It took an audacious gamble from Israel and an increasingly brazen White House to bring an end to Ayatollah Ali Khamenei's 36-year reign.
As US and Israeli missiles rained down on Tehran for the second time in 12 months, Iran's supreme leader found himself out of options — a situation he had always worked hard to avoid.
Khamenei had to that point proven astonishingly adept at charting a course for Iran through the choppy waters of international relations, as well as maintaining an iron grip on power within his own country.
A conservative Islamic scholar with a head for politics, he succeeded his mentor, Grand Ayatollah Ruhollah Khomeini, under questionable circumstances in 1989, initially being appointed as a temporary leader due to his insufficient religious qualifications.
However, the quietly spoken cleric greatly increased the powers of his office and ruthlessly dispatched those that challenged his rule, going on to become the Middle East's longest-serving head of state.
Over three and a half decades, Khamenei established a network of Shia or Shia-aligned groups across the region, waged a proxy war against Sunni-majority Saudi Arabia, and proved a thorn in the side of both the United States and Israel.
His death leaves Iran's clerical regime edging towards collapse, and potentially marks a monumental shift in the power dynamics of the Middle East.
A committed revolutionary
Khamenei was born in 1939 in Mashhad, a city in north-eastern Iran widely considered the country's spiritual capital due to the presence of the Imam Reza shrine, a pilgrimage site for Shia Muslims.
The second of eight children to middle-class parents, he began learning the Koran in school at the age of four, going on to undertake seminary studies at a hawza (a Shia madrasa) before settling in Qom at 19 to further his religious studies.
It was in Qom that he first attended classes run by conservative cleric Ruhollah Khomeini, who would later gain a national following by fiercely opposing society-wide reforms carried out by the ruling Shah, Mohammad Reza Pahlavi.
Khamenei came also to oppose the Shah, becoming one of the leaders of the anti-monarchy protest movement sweeping the country in the 1960s and 70s, and using lectures and sermons to advocate for a form of government based on Islamic law.
By 1978, after six arrests and a brief period in exile, he had become a close confidant of his former teacher, the also-exiled Khomeini.
And when the country's anti-royal sentiment solidified into a unified effort to oust the Shah — led in part by Khomeini, though a number of secular factions were also involved — he became a prominent figure in what became known as the Iranian (or Islamic) Revolution.
After the Shah fled to Egypt and the remaining provisional government collapsed in 1979, Khomeini declared himself Iran's "supreme leader" and quickly moved to crush the country's resurgent pro-democracy movements, purging universities of liberal-minded academics and carrying out scores of political executions.
Khamenei held a number of government positions in the years that followed, including head of the newly created Revolutionary Guards — a branch of the armed forces with a mandate to protect the newly formed Islamic Republic, including from other branches of the military.
Iran-Iraq War, assassination attempt and presidency
In 1980, Iraqi dictator Saddam Hussein ordered the invasion of Iran, hoping to take advantage of his neighbouring country's relative disunity and cement Iraq as a regional superpower by seizing Iranian oilfields.
He also hoped to stop the spread of what was now known as Khomeinism — the idea that "Twelver" Shia Islamic jurists are the only legitimate religious or political authorities, a threat to Saddam's secular but Sunni-dominated Ba'athist regime.
By 1981, Ali Khamenei was serving as Khomeini's personal representative on the Supreme Defence Council, the body tasked with coordinating the war effort, and had made several trips to the front line.
In June of that year, while speaking at a mosque in Tehran after one such trip, a bomb hidden in a tape recorder placed in front of him exploded.
Khamenei survived, but his right arm was permanently paralysed, his lungs and vocal cords were damaged, and he spent six weeks in hospital.
It was the start of a concerted bombing campaign believed to have been carried out by the Mojahedin-e-Khalq, or MEK, a radical dissident group that never claimed responsibility for the attacks, but also never disavowed them.
Two months later, Iran's president was killed in a similar attack, and Khamenei was approached to run for the now-vacant office — created the previous year to serve as Iran's nominal head of government, while the supreme leader would remain the more powerful head of state.
He initially declined, believing his injuries were too severe for him to expend a great deal of energy on the position.
"That's why we are offering you the post," Khomeini's representatives reportedly told him.
