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How Far Will Trump Go in Iran?

Ross Douthett hosts Mark Dubowitz, CEO of the Foundation for Defense of Democracies and longtime Iran hawk, to discuss the ongoing U.S.-Iran conflict. Dubowitz has worked on Iran policy for 22 years and advocates for regime change through maximum pressure and support for Iranian opposition movements.

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Key Takeaways
  1. 01

    Iran's ballistic missile production rate is now zero and their launchers have been reduced by two-thirds after three weeks of military operations

  2. 02

    Mark Dubowitz argues that total victory requires regime change in Iran, achieved through Iranian boots on the ground, not American ones

  3. 03

    The Battle of Hormuz represents a decisive moment that will determine whether Trump can claim major military success against Iran

  4. 04

    Iran's closure of the Strait of Hormuz was inevitable regardless of timing, but better fought when they are militarily degraded

  5. 05

    Trump wants a deal with Iran including no enrichment capability, returning HEU, and being 'low-key on missiles'

  6. 06

    Israel operates as Trump's 'pit bull on a leash' providing negotiating leverage against Iran for the next two and a half years

  7. 07

    The Iranian regime killed Iranian protesters on January 8th and 9th, deepening domestic opposition to approximately 70 million people

  8. 08

    Dubowitz estimates Iran would have pocketed a trillion dollars under the Obama nuclear deal with restrictions sunsetting this year

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Ross Douthett hosts Mark Dubowitz, CEO of the Foundation for Defense of Democracies and longtime Iran hawk, to discuss the ongoing U.S.-Iran conflict. Dubowitz has worked on Iran policy for 22 years and advocates for regime change through maximum pressure and support for Iranian opposition movements.

The conversation takes place roughly 24 hours after President Trump postponed strikes on Iran's power plants, amid conflicting reports about possible U.S.-Iran negotiations. Dubowitz argues the U.S. is winning its war against Iran based on Trump's stated objectives of destroying Iran's missile program, Navy, and nuclear capabilities.

The discussion covers three phases of potential victory: current military operations, continued degradation of Iran's repression apparatus, and maximum support for Iranian opposition. Central to the debate is whether the Battle of Hormuz can be won and what constitutes acceptable costs for American interests.

Military Degradation: Three Weeks of Unprecedented Success

Iran's ballistic missile production rate is now zero and their launchers have been reduced by two-thirds after just three weeks of U.S.-Israeli operations.

"Their ballistic missile production rate is now zero. Their launchers have been reduced by two-thirds" - Mark, describing the extent of military degradation achieved.

The Iranian Navy has been decimated and their nuclear program severely set back, building on damage from the 12-day war last year.

Israel has systematically eliminated Iran's repression apparatus since February 28th, including former Supreme Leader Ali Khamenei and top IRGC commanders.

The Three-Phase Strategy for Total Victory

Phase one involves major military operations lasting potentially six weeks total, severely degrading Iran's war-making capabilities across missile, naval, and nuclear domains.

Phase two continues Israeli strikes against Iran's repression apparatus - the IRGC, Basij, police forces, and intelligence services responsible for crushing opposition.

Phase three provides maximum support to Iranian opposition so "the next time they come to the streets, you have changed the equation and strengthened the opposition."

"All learning is anti-forgetting, so spaced repetition is key" - the strategy requires sustained pressure over time rather than one-time strikes.

The Battle of Hormuz: Inevitable Confrontation

Iran's closure of the Strait of Hormuz was inevitable, but better fought now when they are militarily degraded rather than with nuclear weapons and full capabilities.

"The Battle of Hormuz was a battle that was inevitable. The only question was, were we going to fight it in a way where we were stronger and they were weaker" - Mark.

Control of three key provinces critical to the Strait can be achieved through financial warfare, cyber operations, and economic strangulation beyond just military means.

Karg Island represents 95% of Iran's oil exports, 50% of the state budget, and $78 million annually - equivalent to three years of IRGC and intelligence apparatus funding.

Trump's Deal-Making Versus Regime Change Goals

Trump's stated terms include no enrichment capability, returning HEU, being "low-key on missiles," and sharing Hormuz with the Ayatollah.

"Trump always wants a deal" and has wanted one with Iran since his first term, making negotiations the likely outcome rather than full regime change.

Israel serves as Trump's "mad pit bull on a leash" providing negotiating leverage: "I can let it go... or you can negotiate with me and hear my terms."

The fundamental tension exists between Trump's limited military objectives and Israel's existential need for regime change at almost any cost.

Iranian Domestic Opposition and Regional Risks

Approximately 70 million Iranians (80% of the population) despise the regime and have repeatedly taken to the streets despite brutal repression.

The regime launched chemical weapons attacks against Iranian schoolgirls in 2023 to break the woman life freedom movement, demonstrating escalating domestic brutality.

Iran retains the will for apocalyptic strikes against Gulf infrastructure but may lack the capability after military degradation.

"If this regime stays in power, they win" - the ultimate measure of success requires preventing Iran from reconstituting capabilities over the next 6-8 years.

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Books Mentioned

That's Not What This Book Is About by Joanna Johnson

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