There’s a tempting logic to the analogy. The Trump administration orchestrated the dramatic removal of Nicolas Maduro in January — a swift, tactically audacious operation that produced an oil deal, a compliant interim government and a triumphant press conference at Mar-a-Lago. Why not replicate the formula in Tehran?
Maximum pressure, a credible military threat, a transactional offer and a deal. It’s the art of the deal applied to rogue states, and it worked once.
The problem is that Venezuela and Iran inhabit entirely different strategic universes, and conflating them reveals a fundamental misunderstanding of what drives foreign policy behavior — not personality, not leverage, but interests.
The Venezuela operation succeeded, to the extent it did, because of a convergence of structural conditions that had nothing to do with Trump’s negotiating genius. Maduro had himself repeatedly offered a pathway out — floated proposals, made overtures on oil and migration — because he was operating from a position of genuine weakness.
The Venezuelan military didn’t resist in any meaningful way. Cuba, which had provided security forces loyal to Maduro, lost dozens of personnel in the operation, but no major power stepped in to defend him. Russia condemned the action rhetorically; China issued a statement about sovereignty. Neither moved a single battalion.
Maduro was, in the language of realpolitik, an isolated client whose patrons had decided he was not worth a war. The US was operating in its own hemisphere, against a regime that had no nuclear program, no ballistic missiles and no serious capacity to retaliate against American assets abroad.
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.
Trump’s special envoy Steve Witkoff aimed to finalize a deal within 60 days; Iranian Foreign Minister Abbas Araghchi noted that key differences remained, with deep mistrust between the two parties. Sixty days is barely enough time to translate a framework, let alone resolve 45 years of enmity.
As Henry Kissinger once observed about linkage — and it’s an observation that the architects of the Trump administration’s Middle East policy would do well to revisit — the effectiveness of any coercive strategy depends entirely on whether the target state’s interests can actually be satisfied by what you’re offering.
Venezuela’s interests, in the end, were compatible with the Trump deal. Iran’s are not. The ayatollahs are not Maduro, the Revolutionary Guards are not the Venezuelan military and the Persian Gulf is not the Caribbean. The June 2025 strikes severely damaged Iran’s major uranium enrichment facilities, but not its resolve to retain a nuclear program or its nuclear know-how.
The Venezuela template was always a regional exception, not a universal playbook. Applying it to Iran was less a strategy than a wish — and in foreign policy, as in markets, wishes have a poor track record against structural realities.
This article was originally published on Leon Hadar’s Global Zeitgeist and is republished with kind permission. Become a subscriber here.