Boundless Insights - with Aviva Klompas

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 this milestone 150th episode of Boundless Insights, host Aviva Klompas speaks with Jonathan Conricus for a clear-eyed look at where the war with Iran stands as it enters its fourth week.
Despite official messaging pointing to steady progress - degraded missile and drone capabilities, targeted strikes on senior figures, and significant damage to Iran’s military infrastructure - the picture on the ground remains far more complex. Israelis continue to face daily attacks, the regime remains intact, and Iran is still able to disrupt global shipping through the Strait of Hormuz, with growing economic consequences felt far beyond the region.
The conversation examines the gap between battlefield gains and strategic outcomes, including whether the current campaign is producing meaningful long-term change or simply managing the threat. 
Conricus also weighs in on Iran’s use of energy infrastructure as leverage and the possibility of further escalation. The episode also explores one of the most critical unresolved issues: Iran’s stockpile of highly enriched uranium and what it would take to neutralize that threat. 
Finally, the discussion turns to the broader regional picture, including the state of the fight against Hezbollah in Lebanon and how that front fits into the wider conflict.
Guest Bio:
Jonathan Conricus is a senior fellow at the Foundation for Defense of Democracies focused on the Middle East. He served in the Israel Defense Forces (IDF) for 24 years as a combat commander in Lebanon and the Gaza Strip. He also served as a military diplomat, foreign relations expert, and international spokesperson. He recently retired as lieutenant colonel. Jonathan was the first Israeli officer to be seconded to the United Nations (UN), during which he provided military and strategic analysis for UN peacekeeping forces. He has directed social media and public diplomacy efforts and has extensive on- and off-camera experience from his years as a spokesperson.

Host Aviva Klompas speaks with Natan Sharansky about one of the defining challenges facing democratic societies today: why the West often struggles to recognize and confront evil.
Drawing on his experience as a Soviet dissident who spent nine years in prison, Sharansky reflects on how authoritarian regimes operate and why democratic societies frequently misunderstand them. The conversation explores why many in the West hesitate to clearly identify evil even when faced with terrorism, hostage-taking, and deliberate attacks on civilians. 
Sharansky discusses the dangers of moral equivalence, the erosion of moral clarity since the Cold War, and the recurring mistakes democratic societies make when confronting regimes that reject their values. He also reflects on the role fear can play within democracies themselves and whether, after a lifetime spent fighting for freedom, he remains optimistic about the future of free societies.
Guest Bio
Natan Sharansky is a Soviet-born Israeli human rights activist, former political prisoner, and leading voice on democracy and freedom. Born in Donetsk, Ukraine, Sharansky became a prominent spokesman for the Soviet Jewish and human rights movements and was imprisoned by the Soviet regime for nine years on fabricated charges of treason and espionage after seeking to immigrate to Israel. Following an international campaign for his release, he was freed in 1986 and immigrated to Israel the same day. Sharansky later served in several Israeli governments as a minister and deputy prime minister and went on to chair the Jewish Agency for Israel from 2009 to 2018. He is the recipient of both the U.S. Congressional Gold Medal and the Presidential Medal of Freedom, and in 2018 he was awarded the Israel Prize for his contributions to aliyah and the ingathering of exiles. Sharansky is also the author of several influential books on democracy, identity, and freedom, including The Case for Democracy and Never Alone.

As the war with Iran continues, the conflict is raising fundamental questions about how the United States uses military power and how President Trump’s foreign-policy doctrine may be evolving.
For years, Trump was closely associated with an “America First” approach that emphasized avoiding prolonged wars and limiting U.S. military involvement abroad. But the current campaign against Iran suggests a shift. 
In this episode, Aviva Klompas speaks with Elliott Abrams, a former deputy national security advisor and Special Representative for Iran. They examine how the war is unfolding so far, what might realistically be achieved militarily, and what the strategic endgame could look like.
The conversation also explores the domestic political tensions surrounding the conflict, particularly among Americans who supported Trump because of his opposition to “endless wars.” Abrams discusses whether the president is redefining what “America First” means in practice and whether the campaign against Iran signals a broader shift in U.S. foreign policy.
Finally, they step back to consider the global implications of the conflict and how Iran fits into the wider landscape of American adversaries alongside China and Russia.
Guest Bio:
Elliott Abrams is a senior fellow for Middle Eastern studies at the Council on Foreign Relations in Washington, D.C. He has held senior foreign-policy positions in several U.S. administrations, including serving as deputy assistant to the president and deputy national security advisor in the administration of George W. Bush, where he oversaw U.S. policy in the Middle East. During the administration of Donald Trump, Abrams served as Special Representative for Iran and Venezuela. Earlier in his career, he was an assistant secretary of state in the administration of Ronald Reagan. 
Abrams was educated at Harvard College, the London School of Economics, and Harvard Law School. He has served on numerous public commissions and advisory boards, including the U.S. Commission on International Religious Freedom and the U.S. Holocaust Memorial Council, and he is the author of several books on American foreign policy and the Middle East. 
More From This Guest:
Trump’s Rules of War in The Free Press

As the war in the Middle East unfolds, its consequences are being felt far beyond the battlefield. The conflict has triggered fierce debate about American involvement, Israel’s role in U.S. foreign policy, and the future of one of Washington’s most important alliances.
In this episode, host Aviva Klompas speaks with historian and former Israeli ambassador to the United States Dr. Michael Oren about how the current war fits into the broader chain of events that began with the October 7 attacks and the strategic miscalculations that helped bring the region to this point.
They examine new polling showing deep partisan divisions among Americans toward Israel. The conversation also explores the resurgence of conspiracy theories and antisemitic tropes circulating in political commentary and social media.
Guest Bio:
Michael Oren served in the IDF as a Lone Soldier in the paratroopers. He was Israel’s ambassador to the United States from 2009 to 2013 and later served as a Member of Knesset and Deputy Minister of Diplomacy.
He is the author of several New York Times bestsellers including Six Days of War, Ally: My Journey Across the American-Israel Divide, and Power, Faith, and Fantasy. Ambassador Oren published 2048: The Rejuvenated State in 2023 and is the founder of Israel Advocacy Group.
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The Free Press - From October 7 to Killing Khamenei by Dr. Michael Oren