Preface: The End of an Era

At approximately 5 a.m. Tehran time on 28 February 2026 — 9 Esfand 1404 in the Persian calendar — Iranian state television confirmed what the world already suspected: Ayatollah Ali Hosseini Khamenei, 86, was dead. He had been killed in “the opening blow,” in the words of Israeli Defence Minister Israel Katz, of a massive coordinated US-Israeli assault on Iran codenamed Operation Epic Fury by the American side and Roar of the Lion by the Israeli. A precision strike, likely costing under $10 million by one expert estimate and guided by CIA intelligence of “high fidelity” regarding his exact position, had hit his compound in Tehran while he was in his office attending a meeting with senior officials. His daughter, son-in-law, daughter-in-law, and grandchild were killed alongside him. So were General Mohammad Pakpour, commander of the IRGC; General Aziz Nasirzadeh, the defence minister; and Ali Shamkhani, Khamenei’s senior strategic adviser.

Donald Trump announced the death on Truth Social, calling Khamenei “one of the most evil people in history.” Across Tehran and other Iranian cities, footage verified by the BBC showed crowds in the streets not mourning but celebrating — women lighting cigarettes from burning portraits of the Supreme Leader, chants of “Marg bar Khamenei” (“Death to Khamenei”) mixing with cries of “Javid Shah” (“Long live the Shah”). The government declared 40 days of national mourning; millions of its own citizens declared it a day of liberation.

He had ruled for 36 years and six months: the longest-serving head of state in the Middle East at the time of his death, and the longest-serving Iranian leader since the Shah he helped overthrow. What he built, destroyed, and left unresolved is the story of a generation.

I. The Nuclear Programme: Fatwa, Flexibility, and the Race to Breakout

No issue better encapsulates Khamenei’s method of governance — opaque, personally decisive, publicly deniable — than the nuclear programme he managed for three and a half decades.

The 2003 Fatwa: Religious Cover or Strategic Fiction?

In 2003, following a crisis over Iran’s clandestine enrichment facilities at Natanz and Arak, Khamenei issued a fatwa — a religious ruling — declaring nuclear weapons haram (forbidden under Islamic law). The ruling was first publicly cited at an IAEA meeting in 2005. It became Iran’s primary diplomatic shield for the following two decades: whenever Western interlocutors raised the question of weaponisation, Iranian diplomats would invoke the fatwa as proof that the Supreme Leader had closed the matter on religious grounds.

Western intelligence agencies were never fully convinced. Israeli intelligence assessed that the fatwa was never formally published — a legally significant omission in Islamic jurisprudence — and may not exist as a binding religious document at all. The Israeli outlet B’Hadrei Haredim reported bluntly in 2025: “The fatwa prohibiting nuclear weapons was never published — and probably does not exist at all” (בחדרי חרדים, 2025). A senior commander in the Iranian military urged Khamenei in early 2025 to revoke it, telling a British newspaper: “We have never been so vulnerable — this may be our last opportunity to acquire one before it is too late.” Even CIA Director William Burns, testifying to Congress, calibrated his language carefully: “We don’t see evidence that the Supreme Leader has reversed the decision he made in late 2003 to suspend the weapons program” — a formulation that implied a programme had existed and been suspended, not that one had never been pursued.

The JCPOA and “Heroic Flexibility”

By 2013, the sanctions architecture built by successive American administrations had sufficiently compressed Iran’s economy — the rial had collapsed, oil exports had fallen by half — that Khamenei permitted his negotiators to reach a deal. He framed his tactical concession to the world with characteristic grandiosity, calling it “morunati-e ghahramanane” — “heroic flexibility,” invoking a passage from Imam Ali about the necessity of strategic retreat. The 2015 Joint Comprehensive Plan of Action (JCPOA) capped enrichment at 3.67%, reduced the centrifuge count dramatically, converted the Fordow facility to a research centre, and imposed rigorous IAEA monitoring. In exchange, Iran received over $100 billion in sanctions relief, including access to frozen assets.

