THE LONG GAME WITH JAKE SULLIVAN & JOHN FINER
Episode: Iran After Khamenei & Pentagon vs. Anthropic (with Karim Sadjadpour)
Date: March 5, 2026
Guest: Karim Sadjadpour (Senior Fellow, Carnegie Endowment)

OVERVIEW

This episode tackles two enormous subjects:

1. The aftermath and implications of the death of Iran’s Supreme Leader, Ayatollah Khamenei, focusing on power transitions, regime survival, and the prospects for democracy or further authoritarianism within Iran.
2. The Pentagon’s contentious standoff with the AI company Anthropic, paralleled by OpenAI’s entry into U.S. defense contracting, raising urgent questions about public-private technology partnerships, AI in warfare, and the boundaries companies can set for their government customers.

Throughout, Jake Sullivan and Jon Finer leverage guest expertise from Karim Sadjadpour, one of the most respected Western analysts of Iran, to disentangle the fraught, dynamic situation in Tehran, connect it to U.S. and Israeli policymaking, and reflect on broader dilemmas facing American power in the age of both revolutionary change and revolutionary technology.

SECTION 1: THE IRANIAN POWER VACUUM POST-KHAMENEI

Karim Sadjadpour’s Personal Perspective

• Opening Reflection: Karim separates his hopes as an Iranian-American from empirical reality, citing data that the vast majority of authoritarian regime transitions yield a successor authoritarian regime—especially when violence sparks the change.
• Quote:
  “What I've learned over the years on Iran…is that around four out of five authoritarian transitions lead to another form of authoritarian government. And when that transition is triggered by either internal or external violence, the likelihood of a democratic outcome is much, much lower.” (03:18)

Khamenei’s Worldview—Resistance Over Compromise

• Khamenei typified the “hedgehog” (one big idea) approach (06:10). His regime was predicated on “resistance” to U.S. and Israeli pressure, preferring intransigence, even under threat, to any hint of concession.
• Khamenei wanted enmity with the U.S. for internal legitimacy—a strategy openly admitted by former President Khatami:
  “We need enmity with the United States, the revolution needs enmity with the United States.” (09:45)

Why No Compromise, Even at the Cost of His Life?

• Khamenei’s “survival instincts” clashed with his ideology of resistance. His failure of operational security—attending meetings despite open threats—may have reflected an acceptance or embrace of martyrdom in the twilight of his rule (09:07–09:45).

SECTION 2: IRAN’S FUTURE—STRONGMEN, NATIONALISM, AND THE PROSPECTS FOR DEMOCRACY

What Comes Next? Archetypes and Power Factions

• Short-term: The regime, battered but not broken, is in “existential fighting mode.”

• Medium-term scenarios (12:05): Iran’s post-Khamenei arc could resemble Soviet Russia, China, North Korea, Pakistan, or Turkey.

• Karim’s View:

  • The next strongman likely won’t be a cleric.
  • Nationalism, possibly “pluralistic Iranian nationalism” that accommodates multiple ethnicities, is poised to grow as the dominant political narrative—potentially for good or ill.

• Quote:
  “The winning argument in Iran in future years is going to be nationalism... you can have the negative nationalism of Vladimir Putin… or a positive patriotism…” (12:51)

Will Security Forces Take Over? Where Is the Democracy Movement?

• Revolutionary Guards are not monolithic; senior insiders are “revolutionaries” but many in the rank-and-file prefer pragmatism (17:22).
• Violence by security forces has splintered hopes for quick democratic change. Most Iranians long for a “normal life”—opportunity and dignity, not overt democracy per se (19:22).
• “It’s not to say that people don’t want democracy… what people say increasingly in Iran is we want a normal life [zendegiye normal]...” (19:40)

Public Sentiment Amid War and Repression

• As many as 80–85% of Iranians oppose the regime; the populace is “furious,” “shell-shocked,” and reeling from both government violence and collateral damage (21:27).
• Many wanted U.S. intervention, “a magic bullet only hurting oppressors,” but the realities of military escalation (e.g., bombing of a girls’ school with 200 casualties) shattered these hopes (22:30).
• “There hasn't been any winners here. The regime is obviously flailing. The Iranian society is in shell shock. Hasn't been good for America… lose, lose, lose all around.” (47:20)

SECTION 3: U.S. & ISRAELI STRATEGY—ARE THEIR INTERESTS ALIGNED?

