Breaking History: Eli Lake and Andrew Sullivan Debate the Iran War

Podcast: Breaking History by The Free Press
Date: March 19, 2026
Host: Eli Lake
Guest: Andrew Sullivan

Episode Overview

This special episode of Breaking History features an in-depth, wide-ranging conversation and debate between journalist Eli Lake and writer Andrew Sullivan centered on the ongoing Iran war. As the two sparring friends dig into the roots and current dynamics of U.S., Israeli, and Iranian policy, they explore the recent decision by the U.S. and Israel to undertake military actions against Iran, the wider strategic implications, historical context, and the moral and political dilemmas facing America and its allies.

Rather than focusing on the latest breaking headlines, Lake and Sullivan examine the historical trajectories, policy shifts, ideological changes, and recurring debates that underpin the crisis. The conversation is candid, spirited, sometimes personal, and occasionally contentious—offering deep insight for anyone seeking to understand how history shapes the present Middle East conflict.

Key Discussion Points

1. Context: Personal & Political Backgrounds

• Early Upbringing and Political Transformation
  • Eli describes growing up with secular, progressive, and Labor Zionist influences in Philadelphia and involvement in left-wing Jewish communities and summer camps, recounting his “God-optional” Judaism and early anti-nuclear activism.

    "So I, I gave a talk on Jewish perspectives on nuclear proliferation... At 13. And I was, it was very left." (10:32, Eli Lake)

  • Sullivan traces his early days in political journalism, noting the distinct difference between his trajectory and Eli’s, with Sullivan reflecting on the shifting tides in left and right political circles over the decades.

2. The American and Israeli Strategic Divergence

• The Oslo Accords and the Erosion of the Peace Process

  • Lake and Sullivan recall optimism of the 1990s surrounding Oslo and the subsequent collapse due to factors on both the Israeli and Palestinian sides.

    “The majority of liberal Jews were psyched about the Oslo and it was a huge breakthrough and it was the last time I think any of us felt any serious hope for the place.” (20:26, Andrew Sullivan)

  • The “Clean Break” memo and neoconservative strategies are dissected, with Lake pushing back on conspiracy theories about American foreign policy being dictated by Israeli priorities:

    “It's Americans who have a view of the Middle East that are defense intellectuals... it was a reflection of the undeniable connection between authoritarian regimes and the support of terrorism as a tool of statecraft.” (24:43, Eli Lake)

• U.S. Aid and Influence over Israel

  • Sullivan questions the logic of American largesse for Israel compared to other allies, arguing that special treatment persists far beyond rationale, and noting a double standard compared with NATO:

    “Why is there such a difference between [Trump's] relationship to a NATO ally... But when it comes to Israel, it's like, how much money do you need?” (42:41, Andrew Sullivan)

  • Lake argues Israeli military innovation and strategic partnership “pays back” American investments, citing the Iron Beam laser system:

    “Israel has developed a technology known as the Iron Beam, which shoots out missiles with a laser which is far more cost efficient. That is an Israeli technology that will… keep America's military at the leading edge...” (44:12, Eli Lake)

3. Settlements, U.S. Leverage, and Moral Stalemate

• Settlements and Influence
  • Sullivan condemns Israeli settlement expansion, arguing the U.S. has utterly failed at curbing it:

    “We have no influence… on none of the major issues in which we have disagreements have we…” (55:41, Andrew Sullivan)

  • Lake counters that past efforts (like Gaza disengagement) demonstrate Israeli capacity for withdrawal given the right conditions, and notes internal Israeli politics are not monolithic:

    “Sharon proved... Israel was capable of completely withdrawing… If there was a peace offer, I think it would be very painful. It certainly couldn't happen under this current political arrangement.” (59:07, Eli Lake)

  • Both acknowledge the deeply troubling rhetoric from current far-right figures in Israel’s government.

4. The Iran War: Rationale, Process & American Interest

• Diverging Rationales for the War

  • Sullivan criticizes the inconsistency and lack of clear justification for the U.S. and Israeli strikes, demanding to know the real purpose:

    “Why do you think [Trump] says something different every day? That’s my question.” (71:47, Andrew Sullivan)

  • Lake argues that Iran’s continued regional belligerence and missile buildup set the stage for action. He acknowledges the administration’s rhetorical confusion, noting Trump’s impulsive personality and lack of process.

    “The Iranians...were rapidly building up their missile capabilities and stockpiles so that they would have what... Rubio was [called] a conventional weapons shield in order to protect their nuke...” (73:49, Eli Lake)

• Did the U.S. Go to War for Israel?