But Khamenei set explicit red lines before the talks even began, and his negotiators — loyal to him, not to President Rouhani — enforced them. He insisted on retaining the Fordow enrichment facility (a mountain-bored site near Qom, hardened against airstrike), and on limiting the talks strictly to the nuclear file, with Iran’s regional behaviour and human rights record explicitly off the table. The Washington Institute’s analysis of his pre-negotiation conditions noted: “Since then, Khamenei’s negotiators have remained loyal to those directives.” He approved the deal as a temporary tactical measure, never as a strategic shift.

Post-2018: Breakout Acceleration

When Donald Trump withdrew from the JCPOA in May 2018 and reimposed sweeping sanctions, Khamenei moved methodically to reassemble Iran’s nuclear leverage. By May 2019, Iran had announced it was suspending its JCPOA commitments. By 2021, enrichment had reached 20%. By mid-2022, Iran was enriching uranium to 60% purity — only one technical step from weapons-grade 90%. By early 2023, Western analysts estimated Iran’s breakout timeline — the time required to produce enough fissile material for one bomb — had collapsed to approximately 12 days, down from the 12 months the JCPOA had been designed to guarantee. As of the February 2025 IAEA report, Iran held nearly 900 kilograms of uranium enriched to 20% and 60% in gaseous form, with 118 cascades of centrifuges installed — 76 of them advanced models banned under the JCPOA. A Carnegie Endowment obituary for the JCPOA noted that Khamenei’s own speeches by 2025 “explicitly endorsed enrichment at 60 percent” while reaffirming his fatwa against weaponisation — a contradiction he never resolved publicly, and perhaps the central unanswered question of his legacy.

In June 2025, Khamenei publicly rejected an American proposal that would have required dismantling Iran’s enrichment infrastructure, declaring it “contrary to Iran’s national interests.” He did not live to see whether diplomacy or war would resolve the impasse.

II. The Axis of Resistance: Building a Regional Military Empire

If the nuclear programme was Khamenei’s existential insurance policy, the “Axis of Resistance” — the network of proxy forces stretching from Beirut to Baghdad to Sanaa — was his offensive strategic doctrine. He did not invent it; Khomeini had laid the groundwork. But under Khamenei, it became Iran’s primary instrument of regional power projection, absorbing billions of dollars annually and reshaping the geopolitics of the entire Middle East.

The Mykonos Precedent (1992)

The template for Khamenei’s approach to external threats was established early. On 17 September 1992, agents of the Islamic Republic assassinated three leading members of the Democratic Party of Iranian Kurdistan and their interpreter at the Mykonos restaurant in Berlin. On 10 April 1997, a German court — after a five-year trial — issued an international arrest warrant for Iranian intelligence minister Ali Fallahian and declared that the assassination had been ordered by a “Committee for Special Affairs” at the highest levels of the Iranian state. The court named its members: Khamenei, then-President Rafsanjani, Foreign Minister Ali Akbar Velayati, and intelligence minister Fallahian. Former President Abolhassan Banisadr testified as a witness that the killings had been “personally ordered” by Khamenei and Rafsanjani. The verdict triggered a diplomatic crisis; European Union ambassadors were recalled from Tehran. It was the first time a Western court had judicially found a foreign head of state to have ordered political assassinations on European soil.

The AMIA Bombing (1994)

Two years later came the deadliest single terrorist attack in Latin American history. On 18 July 1994, a car bomb levelled the AMIA Jewish community centre in Buenos Aires, killing 85 people and wounding more than 300. Argentine judicial investigators spent three decades assembling the case. The Abdorrahman Boroumand Center, citing NCRI testimony, reported that “the decision [to carry out the bombing] was taken in the National Security Council in a meeting on 14 August 1993. That meeting took only two hours, beginning at 4:30 and ending at 6:30 pm.” Once the decision was made, Khamenei personally issued a fatwa — executive order number 39 — ordering the operation to proceed, with implementation divided between the Intelligence Ministry and the IRGC Quds Force. The Times of Israel reported: “The final decision to attack the AMIA center was made by Khamenei and then-president Ali Akbar Hashemi Rafsanjani.” In April 2025 — just ten months before his death — Argentine special prosecutor Sebastián Basso formally requested the arrest of Khamenei, declaring that he “led the decision to carry out a bomb attack in Buenos Aires in July 1994 and issued executive order (fatwa) 39 to carry it out.” Argentine President Javier Milei praised the US-Israeli strikes that killed Khamenei, adding that “Argentina would continue to pursue others responsible for the attack.”

