Are We Heading Toward a Stalemate in Iran? – with Dennis Ross

Are We Heading Toward a Stalemate in Iran? – with Dennis Ross

Author: Boundless Israel, Inc. March 26, 2026 Duration: 26:19

Host Aviva Klompas is joined by Ambassador Dennis Ross to assess where the war with Iran stands several weeks in and whether the current trajectory is leading toward a meaningful outcome or a prolonged stalemate.

While Iran’s military capabilities have been significantly degraded and key infrastructure has been damaged, the broader strategic picture remains unsettled. The regime is still intact, continues to launch attacks across the region, and retains leverage over global energy markets through the Strait of Hormuz. This raises a central question: what has this campaign actually achieved, and what can it realistically achieve from here?

The conversation examines the gap between tactical success and strategic clarity, including what the United States is ultimately trying to accomplish and how “success” should be defined. Ross explores whether weakening Iran’s capabilities is enough to change its long-term behavior, or whether the current approach risks leaving the core threat intact.

They also discuss Iran’s ability to rebuild with support from China, Russia, and North Korea, its use of energy disruption as a form of deterrence, and the indicators that would signal meaningful pressure on the regime. Finally, the episode considers the risks ahead, from mission creep to broader regional escalation, and what policymakers should be watching as the war continues to unfold.

Guest Bio

Ambassador Dennis Ross is the counselor and William Davidson Distinguished Fellow at The Washington Institute for Near East Policy. He also teaches at Georgetown University’s Center for Jewish Civilization. For more than twelve years, Ambassador Ross played a leading role in shaping U.S. involvement in the Middle East peace process, dealing directly with the parties as the U.S. point man on the peace process in both the George H. W. Bush and Bill Clinton administrations. He served two and half years as special assistant to President Obama and National Security Council senior director for the Central Region, spending the first 6 months of the Administration as the special advisor on Iran to Secretary of State Hillary Rodham Clinton. His newest book is Statecraft 2.0: What America Needs to Lead in a Multipolar World (Oxford University Press, March 2025).


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 ICC Arrest Warrants Part 2 – with Michael Oren [not-audio_url] [/not-audio_url]

Duration: 20:54
In this episode of Boundless Insights, Aviva Klompas is with former Israeli Ambassador to the United States, Michael Oren, to discuss the consequences of the International Criminal Court’s (ICC) recent decision to issue…
The ICC Arrest Warrants Part 1 – with Eugene Kontorovich [not-audio_url] [/not-audio_url]

Duration: 16:47
In an unprecedented move, the International Criminal Court (ICC) has issued arrest warrants against Israeli Prime Minister Benjamin Netanyahu and former Defense Minister Yoav Gallant. This is the first time the ICC has t…
What is Zionism (and Why Does it Matter)? – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 27:19
What does Zionism really mean, and why does it matter? In this episode of Boundless Insights, we discuss the findings of a new study from Boundless that sheds light on one of the most misunderstood and debated concepts i…
Is Israel winning the war(s)? – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 34:48
In this episode of Boundless Insights, we assess the progress of the war. While Israel has seen strategic successes, such as dismantling top leaders of Hamas and Hezbollah and repelling Iranian attacks, serious issues re…
The Return of President Trump – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 19:48
In this episode of Boundless Insights, we’re talking about Donald Trump’s return to the White House and what it could mean for U.S.-Israel relations, the fight against antisemitism in America, and broader Middle Eastern…
The Amsterdam Pogrom – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 18:37
Host Aviva Klompas and Dr. Michael Oren are discussing the harrowing events that unfolded in Amsterdam on the evening of November 7, when hundreds of Israeli soccer fans were targeted in a brutal act of antisemitic viole…
Can Israel Bring its Hostages Home? – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 24:16
In this episode, we delve into one of the most heart-wrenching aspects of Israel’s ongoing conflict – the plight of the hostages. On October 7, 2023, Hamas and other terrorists carried out coordinated attacks, abducting…
The Iranian Endgame – with Dr. Michael Oren [not-audio_url] [/not-audio_url]

Duration: 26:12
In the inaugural episode of Boundless Insights, host Aviva Klompas sits down with Dr. Michael Oren to discuss the long-standing threat Iran poses to Israel and the broader Middle East.When we recorded this episode, Israe…