Donald Trump speaking at podium with Iranian oil tanker in Strait of Hormuz overlay

The Not So Art of the Deal in Iran

Trump vents that he can “destroy the trade” and “destroy the country” — but can’t charge a “little fee.” Meanwhile, Iran runs the very toll-booth leverage he has craved for 46 years. A textbook reversal of intention and consequence.

(Image courtesy of Hindustan Times - Strait of Hormuz)

In February 2026, President Trump stood at a White House podium and delivered a frustrated monologue: “I am allowed to cut off any and all trade… I can destroy the trade, I can destroy the country… but I can’t charge a little fee.” The Supreme Court had just ruled that the International Emergency Economic Powers Act (IEEPA) does not authorize unilateral tariffs. Trump could still impose full embargoes or sanctions — the nuclear options — but the flexible, transactional “little fee” he loves as a bargaining chip was off the table.

This moment captures a deeper irony playing out in U.S.–Iran policy. For nearly half a century, Trump has spoken openly about using raw leverage — including military force — to seize or control Iranian oil resources. Yet as the U.S. applies maximum pressure, Iran has adapted by turning the world’s most critical energy chokepoint into its own transactional weapon: a selective toll system in the Strait of Hormuz.

The 46-Year Obsession

A video montage compiled by MilkBarTV and shared by geopolitics professor Glenn Diesen traces Trump’s rhetoric from 1980 to 2026. During the Iran hostage crisis and Iran–Iraq War era, a younger Trump repeatedly suggested the U.S. should respond to Iranian provocations by “grab[bing] one of their big oil installations” and keeping it, or “do[ing] a number on Kharg Island.” The theme has remained consistent: Iran’s energy wealth represents leverage to be taken or denied.

“Donald Trump has talked about attacking Iran and stealing its oil for 46 years (1980-2026).”

This is not abstract foreign policy. It is the ultimate “Art of the Deal” tactic applied to geopolitics — maximum pressure to force submission or extract concessions.

The Judicial Clip

In Learning Resources, Inc. v. Trump (decided February 20, 2026), the Supreme Court ruled 6-3 that IEEPA does not grant the President authority to impose tariffs. The Framers reserved the taxing power (including tariffs) to Congress. Trump could still declare emergencies and cut off trade entirely — “destroy the trade” or even “destroy the country” via sanctions and embargoes — but the clean, adjustable fee or reciprocal tariff tool was stripped away.

His podium rant was the direct fallout: frustration that the system allows blunt-force destruction but not the nuanced transactional art he prefers.

Iran’s Counter-Deal

While Trump vents domestic legal constraints, Iran has operationalized the very leverage he has long discussed — but reversed.

In late March 2026, Iran’s parliament committee approved a formal management plan for the Strait of Hormuz, which carries roughly 20% of global oil and LNG trade. The system includes tiered transit fees (reports cite up to $2 million per tanker, sometimes framed per barrel in yuan or stablecoins), free or discounted passage for allies, and restrictions or harassment for U.S.-aligned vessels. Some European buyers, facing energy price spikes (oil up ~60%, natural gas doubled in spots, diesel nearing $200/barrel in places), are reportedly exploring selective deals — potentially settled outside the dollar.

“Iran just offered Europe a Hormuz deal… If America is so powerful, why is the EU considering a deal with the country America is bombing?” — @ElCruzSeb

This is asymmetric transactionalism in action. The U.S. maximum-pressure campaign (sanctions, military strikes, threats) was meant to weaken Iran and preserve dollar dominance in energy flows. Instead, Iran weaponizes geography: pay the toll, accept the currency terms, or face disruption. One major non-dollar energy/transit arrangement visibly accelerates de-dollarization trends that have been building for years.

Intention vs. Consequence

The reversal is stark:

The Supreme Court decision only sharpens the contrast. Trump can still pursue blunt destruction, but the flexible fee-based bargaining he favors is constrained — while Iran improvises its own version on the water.

What to Watch

Key Signals

  • Energy markets & currency flows: Any sustained shift toward euro/yuan/rial-denominated transit or oil payments would mark another visible crack in petrodollar norms.
  • European desperation vs. alliance cohesion: How far will the EU go to secure affordable energy while the U.S. maintains pressure on Iran?
  • U.S. workaround authorities: With IEEPA tariffs curtailed, expect heavier reliance on other statutes (Section 232, 301, etc.) or full embargoes — and fresh legal challenges.
  • Iran’s adaptability: Geography remains its strongest card. Selective enforcement of the Hormuz plan tests international maritime law and global willingness to pay for “safe passage.”

The Bigger Picture

This episode is less about one personality or one waterway and more about the limits of unilateral transactional power in a fragmenting world. Trump’s lifelong script meets judicial guardrails at home and geographic improvisation abroad. The result: the tool he wanted to monopolize is now backfiring while he tries to destroy the country instead.

The “Art of the Deal” was always about leverage. In Iran policy 2026, the leverage has changed hands — at least for now.

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