Hezbollah and the 2006 War

The IRGC had played a central role in founding Hezbollah in Lebanon’s Bekaa Valley in 1982, during Khamenei’s tenure as president. As Supreme Leader, he transformed this relationship into Iran’s most sophisticated strategic investment. By the time of the 34-day war of 2006 — triggered by Hezbollah’s capture of two Israeli soldiers — the organisation had evolved under Khamenei’s patronage into a state within a state, with an arsenal of over 14,000 rockets and a disciplined command structure trained by Quds Force officers. Khamenei backed Hezbollah’s war posture throughout, framing it as proof of the Axis of Resistance’s deterrent capacity. Israeli Hebrew media analysis from the Misgav Institute (מכון משגב) has noted that Hezbollah under Iranian tutelage became “a defensive belt around Iran, as preparation for a decisive confrontation with Israel” (מכון משגב לביטחון לאומי, 2024).

October 7, 2023: What Did Khamenei Know?

The October 7, 2023 Hamas assault on Israel — the deadliest single day for Jews since the Holocaust — generated intense scrutiny of Iran’s foreknowledge. The New York Times, reviewing the minutes of ten senior Hamas leadership meetings, reported in October 2024 that “Iran was aware of Hamas’s plan to launch October 7 attack.” The documents showed Hamas had carefully avoided provocations since 2021 to falsely signal it had been deterred — while simultaneously seeking Iranian material support for a major attack. However, the evidence is nuanced: Israel Hayom reported (ישראל היום, 2024) that Hamas Gaza chief Yahya Sinwar “decided to launch the terror attack without coordinating with the Iranian axis” — suggesting Khamenei knew the attack was coming in general but may not have co-authored the specific operational plan. A state-linked Iranian daily, Jomhouri Eslami, operating under Khamenei’s direct supervision, later published an assessment calling October 7 “a mistake that undermined anti-Israel movements in the region” — an extraordinary implicit rebuke from within the system. Hezbollah under Nasrallah opened only a “limited” northern front the following day, and Iran refrained from direct military action for months — suggesting Khamenei calculated, correctly, that full escalation would endanger the regime.

The Houthis and the Red Sea

Khamenei’s investment in the Houthis of Yemen — funnelling weapons, training, and advisers through the Quds Force — produced a remarkable strategic dividend after October 7. Beginning in November 2023, Houthi forces began attacking commercial shipping in the Red Sea, striking over 50 vessels in the first eight months alone and forcing a global rerouting of cargo traffic around Africa’s Cape of Good Hope. On 16 January 2024, Khamenei publicly praised the Houthi campaign, saying that “what Yemen is doing in support of the people of Gaza is truly worthy of praise” (Wilson Center, 2024). Reuters reported that IRGC and Hezbollah commanders were physically present in Yemen, directing Houthi attacks on Red Sea shipping. The Soufan Center noted a distinction that mattered for understanding Khamenei’s strategy: unlike Hezbollah or the Iraqi militias, the Houthis “swear fealty to their own leadership, and not to Iran’s Supreme Leader” — illustrating both the reach and the limits of Khamenei’s proxy architecture.

