Ayatolla murder: The red line six American presidents refused to cross

For decades, the Pentagon ran war games that always ended the same way: a strike on Iran's supreme leader triggers a regional inferno that makes the Iraq war look like a skirmish. Bill Clinton had opportunities. George W. Bush had reasons. Barack Obama had the intelligence. Joe Biden had the drones. None of them gave the order.

Then, in the early hours of February 28, 2026, a coordinated US-Israel strike killed Ayatollah Ali Khamenei, the man who had dominated Iranian politics for more than 35 years, along with roughly 40 senior commanders and officials. The strategic restraint that defined American policy since 1979 was abandoned in a single night.

The question now, barely a week into the conflict, is whether Donald Trump has stepped into a confrontation that successive US administrations spent nearly five decades trying to avoid – and whether the consequences long anticipated are finally here.

For decades, the office of Iran's supreme leader remained effectively off the US target list. The reasons were not merely political caution; they were grounded in strategic, legal and practical considerations developed over years of policy deliberation.

As Jonathan M. Winer, a former US diplomat who served as Special Envoy for Libya, noted in an analysis last year, US policy since the 1970s has included a formal prohibition on assassination, most clearly articulated in Executive Order 12333. The rule emerged after a period of controversial covert operations that had damaged US credibility and produced long-term diplomatic repercussions.

According to Winer, the prohibition was not symbolic but rooted in legal and strategic calculations. "A foreign head of state – particularly one with religious authority – would not be considered a lawful target," he wrote.

When Trump publicly threatened Khamenei in June 2025, declaring that the US knew his whereabouts but would not "take him out (kill!) – at least not for now," Winer warned that such language carried risks that could not be dismissed as merely symbolic. "Even if not operationally actionable, the message could be interpreted by others, including regional actors, as indicative of future US conduct."

Those warnings now look prophetic. The 2020 strike that killed Qassem Soleimani was different, Winer noted. Soleimani was a military commander operating in a conflict zone, and the strike was framed as defensive. Killing the supreme leader in peacetime, absent any imminent threat, crossed a threshold that fundamentally changed how Iran would respond.

Alireza Nader, a former researcher at Rand and the Foundation for the Defense of Democracies captured the uncertainty immediately after the strike: "Something tells me that this won't be the easy regime-overthrow war Trump and Bibi have promised. I hope I am wrong. But I wonder if US-Israel war planners are underestimating the regime's resilience and its ability to inflict major pain on all sides involved."

The geography of vulnerability

Analysts note that war planners may have underestimated the regional ripple effects: a conflict conducted within or near the economies of allied states inevitably forces those partners to reassess the costs and risks.

The strikes that killed Khamenei prompted immediate retaliation across the Middle East. Iranian missiles struck the US Navy's Fifth Fleet headquarters in Bahrain, Al Udeid Air Base in Qatar – the largest American installation in the region – Al Dhafra Air Base in the UAE, and Al Salem Air Base in Kuwait. Explosions were reported in Riyadh. Qatar, Kuwait and the UAE closed their airspaces.

The UAE described the attacks as a "flagrant violation of national sovereignty and international law" and added that it "reserves its full right to respond to this escalation." Translation: you got us hit.

Within days, the damage was staggering. According to unverified but widely circulating reports, Saudi Arabia, the UAE, Kuwait and Qatar are now discussing withdrawing from US contracts and canceling future investment commitments to alleviate economic strain. While the specific claim remains emerging intelligence, the structural conditions that would produce it are all documented.

Saudi Arabia held 254 billion riyals in US equity exposure as of Q4 2025. The Gulf Cooperation Council states collectively represent somewhere between $3 and $4 trillion in US-linked financial commitments spanning sovereign wealth funds, defense contracts, and bilateral investment treaties. The UAE alone has pledged $1.4 trillion in US investments over the next decade.

