understanding the nuances often lost in broader commentary, fostering a space for genuine dialogue. You'll hear discussions that are as substantive as they are accessible, moving from historical context to contemporary challenges. The goal is to provide listeners with a trusted resource-a place to find not just information, but the tools for deeper reflection. Tune in for a podcast that values thoughtful exploration over easy answers, all aimed at making sense of a complicated landscape.
Author: Language: English Episodes: 152

Boundless Insights - with Aviva Klompas
Podcast Episodes
The Middle East Entering 2026 – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 22:31
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X at @avivaklompas.In this episode, host Aviva Klompas is joined by former Israeli ambassador to the United States…
That’s a Rapaport on 2025 – with Michael Rapaport [not-audio_url] [/not-audio_url]

Duration: 32:51
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X at @avivaklompas.Aviva closes out 2025 with actor, comedian, and podcaster Michael Rapaport for a funny and thoug…
American Antizionism - with Shaul Kelner [not-audio_url] [/not-audio_url]

Duration: 40:44
Sociologist and Jewish studies scholar Dr. Shaul Kelner joins Dr. Rachel Fish to examine the rise of antizionism as a distinctly American political and social movement. Kelner argues that contemporary antizionism is less…
A Muslim Zionist’s Case for Peace – with Loay Alshareef [not-audio_url] [/not-audio_url]

Duration: 20:56
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X at @avivaklompas.Host Aviva Klompas speaks with Loay Alshareef, an Arab Muslim peace advocate whose personal jour…
Terror in Australia [not-audio_url] [/not-audio_url]

Duration: 25:56
Please donate to support and the families affected by the Bondi Beach terror attack: www.charidy.com/supportsydneyWe want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X…
Netanyahu Wants a Pardon – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 22:58
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X at @avivaklompas.Israel is facing a moment without precedent: a sitting prime minister on trial for corruption is…
A New Vision for Israel – with Dr. Einat Wilf [not-audio_url] [/not-audio_url]

Duration: 34:33
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org or message Aviva on X at @avivaklompas.In this episode of Boundless Insights, host Aviva Klompas speaks with Dr. Einat Wilf about her d…
The Price of Alliance – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 26:13
We want to hear from you. Send questions and comments to podcast@boundlessisrael.org, or message Aviva on X at @AvivaKlompas. Boundless relies on your support to produce courageous conversations and nuanced analysis at a…
Gaza and Israel After Phase One — with David Makovsky [not-audio_url] [/not-audio_url]

Duration: 45:15
Middle East analyst David Makovsky joins Dr. Rachel Fish to unpack the “phase one to phase two” handoff in Gaza: what the Trump plan actually changed, why returning the remaining hostages bodies still matters, and why an…