III. Domestic Repression: Blood at Home

The 1988 Executions: President in the Room

The largest single act of mass political killing in the Islamic Republic’s history took place in the summer of 1988, when Khamenei was still president. Ayatollah Khomeini issued a secret fatwa in July 1988 ordering the summary execution of political prisoners who refused to renounce their beliefs — primarily members of the MEK/Mojahedin-e Khalq but also leftists from other organisations. “Death commissions” — three-member panels of a religious judge, a prosecutor, and an intelligence ministry representative — were assembled across Iran. Prisoners were brought before them and asked a single question: Do you still support the MEK? Affirmative answers meant death; some sessions lasted mere minutes per prisoner.

The BBC Persian investigation, drawing on Montazeri’s private recorded meetings (released by his family in 2016), confirmed that Khamenei’s name as president appeared explicitly in discussions about the killings: the taped sessions named “Ali Khamenei, the president, Ali Akbar Hashemi Rafsanjani, the parliament speaker, Ahmad Khomeini, head of the Supreme Leader’s office, and Abdolkarim Mousavi Ardabili, head of the Supreme Judicial Council” as the senior officials whose positions were reviewed. The human rights organisation Justice4Iran states that “Seyyed Ali Khamenei, as president, bore responsibility for the massacre of thousands of political prisoners in 1988,” and that in Azar (December) 1988, Khamenei publicly defended the killings. A US Congressional resolution noted he was “reportedly aware of, and later publicly condoned the massacre.” Estimates of the death toll range from 4,000 (Amnesty International’s conservative figure) to 30,000 (MEK’s claim); serious scholarly estimates cluster around 4,000–5,000.

The 1988 massacre was the foundational crime that haunted the entire system. Ebrahim Raisi — who sat on a Tehran death commission as deputy prosecutor and was later made president in 2021, then died in a helicopter crash in May 2024 — carried this blood on his hands directly. That Khamenei elevated Raisi, and before that protected every other official implicated in the massacre, was not an accident. It was consolidation.

The 2009 Green Movement: Personal Intervention, Iron Fist

On 12 June 2009, Mahmoud Ahmadinejad was declared the winner of the presidential election with a suspiciously decisive margin over reformist Mir-Hossein Mousavi. Millions of Iranians — including the losing candidates and senior regime figures like Hashemi Rafsanjani — believed the result had been fabricated. Millions took to the streets in what became the Green Movement.

Khamenei’s intervention was personal, public, and irreversible. On 19 June 2009 — 29 Khordad 1388 — he delivered a Friday prayer sermon before the largest crowd assembled at Tehran University in years. In it, he declared that Ahmadinejad’s election had been a “divine assessment” (ارزیابی الهی), explicitly backed the declared result before the Guardian Council had even finished its formal review, and declared that his own views were “closer to those of the president [Ahmadinejad] than to those of my fifty-year friend” (a pointed reference to Rafsanjani). He warned that if protests continued, the blood would be on the demonstrators’ hands, not the security forces’. “By Allah’s favor, the presidential election was accurately held,” he told the congregation, and promised an “iron fist” if Western powers meddled.

The crackdown that followed was systematic: Basij militiamen beat protesters in the streets; Evin Prison and the notorious Kahrizak detention centre overflowed with detainees, several of whom died from torture — a scandal so severe Khamenei eventually ordered Kahrizak closed, though he absolved the system of responsibility. In February 2011, he placed Green Movement leaders Mousavi, Karroubi, and Rahnavard under house arrest — an extrajudicial confinement that lasted years. Reuters reported, drawing on three sources with direct knowledge, that at a crisis meeting on 17 November 2019, Khamenei ordered his security commanders: “Do whatever it takes to end it” — a template for every subsequent crackdown.

November 2019: The Bloodiest Crackdown

When Iran’s government announced a fuel price hike of up to 200% on 15 November 2019, protests erupted within hours across dozens of cities. The government’s response was immediate and lethal: a nationwide internet shutdown lasting approximately five days, which Amnesty International documented as designed specifically to conceal mass killings from external observers. Khamenei called protesters “vandals” in public statements. Reuters’s investigation, published in December 2019, reported that at least 1,500 people were killed in the initial days of the crackdown — a figure later cited in Wikipedia’s article on the protests. The UN and Amnesty International put the figure at over 300 confirmed deaths, with the real total likely far higher. Khamenei described the dead not as victims but as enemies of the state.

