Trump's Venezuela Playbook The Wrong Script For Iran

Venezuela's most powerful remaining leverage was its oil - and that was precisely what the Trump administration wanted. The deal, such as it was, wrote itself. Iran is a different civilization entirely, and not merely in the metaphorical sense.

The demands the Trump administration reportedly made of Iran - giving up nuclear enrichment and accepting limits on its ballistic missile program - would leave Iran with few defenses against a future attack. This is not an unreasonable observation from Tehran's perspective.

A regime that watches what happened to Maduro, to Gaddafi, to Saddam Hussein and to the Taliban before American boots arrived, draws the rational conclusion that surrendering one's deterrent is an invitation to annihilation.

After green-lighting Israeli airstrikes and bombing Iran during negotiations in June 2025, Washington could offer no credible assurances that accepting its terms would protect Iran from future attack. The deal being offered was less a negotiation than a demand for capitulation, dressed in diplomatic language.

The notion that to make foreign policy work, all you need are astute and tough businessmen who approach adversaries the way they approach corporate counterparts is misleading, especially when the issues at stake involve war, peace and survival. In Venezuela, the transaction was relatively clean: oil for order, sovereignty exchanged for sanctions relief and an end to the military pressure.

But as I have observed, what is seen as progress in one arena can trigger chain reactions elsewhere - and Iran sits at the center of an entire regional architecture involving Russia, China, Hezbollah, the Houthis and a nuclear program that has been years in the making.

The Israeli and American strikes on Iranian nuclear facilities in June 2025 did not eliminate Iran's nuclear program; rather, they likely accelerated Tehran's determination to acquire a deterrent capability. This is the iron logic of coercive diplomacy when pushed past its limits: you cannot bomb a country into submission while simultaneously demanding it negotiate from weakness.

The Venezuela template worked because Maduro had nothing left to fight with and nowhere to run. Iran has asymmetric capabilities, regional partners, hardened ideology and - crucially - the memory of every prior American administration that promised engagement and then delivered either sanctions or strikes.

For diplomacy to be successful, both sides need to agree on the issues subject to negotiation and believe that peaceful resolution is more valuable than military engagement. That condition existed, however precariously, in Caracas.

It never fully existed in Tehran - not because Iranians are irrational, but because the gap between what Washington demanded and what any Iranian government could accept without internal collapse was simply too wide to bridge by transaction alone.