Now count what has happened to the countries holding those commitments in the eight days since the strikes began. Qatar's LNG complex at Ras Laffan was struck and production halted. Saudi Aramco's Ras Tanura refinery took a drone hit and shut 550,000 barrels per day. Kuwait's Ahmadi refinery was hit by debris. The UAE has absorbed over 1,072 drones and 196 ballistic missiles. Seventy percent of flights in the UAE, Qatar and Bahrain have been canceled. Hormuz traffic has collapsed by 80 percent.

The countries experiencing all of this are not the countries that started the war. They are the countries that host the bases from which the war is being conducted.

Israeli journalist Alon Mizrahi put it starkly: "In only four days, Iran has managed to expand its sphere of military dominance in the region. Iran has destroyed the most valuable and expensive military bases, property, and equipment in the entire world. The American bases in Bahrain, Kuwait, Qatar and Saudi Arabia are among the largest military facilities in the entire world. These facilities have cost trillions of dollars over several decades to build. We are talking about the fact that the bulk of the military spending that has been made over more than 30 years has gone up in smoke."

Mizrahi's conclusion was even more arresting: "No enemy in a conventional war has ever done this to American military forces as Iran is doing right now."

The energy weapon reversed

The 1973 oil embargo began with a calculation: Arab states decided the cost of the existing relationship exceeded the cost of weaponizing the dependency. The mechanism was energy then. The mechanism now is capital.

The Strait of Hormuz handles around a quarter of global seaborne oil trade and a fifth of LNG supply. A senior adviser to Iran's Revolutionary Guard told state television that Iranian forces "won't allow a single drop of oil to leave the region." While that is partly propaganda, the reality is that tanker traffic has already slowed to a crawl, insurers have suspended coverage, and freight rates for very large crude carriers jumped 94 percent from Friday to Monday.

Analysts at Wood Mackenzie estimate oil prices could rise to "well over" $100 a barrel if flows are not restored quickly. Brent hit $82 this week, up from $66 at the beginning of February.

The last time prices reached those levels was after Russia's invasion of Ukraine in 2022. That shock sent inflation soaring across Africa, including Kenya, where fuel prices directly translate into higher transport and food costs.

Kenya is particularly exposed. More than 400,000 Kenyans work in the Gulf under the "Kazi Majuu" programme, with Saudi Arabia hosting the largest share. Their remittances, which hit record levels in 2025, sustain families back home. If companies slow projects or flights remain disrupted, those contracts become precarious.

The East African warned this week that a Hormuz shutdown would drive up grain, fertiliser and fuel costs across Africa, while reducing remittances from Africans in the Gulf. Somalia, Ethiopia, Djibouti, Eritrea and Sudan all trade heavily with Gulf states. The Gulf Cooperation Council's $100 billion investment footprint across Africa now faces serious disruption.

President William Ruto's statement condemning the strikes on Gulf States without mentioning the US-Israel trigger now looks less like diplomatic clumsiness and more like a failure to grasp how deeply Kenya's interests are tied to de-escalation. Former Kenyan UN envoy Martin Kimani warned that the Horn of Africa remains exposed to external shocks, given its reliance on global supply chains as a net importer.

The Iranian response nobody expected

What has surprised world is not that Iran retaliated, but how effectively it has done so. US Central Command reported that more than 30 Iranian vessels have been sunk or destroyed in Operation Epic Fury, including frigates, a drone carrier the size of a World War II aircraft carrier, and multiple submarines. Admiral Brad Cooper casually announced, "We're now up over 30 ships" in a briefing, adding "and as we speak, that Iranian drone carrier is currently on fire."

But Iran's naval losses, while significant, have not stopped its missile campaign. The country has spent decades investing in asymmetric deterrence – underground missile complexes, dispersed command networks, hardened infrastructure, and mobile launch platforms. This model was specifically designed to neutralize the traditional advantage of technologically superior air forces.

Destroying surface installations does not eliminate the deeper military capability beneath them. The Islamic Revolutionary Guard Corps claimed that all Israeli and US military targets in the Middle East have been struck "by the powerful blows of Iranian missiles" and warned retaliation would continue until the enemy is defeated.