Mahsa Amini and Woman Life Freedom (2022)

In September 2022, Mahsa Jina Amini, a 22-year-old Kurdish-Iranian woman, died in the custody of the morality police after being arrested for allegedly improper hijab in Tehran. The “Woman Life Freedom” (Zan, Zendegi, Azadi) uprising that followed was qualitatively different from previous protests: it was explicitly anti-theocratic, explicitly anti-Khamenei, and led primarily by young women who burned their headscarves in the streets. Tens of thousands were arrested. Amnesty International documented unlawful lethal force used systematically. Khamenei blamed foreign enemies — the United States, Israel, and the UK — for “designing and directing” the protests, a formulation he would repeat in every subsequent crisis.

January 2026: The Final Crackdown

The protests that preceded Khamenei’s death were the largest and bloodiest in the Republic’s history. Beginning in Dey 1404 (December 2025/January 2026), nationwide demonstrations were accompanied by a near-total internet and phone shutdown from January 8. Iran International, drawing on senior government and security sources, reported that “at least 12,000 people have been killed” in what it called “the largest killing in the country’s contemporary history.” On 17 January 2026, Khamenei gave what would prove to be his penultimate major public speech, publicly acknowledging for the first time that “several thousand” people had died — blaming the United States and Israel for orchestrating the unrest and describing all the dead as “some martyrs, some deceived.” Intelligence reports emerging from early January 2026 indicated Khamenei had privately ordered a “Plan B”: arrangements for evacuation to Moscow if internal unrest led to the regime’s collapse. He never needed it; a US-Israeli airstrike reached him first.

IV. The Financial Empire: Setad and the Contradictions of Austerity

Perhaps the starkest moral contradiction of Khamenei’s reign was economic. He preached the doctrine of iqtisad-e moqavemat — the “Resistance Economy” — to Iranian citizens for decades: a programme of self-sufficiency, reduced dependence on oil revenues and Western trade, and willingness to endure sanctions rather than compromise on revolutionary principles. He urged Iranians to be “content” and “avoid waste” (his words, from a 2008 speech). Meanwhile, he sat atop a financial empire of extraordinary scale that answered to no parliamentary oversight, no judicial review, and no public accountability.

The Setad Empire

The organisation known as Setad Ejraiye Farmane Hazrate Emam — the “Headquarters for Executing the Order of the Imam” (EIKO), commonly called Setad — was established by a Khomeini decree in 1989. It was originally intended as a transitional body to manage abandoned properties and distribute charity. Under Khamenei, it became something entirely different.

A six-month Reuters investigation, published in November 2013, estimated Setad’s combined assets — real estate, corporate stakes, pension fund interests, and other holdings — at approximately $95 billion: a figure exceeding Iran’s annual petroleum export revenue at the time, and vastly larger than the estimated wealth of the last Shah. Reuters reporters identified nearly 300 properties Setad put up for auction in a single month. The organisation operated across telecommunications (it seized a major stake in Iran’s national telecom company), pharmaceuticals, construction, oil, and agriculture. Farsi sources — including VOA Persian and BBC Persian — reported on Setad’s methodology: courts were ordered by Khamenei’s representatives to hand over properties deemed “ownerless,” “abandoned,” or belonging to exiles, religious minorities (particularly Bahais and Jews), or opponents of the regime. Farsi Wikipedia notes that “under Khamenei, this organisation created a large financial empire under the personal control of the leader of the Islamic Republic” (ویکی‌پدیا فارسی، مدخل ستاد اجرایی فرمان امام).

Reuters was careful to note they found “no evidence that Khamenei uses Setad’s wealth for personal use” — but the distinction between personal and institutional control was, in the context of velayat-e faqih, essentially semantic. Setad funnelled billions into the IRGC, subsidised proxy forces across the region, and cushioned the regime from some effects of Western sanctions. It is designated under US Treasury Executive Order 13599. The organisation reports exclusively to the Office of the Supreme Leader — not to parliament, the president, or any other state institution.