Supporting Ethnic Militias: Dangers of “Playing with Fire”

• Speculation is rife that the U.S. or Israel may arm Kurdish or separatist factions within Iran to destabilize the regime. Sadjadpour strongly cautions against this (“opposite of sound,” 27:59):
  “If it's perceived that the U.S. Government or any outside power is... trying to factionalize the country, that is going to badly backfire…” (29:32)

Shared Goals, Diverging Tactics

• U.S. and Israeli ideal outcomes are similar (pre-1979-style Iran neutral or friendly to the West)—but Israel could accept protracted chaos and targeted assassinations, while the U.S. must weigh regional stability (34:17).
• Iran is seeking to “regionalize” the conflict, using attacks on Gulf States to pressure U.S. public opinion (35:25).
• “Israel may want to continue this campaign of targeted assassinations indefinitely… an Israeli prime minister is more willing to live with [the fallout] than an American president.” (35:07)

SECTION 4: SUCCESSION & THE FUTURE OF IRANIAN LEADERSHIP

The Rise (and Likely Short Reign) of Mojtaba Khamenei

• Mojtaba Khamenei, the Ayatollah’s son, is reclusive and even more hardline; likely interim, not transformational (39:56).
• As security becomes the regime’s sole pillar, hereditary succession undermines the very revolutionary identity that overthrew the Shah.
• “If Mujtaba succeeds him, he may not rule for 37 days.” (42:36)

Gulf States’ Calculus

• Iran’s regionalization of violence is beginning to unite Gulf neighbors with each other and the U.S., despite efforts to remain neutral (43:38). Pakistan’s nuclear defense pact with Saudi Arabia heightens the stakes (46:14).

What Should U.S. Policy Be?

• Sadjadpour advocates clarity and strategy, not improvisation:
  “It's absolutely critical for United States and the US President to be clear in his own mind, okay, this is what we're actually trying to achieve. This is the viable objective we have. And then how do we fulfill that objective?” (47:34)

SECTION 5: THE PENTAGON VS. ANTHROPIC—WAR, AI, AND GOVERNANCE

Contract Breakdown: Mass Surveillance & Lethal Autonomy

• Pentagon cancels Anthropic’s contract over disagreements on limits, notably on fully autonomous weapons and mass surveillance (55:20). OpenAI steps in and wins favor by (initially) accepting Pentagon’s terms.
• The Pentagon threatens to designate Anthropic a “supply chain risk,” an unprecedented and likely illegal move (60:57).
• “The threat by the Pentagon to impose a supply chain risk designation on Anthropic is outrageous. This is a patriotic American company. Ironically… they're the most forward leaning on these issues.” (59:14)

The Precedent and the Principle

• Anthropic’s principled objection is commended—yet the hosts worry about the risks if tech CEOs can impose their own policy priorities in warfare contracts (63:00).
• OpenAI, under pressure, later partially amends the contract with new guardrails against domestic surveillance (63:34).
• “In this particular case I'm very sympathetic to Anthropic… but the universalizing of this case makes me a little bit more nervous. I think the right answer… should be a responsible government... not a technology CEO.” (62:42)

Wider Implications

• The dispute weakens the U.S. in strategic technology sectors:
  “It is not comforting… to have a precedent where the government essentially tries to destroy a company… in a totally disingenuous way.” (66:36)
• Unlike previous defense industries, the government lacks a deep bench of expertise on LLMs, heightening the role and leverage of private innovators (68:37).
• U.S. government has already begun phasing out Anthropic—increasing strategic vulnerability and undermining trust (71:00).

MEMORABLE QUOTES & MOMENTS

• “There are few nations in the world with whom the United States has more common interests and less reason to quarrel than Iran.” – Henry Kissinger, quoted by Karim Sadjadpour (31:13)
• “If this is the country I'm not even saying a democratic government, but a government who prioritizes its own national interests, the US and Iran should be natural partners.” – Sadjadpour (32:04)
• “In some ways, I think probably for your very intelligent listeners, those archetypes are pretty self explanatory.” – Sadjadpour (13:07)
• “Almost certainly illegal as well… The Pentagon probably knows that, which is why they haven’t actually imposed it." – Sullivan, on the supply chain risk threat (61:10)
• “We've reached the bite off our nose to spite our face portion of the programming here.” – Sullivan, on U.S. agencies dropping Anthropic (71:37)

TIMESTAMPS FOR KEY SEGMENTS

• Khamenei’s Succession & Regime Futures: 00:58–25:02
• Democracy, Nationalism & the Public’s Mood: 16:19–25:02
• US/Israeli Policy Dilemmas & Ethnic Faction Armament: 27:11–35:25
• Who Succeeds Khamenei? Mojtaba & Regime Cohesion: 39:33–43:38
• Gulf States' Position & Regionalization of Conflict: 43:38–46:36
• What Should US Policy Be? 46:36–49:20
• Pentagon vs. Anthropic & AI, National Security: 55:20–72:00

CONCLUDING REFLECTIONS

The hosts and guest converge on a note of frustration, even sorrow:
Despite dramatic upheaval in Iran, every side appears to be a loser so far—regime, people, America, the region—due to both structural traps and muddled strategy. In parallel, the U.S.'s handling of breakthrough technologies risks shooting itself in the foot even as great power competition intensifies.

As Sadjadpour puts it:
“There hasn't been any winners here... lose, lose, lose all around.” (47:20)

FOR FURTHER READING

• Sadjadpour’s Foreign Affairs essay (referenced at 12:05; see show notes)
• Ongoing reporting on Pentagon–AI company conflict

This summary captures all essential insights, character, and memorable turns of phrase. For direct quotes and detailed analysis, consult the episodes’ timestamps.