Mick Mulroy, a former Pentagon official who oversaw Middle Eastern defense policy in the first Trump administration, said the president was taking a big risk in calling for Iranians to rise up. "This is by definition an existential threat and the regime will brutally repress it," Mulroy said. "More brutal than before."

Initial indications suggest the "rally-around-the-flag" effect is real. Jonathan Teubner, chief executive of FilterLabs, which uses social media to study shifts in attitudes, said the attack was creating a "textbook rally-around-the-flag effect" with promises of retaliation amplified across Iranian messaging platforms.

The global fallout

The ripple effects are already being felt far beyond the Middle East. European gas futures nearly doubled after the conflict began, hitting their highest levels since 2023. The QatarEnergy facility, which accounts for around a fifth of global LNG supply, declared force majeure to affected buyers. Asian buyers heavily dependent on Qatari gas now face competition with Europe for limited supplies.

Fertilizer markets are also exposed. Around 44 percent of sulfur, 31 percent of urea, 18 percent of ammonia and 15 percent of phosphates – all key fertilizer components – transit the region. Any sustained disruption could compound inflationary pressures in food markets, particularly in emerging economies.

Danish shipping giant Maersk suspended vessel crossings in the Strait of Hormuz, rerouting all services around the Cape of Good Hope. That detour adds 14 days to transit times and increases freight costs dramatically. Mediterranean Shipping Company suspended all bookings for cargo to the Middle East until further notice.

"The idea that this was going to be a calmer year, that freight rates were going to settle down, that supply chains might begin to return to normal – all that is totally off the table now," Peter Tirschwell, vice president for maritime and trade at S&P Global Market Intelligence, said.

The allies Washington forgot to ask

The Trump administration insists the strikes were necessary. Energy Secretary Chris Wright told the UN Security Council on March 5: "For 47 years, this brutal dictatorship has spread chaos, death, and instability around the world. President Trump has been clear on Iran. Iran's brutal regime will not prevail."

But the question that haunts this conflict is whether "prevailing" means anything when your allies' economies are burning, your shipping lanes are closed, and your adversary's deepest military capabilities remain intact.

Former President Barack Obama, who negotiated the nuclear deal Trump abandoned, watched the escalation with visible dismay. "I am deeply concerned that we have abandoned the diplomacy and international consensus that we worked so hard to build a decade ago," he said. "The people of Iran deserve freedom and dignity, but true sovereignty arises from the will of a people, not from the rubble of a destroyed national infrastructure."

The Gulf States are now quietly recalculating. They are not threatening to leave the American security umbrella – not yet. But they are reminding Washington that the umbrella is a transaction, not a tribute. When the principal exposes the agent to unilateral risk without consent, the agent eventually quantifies the cost of the relationship relative to the cost of revising it.

It is not just the Gulf allies who are recalibrating. Across the Atlantic, European partners are no longer willing to be dragged into a war they had no part in starting.

Spanish Prime Minister Pedro Sánchez delivered a stinging rebuttal to Trump this week after the US president threatened to impose a full trade embargo on Madrid for refusing to allow the use of its jointly run military bases for strikes on Iran. In a televised address, Sánchez framed the conflict as a symptom of a broader breakdown in global order. Reflecting on the wars in Ukraine and Gaza, and reaching back to the 2003 invasion of Iraq, he summed up his government's stance in three words: "No to war."

Trump told reporters this week that Americans could face retaliatory attacks at home. "I guess," he said when asked about the risk. "When you go to war, some people will die."

That is the calculation every previous president made and rejected. The consequences they feared were not theoretical – they were American bases burning, global oil markets in turmoil, allies reconsidering their commitments, and a hardened Iran potentially racing for a bomb.

All of those consequences are now unfolding simultaneously. The key question is whether the Trump administration has a strategy for what comes next, or whether the assumption was that removing the supreme leader would neutralise the threat rather than trigger further complications.

For more than four decades, Iran structured its defence posture around preparing for this possibility. Over roughly the same period, successive US administrations largely sought to avoid a direct conflict with Tehran. How the current confrontation evolves may therefore test the durability of these long-standing strategic approaches.