Enriching the IRGC While Preaching Sacrifice

Beyond Setad, Khamenei transformed the IRGC into Iran’s dominant economic actor, engineering the privatisation of state industries in the 2000s in ways that systematically transferred assets to IRGC-connected entities. When Article 44 of the constitution — which mandated state ownership of core infrastructure — was revised in 2004, the primary beneficiaries of the resulting “privatisation” were IRGC holding companies, not private citizens. The IRGC today controls an estimated one-third or more of the Iranian economy, through direct holdings, subsidiaries, and front companies. Khamenei built this deliberately: an economically embedded military that had a material interest in the regime’s survival was more reliably loyal than any ideological bond.

V. Velayat-e Faqih Expanded: How Khamenei Outgrew the Role He Was Given

A Reluctant Pretender

The most startling fact about Khamenei’s selection as Supreme Leader is that, by the standards of Shia Islamic scholarship, he was barely qualified for it. When Khomeini died on the night of 3 June 1989, Iran’s constitution required the successor to be a marja-e taqlid — a Grand Ayatollah, a “source of emulation,” a figure who had earned the highest level of independent religious scholarship and a following of emulators who sent him their religious tithe. Khamenei held only the mid-rank title of Hojatoleslam. He himself knew it. A video clip from the 1989 Assembly of Experts session showed him admitting: “Based on the Constitution, I am not qualified for the job, and from a religious point of view, many of you will not accept my words as those of a leader.”

The solution was political engineering of a high order. Akbar Hashemi Rafsanjani — then Speaker of Parliament and Khamenei’s close ally — engineered a constitutional revision that removed the marja requirement, and the revised constitution was ratified by referendum on 28 July 1989. Khomeini had reportedly written a letter before his death to the Assembly’s chairman, clearing the way; the letter was published posthumously, its authenticity disputed by some. The Assembly voted 60 to 4 to confirm Khamenei. Within weeks, he was being retroactively promoted in official discourse: referred to first as “Ayatollah,” then — in defiance of normal clerical recognition processes — as “Grand Ayatollah.” Grand Ayatollah Montazeri, Khomeini’s chosen original heir and one of the Republic’s most senior jurists, publicly challenged the promotion: “The condition for marja is two things which the Supreme Leader does not have: the first is being most learned… the second is the ability to independently derive religious rulings.” This critique led directly to Montazeri’s house arrest — a confinement that lasted until 1997 and contributed to his estrangement from the regime he had helped found.

The “Government Decree” Mechanism

Once established, Khamenei systematically expanded the prerogative of the Supreme Leader’s office beyond anything envisioned in the original velayat-e faqih doctrine. The key mechanism was the hakm-e hokumati — “government decree” or “ruling of governance” — an instrument by which the Supreme Leader could override the decisions of all other state institutions. It was first deployed dramatically in August 2000, when the reformist-dominated Sixth Majlis moved to revise Iran’s restrictive press law. Khamenei sent a personal letter to Majlis Speaker Mahdi Karroubi ordering the Parliament to drop the bill, calling the proposed change “not lawful and not in the interest of the system.” The Parliament complied. In the BBC Persian account of Khamenei’s rule (بی‌بی‌سی فارسی, 2026), this moment is identified as a turning point: “The first time the term ‘government decree’ entered Iranian political discourse was in August 1379 [2000].”

He used the same mechanism in 2009 to override Ahmadinejad’s appointment of his son-in-law as a deputy president; in 2010 to reinstate the intelligence minister Ahmadinejad had tried to dismiss; and on multiple other occasions to correct or override decisions by elected presidents. As the Foreign Policy analysis noted in February 2026, the pattern was consistent: “From the optimism of the Second of Khordad movement after Khatami’s 1997 election, reformists were steadily weakened through press closures, mass disqualifications in elections, and systematic repression, with the crushed Green Movement of 2009 as the decisive rupture.”

