WMD roll call: Khamenei, Saddam, Gaddafi, Assad, and Kim

Other factors weighed on his decision, not least economic and diplomatic. Libya had been labouring under international sanctions stemming from the Pan Am Flight 103 bombing, and had become a pariah in international relations.

For a while, the gamble seemed to pay off. Gaddafi was welcomed warily back into the diplomatic fold, his trademark tent appearing in the shadow of Europe's palaces and presidential estates, but the reprieve was fleeting. When the Arab Spring swept through Libya in 2011, NATO intervened militarily. Gaddafi's regime fell, and the man once known as 'the Colonel' met a brutal end at the hands of his own people.

Syria's experience

In 2007, Israeli warplanes destroyed a covert nuclear reactor that Bashar al-Assad had been building in Syria's north-eastern Deir ez-Zor region. A year later, Israeli commandos assassinated Brig. Gen. Mohammed Suleiman, al-Assad's top advisor and the official overseeing the clandestine nuclear programme.

When the Arab Spring reached Syria in 2011, al-Assad responded to peaceful protests with escalating violence, prompting US President Barack Obama to warn that using chemical weapons would constitute a "red line" and trigger "enormous consequences". That line was crossed in the summer of 2013, when al-Assad's forces reportedly deployed chemical agents against civilians, but Obama held back, opting instead for diplomacy.

Sensing an opportunity, Russian President Vladimir Putin brokered a US–Russian agreement under which al-Assad would dismantle his chemical weapons stockpile in exchange for international acceptance of his regime. Backed by Moscow, the deal paved the way for al-Assad's gradual reassertion of control in Syria.

He remained in power there until late last year when well-trained, well-armed rebels advanced at lightning speed through Syria's major cities, taking them over one by one. With Russia preoccupied in Ukraine, Syria's army melted away, and al-Assad fled to Moscow. The newly installed Syrian government, led by the rebels, subsequently dismantled all remaining elements of the country's chemical weapons programme.

North Korea's experience

In March 1994, the US issued an unequivocal warning: North Korea would not be allowed to get nuclear weapons. Two months later, Pyongyang withdrew from the Nuclear Non-Proliferation Treaty, signalling its nuclear ambitions.

Opting for diplomacy over confrontation, US President Bill Clinton struck an agreement with North Korea on 21 October 1994, under which the US, Japan, and South Korea would give Pyongyang two civilian nuclear reactors, ease sanctions, and supply heavy fuel oil, provided North Korea give inspectors access to its nuclear facilities.

The accord soon unravelled. In 2002, Washington accused Pyongyang of covertly continuing its weapons programme in violation of the agreement. Fuel shipments stopped and North Korea left the non-proliferation framework. By 2005, it said it had nuclear weapons, and on 9 October 2006, it conducted its first successful nuclear test.

Since then, North Korea and its leader Kim Jong-un have continued steering a defiant course. By January 2025, Pyongyang had conducted six nuclear tests. Donald Trump reportedly offered to end sanctions on North Korea if it voluntarily gave up its nuclear weapons, material, and facilities. The offer was politely rejected.

Iran's experience

After two years of negotiations, the Obama administration and its European allies reached a landmark agreement with Tehran in 2015. This would curtail Iran's nuclear programme and prevent its militarisation, in exchange for sanctions relief. Israeli Prime Minister Benjamin Netanyahu was aghast, as were several Arab states, who were closer to Iran's destabilising regional activities and its ballistic missile development.

In 2018, Trump withdrew the US from the deal and reinstated severe sanctions under a policy of "maximum pressure". Iran responded by escalating uranium enrichment levels from 3.7% to 60%, edging closer to the 90% threshold necessary for nuclear weapons. Returning to the White House in 2025, Trump found Iran in a much weaker position, having lost a key ally in al-Assad and seen its proxy militias weakened.

Trump issued a stark 60-day ultimatum: agree to a new nuclear deal or face military action. When the deadline passed, Israel struck Iranian targets on 13 June. And on 22 June, the US struck three Iranian nuclear facilities, with Trump later hinting at the possibility of regime change in Tehran—a far cry from the US president who vowed to not involve America in further Middle East wars.

Assessing options

Khamenei is now weighing his response against the backdrop of recent history, namely the experiences of Iraq, Libya, Syria, and North Korea. Each model offers distinct lessons and warnings regarding the pursuit or abandonment of WMD, whether nuclear or otherwise.

One scenario envisions ongoing military strikes between Tel Aviv and Tehran, accompanied by Iranian strikes on US interests across the region, becoming a war of attrition. Another scenario sees a deal being struck, trading the regime's survival for the dismantling of its nuclear ambitions.

Read more: Why Libya isn't the right model for Iran's nuclear climbdown

Another alternative would involve Iran withdrawing from international nuclear treaties and reviving its programme in the years ahead, under the expanded authority of the Islamic Revolutionary Guard Corps. Whatever he chooses to do, Khamenei's directives in the coming days will not just affect Iran and Israel, but the whole of the Middle East.