  • Sullivan contends Israeli influence and pressure—especially from Netanyahu—were decisive:

    “It was Israel in the front leading the charge to accomplish something that Netanyahu said he's been trying to accomplish for 40 years.” (92:12, Andrew Sullivan)

  • Lake resists this narrative, pointing to Saudi pressure and longstanding American grievances with Iran:

    “It’s not just Israel that has an interest in ending the Islamic Republic...I just want to push back on this idea that it was just Israel.” (91:00, Eli Lake)

5. International Law, Morality, and Precedent

• Legality and Morality of the War
  • Sullivan is insistent that the war is illegal and morally dubious, especially the decapitation strike, warning of precedents and the breakdown of norms:

    “If the principle now is we cannot object and will not object to any power going into any other country and assassinating their entire leadership, we have no standing...” (84:29, Andrew Sullivan)

  • Lake argues that the nature of the Iranian regime renders “normal” standards of sovereignty obsolete:

    “You are making a category error because you are pretending that the leadership of the Islamic Republic is somehow like any other nation state...it is not the same as simply going and taking out the top leadership of Belgium.” (85:02, Eli Lake)

6. The Ghosts of Iraq and Libya: Process and Outcome

• Historical Lessons & Cautionary Tales
  • Both recall the disastrous fallout from Iraq and Libya, and the dangers of American overreach without congressional oversight or a solid exit strategy:

    “I am desperate not to see another human catastrophe unfold in the Middle East because we intervened militarily without thinking things through…” (120:36, Andrew Sullivan)

  • Lake draws a distinction with the current conflict, credits Israeli intelligence penetration, and anticipates the removal of the Iranian regime could enable a peaceful regional order:

    “The source of regional instability was a revolutionary regime in Tehran...If you remove that, that is a golden ticket for America to finally get out of the Middle East and then focus on the Pacific.” (115:36, Eli Lake)

7. Public Opinion and Domestic Politics

• Sullivan points out that American support for both the wars and the U.S.-Israel relationship is waning and expresses hope that political blowback might reverse the course in future elections:

  “A lot of people who voted for Trump really voted not to have a war like this… they’ve really fucked. And so… this could lead to a real wave in the elections...” (126:24, Andrew Sullivan)

Notable Quotes & Memorable Moments

• On Israel’s Nuclear Ambiguity

  “Israel went nuclear somewhere between Sergeant Pepper and the White Album.” (37:01, Eli Lake)

• On Double Standards of Aid

  "Why is there such a difference between [Trump's] relationship to a NATO ally... And when it comes to Israel, it's like, how much money do you need?" (42:41, Andrew Sullivan)

• On Personal and Policy Dissonance

  “It is the last 20 years that I've just had enough... So I'm in this relationship. I'm done. Right. And I think a lot of us here are done.” (62:26, Andrew Sullivan)

• On Decapitation Strikes

  “This is one of the greatest war crimes... In terms of international law, it’s a geopolitical mitzvah.” (84:16, Eli Lake; 84:19, Eli Lake)

• On History’s Unruliness

  “And all I'm saying is that then you also have the sheer serendipity of luck, timing... That's how history works. So it's a mess. It's a mix of these things.” (104:58, Andrew Sullivan)

Important Timestamps

• Backgrounds, Zionism, and Early Political Identity: 10:00 – 17:00
• Oslo, Right/Left Turns, and the 'Clean Break' Memo: 17:00 – 27:00
• US-Israeli Strategic Friction, Aid, & Settlements: 31:00 – 61:00
• Opening Rounds on Iran: Sabotage, Legality, and Pre-War Rationale: 70:00 – 85:00
• Rolling Out the War and Congressional Bypass: 90:00 – 108:00
• Debating Moral & Strategic Outcomes and Historical Parallels: 111:19 – 120:11
• The Future: Hegemony, Uprisings, and Hope/Fear for Iran: 120:13 – end

Tone and Dynamic

The conversation is intellectually combative yet marked by mutual respect, candor, and occasional humor. Both speakers’ exasperation—Sullivan’s moral outrage and Lake’s historical realpolitik—lends urgency to the debate. While never shying from confrontation, the discussion’s tone remains thoughtful, personal, and at times self-reflective.

Conclusion

This episode traverses not only the circumstances of the Iran war, but the moral, historical, and strategic entanglements defining America’s relationship with Israel, the nature of authoritarian regimes, and the recurring hazards of military interventions. For listeners looking to understand how history and ideology shape the present Middle East crisis, this dialogue is essential, offering clarity, disagreement, and hard-won perspective on a pivotal moment in U.S. and global politics.