Sidelining Five Presidents

Khamenei’s management of the seven presidents who served under him (from Rafsanjani’s first term in 1989 to Pezeshkian’s 2024 election) followed a consistent template:

VI. Syria, Iraq, and Yemen: Wars of Choice and Necessity

Syria: The $30-Billion Gamble

When the Syrian uprising began in 2011, Khamenei’s initial instinct was caution — Carnegie Endowment reported that he “expressed significant concerns about the substantial financial and operational commitments required for a large-scale ground intervention.” It was Qasem Soleimani, the IRGC Quds Force commander, and Hassan Nasrallah of Hezbollah who together persuaded him. Soleimani reportedly made the case directly: Syria was Iran’s “strategic depth,” its land bridge to Lebanon and Hezbollah’s weapons corridors. In early 2012, Khamenei committed, declaring publicly that “Iran will defend Syria because it supported the resistance line.”

What followed was the most ambitious Iranian military deployment in history. The Quds Force established 82 separate fighting units in Syria, amounting to approximately 70,000 armed men (an estimate provided by an IRGC general close to Khamenei, cited by the West Point Combating Terrorism Center). Iranian-funded Afghan and Pakistani Shia fighters — the Fatemiyoun and Zainabiyoun Brigades — were recruited and shipped to Syria. Hezbollah’s role became central to Assad’s military survival. Over 140 IRGC members were confirmed killed in Syria by 2015; the real toll was higher. Billions of dollars flowed annually from Tehran to Damascus.

In December 2024, everything collapsed. After a decade and an estimated $30 billion in Iranian expenditure, the Assad regime fell in eleven days to a rebel offensive. Syrian military units — hollowed by low pay and corruption — simply evaporated. The Israeli media (ישראל היום, 2025) had previously reported a key detail: the rebel advance succeeded in part because “Iranian forces and militias pulled out following Israeli airstrikes” — meaning Israel’s military campaign had preceded the political collapse. Khamenei’s largest strategic investment in the Arab world had returned nothing but a bill.

Iraq: The Empire of Influence

After the US invasion of 2003 removed Saddam Hussein, Khamenei moved methodically to fill the power vacuum. The Quds Force, under Soleimani, cultivated relationships with every major Shia political faction and armed group in Iraq. By the mid-2010s, Iran-backed militias constituted a significant fraction of the Popular Mobilisation Forces fighting ISIS — forces that were simultaneously killing Iranian proxies’ political enemies. Khamenei’s strategy was not occupation but permeation: ensuring that no Iraqi government could act against Iranian interests without facing internal disruption.

Yemen: The Lowest-Cost, Highest-Yield Investment

Yemen was Khamenei’s most cost-effective proxy investment. The Houthis received Iranian weapons, training, and crucially — after October 7, 2023 — operational direction for their Red Sea campaign. For a relatively modest Iranian investment, the Houthis succeeded in disrupting one of the world’s most vital maritime trade routes, forcing a rerouting that cost global trade an estimated $10–15 billion in delays and additional shipping costs. Khamenei called it a triumph of the Axis of Resistance.

VII. Surprising and Lesser-Known Facts

1. He confessed his own illegitimacy. At the 1989 Assembly of Experts session where he was selected as Supreme Leader, Khamenei publicly stated that he was constitutionally unqualified for the position and that most of the clerics present would not accept his religious authority. This admission was captured on video. He then spent 36 years consolidating the exact power he admitted he should not have had.

2. He was a literary translator. Before the revolution and in the early years of the Republic, Khamenei translated several major works into Persian, including selections from Che Guevara’s writings and other revolutionary literature. The man who would imprison and execute leftists had spent his youth translating left-wing icons. He was also a published poet under the pen name “Ammar.”

3. His right hand was paralysed for 44 years. The 1981 bombing at Tehran’s Abuzar Mosque — a bomb concealed inside a tape recorder placed in front of him — permanently disabled his right arm and damaged his vocal cords. He delivered every speech, signed every decree, and waged every war of his Supreme Leadership as a physically diminished man in chronic pain. His characteristic gesture of raising only his left arm during sermons was not a stylistic choice.

4. He was not supposed to stay. A video clip from the 1989 Assembly of Experts session shows that Khamenei was initially discussed as a caretaker candidate for approximately one year — time for the system to identify a more qualified candidate. He never relinquished the position.

5. He had a “Plan B” evacuation route to Moscow. Intelligence reports emerging in January 2026 — during the massive nationwide protests that preceded the US-Israeli strikes — indicated that Khamenei had ordered preparations for an emergency evacuation to Russia if the regime collapsed. It was a remarkable admission, buried in classified cables, that the man who had projected invincibility for 36 years had quietly prepared for defeat.

6. Argentine prosecutors formally sought his arrest just 10 months before his death. In April 2025, special prosecutor Sebastián Basso requested an arrest warrant for Khamenei specifically for his role in the AMIA bombing — making him, while still alive, the subject of an international arrest request for a 1994 terror attack he had personally authorised with a fatwa. He was never served.

7. He privately viewed October 7 as a strategic mistake. A state-linked Iranian newspaper operating under direct supervision of his office described Hamas’s October 7 attack in October 2025 as “a mistake that undermined anti-Israel movements in the region” — an extraordinary implicit critique suggesting Khamenei or at least his inner circle understood the attack had triggered the chain of events that led directly to the destruction of his proxy network, his nuclear programme, and ultimately his own life.

8. He once opposed the Iran-Iraq War. After Iraqi forces were expelled from Iranian territory in 1982, Khamenei — along with Prime Minister Mousavi — privately favoured ending the war rather than invading Iraq. Khomeini overruled him and pushed the war for six more bloody years. This episode is rarely noted: the man later celebrated for his “strategic patience” was overridden on the most consequential strategic decision of the Republic’s first decade.

VIII. The End: Operation Epic Fury and What Comes After

The chain of events that led to Khamenei’s death on 28 February 2026 traced directly to October 7, 2023. Hamas’s attack — which killed 1,200 Israelis — triggered the Gaza war; the Gaza war drew in Hezbollah; Israel’s destruction of Hezbollah’s leadership (Nasrallah killed September 2024), followed by the fall of Assad in Syria (December 2024), and a 12-day Israeli air campaign against Iran in June 2025 — which smashed nuclear and missile facilities and killed several close associates — left Khamenei isolated, his Axis in ruins, and the domestic situation catastrophically unstable.

The December 2025–January 2026 protests, which Khamenei suppressed with a brutality that, by his own acknowledgement, killed “several thousand” people, failed to stabilise the regime. The CIA provided Israel with what officials described as “high fidelity” intelligence on Khamenei’s movements — he had reportedly failed to take adequate precautions in the final days before the strike. The New York Times reported (March 1, 2026): “The operation also showed the failure of Iran’s leaders to take adequate precautions to avoid exposing themselves at a time where both Israel and the U.S. sent clear signals that they were preparing for war.”

At approximately 3:11 p.m. local time on 28 February 2026, Israeli aircraft struck his compound in Tehran. Thirty bombs were reported to have hit the site. Khamenei was confirmed dead several hours later by Iranian state television — 40 days of national mourning were announced by the government as Iranians took to the streets in celebration.

He had entered history as an unlikely, self-admittedly underqualified caretaker. He left it as the architect of a regional military-theological empire that consumed hundreds of thousands of lives, enriched the institutions of repression, and ultimately consumed itself. What replaces the velayat-e faqih he so radically expanded is, as of March 1, 2026, the central unanswered question of the Middle East.

Key Sources

English (Primary):

Hebrew:

Farsi:

This article was researched and written March 1, 2026, drawing on sources in English, Hebrew, and Farsi published between 1992 and March 1, 2026. All translations from Farsi and Hebrew are the researcher’s own, based on original text.