Khamenei won the presidency in October that year with 95 per cent of the vote — an electoral feat rendered less impressive by the fact he had the fervent endorsement of all three of his rival, government-approved candidates.
The MEK bombing was later hailed as a transformative moment in Khamenei's career, with some believing his survival cast him as a "living martyr" among Iran's revolutionary elite.
As president, Khamenei oversaw a shift in momentum in the war with Iraq, driving Saddam's forces out of Iran and then back towards Baghdad in a counter-invasion intended to rouse Iraq's Shia majority (a decision he soon came to oppose, but Khomeini championed).
When Iraq took back the initiative in 1988, during Khamenei's second term — in part due to the use of chemical weapons on Iranian troops — he pushed the supreme leader to accept a ceasefire, which Khomeini reluctantly agreed to.
Between 1 million and 2 million people, mostly Iranians, are estimated to have died during the conflict, which ended in a stalemate with no changes to either country's borders.
Seizing and consolidating power
In 1989, upon the death of Ruhollah Khomeini, Khamenei was appointed Iran's supreme leader by the Assembly of Experts, an elected (though heavily vetted) group of senior clerics charged with selecting the country's lifelong leader.
Another, more senior cleric, Grand Ayatollah Hussein-Ali Montazeri, was originally the preferred successor, but had clashed with Khomeini over a wave of post-war political executions carried out the previous year.
While Khamenei was not a marja at the time, as was required by the constitution (a marja being a senior Twelver cleric, usually a grand ayatollah, with the power to make legal decisions) the assembly nevertheless chose to honour Khomeini's wishes and appoint Khamenei to the position, by a vote of 60 to 14.
The constitution would later be altered to remove the requirement that a supreme leader be a marja, an attempt to retroactively legitimise Khamenei's selection — though he was nevertheless controversially recognised as having attained marja status in 1994.
Despite initially being told his appointment would be temporary and largely ceremonial — a way of convincing him to accept the role, as it was later revealed he had privately acknowledged he was not religiously qualified — Khamenei took a much more active role in day-to-day governmental affairs than his predecessor.
Drawing on his time as president, he regularly intervened in political decision-making at all levels, relying on a web of carefully cultivated relationships in lieu of Khomeini's forceful personality and religious standing.
Where he arguably outshone his predecessor, though, was his ability to play his rivals off each other, striking a balance among competing interests that ensured no one faction of Iranian society — whether it be fundamentalists or reformists, clerics or civil servants, or different branches of the military — gained enough power to seriously challenge the status quo.
When little-known reformist Mohammad Khatami achieved a crushing victory in the 1997 presidential election, for example, Khamenei worked behind the scenes to stall serious reforms, employing tactics such as pressuring the judiciary to close liberal publications while maintaining a public image of being above the fray.
However, when an emboldened parliament began pushing for expanded press freedoms in response, Khamenei openly incited opposition to the move, writing a letter to legislators and ordering them to call off debate on the bill, resulting in scuffles on the floor of parliament.
With pro-Khamenei activists threatening to storm the building, the reformist Khatami found himself urging his more radical supporters to back down in the interests of avoiding widespread chaos — transforming Khatami himself into a moderating force against his supporters, a role he played for much of the rest of his presidency.
Similarly, when hardline president Mahmoud Ahmadinejad sought more control over the nation's security services in the wake of his widely disputed 2009 re-election, Khamenei went from being Ahmadinejad's most prominent backer to publicly humiliating him, booting his chosen vice-president from cabinet and reversing his sacking of a minister.
Safeguarding a brutal regime
This ability to read the ebb and flow of Iranian politics — to know when to yield to pressure and when to exert his office's full authority — was perhaps most on display in Khamenei's dealings with other politicians.
His response to the protest movements that swept Iran at seemingly regular intervals during his time in office, however, was rarely so nuanced.
A relatively well-educated country with a high population of unemployed youth, Iran is fertile ground for political uprisings — a fact Khamenei was keenly aware of, leading him to order several brutal crackdowns on student-led protests.
Whether they were demanding an end to the regime or simply calling for less strict hijab laws, demonstrators were often beaten, shot or spirited away by the country's Basij paramilitary, later to allege torture at its hands.
The most recent crackdown, in January of this year, resulted in the deaths of thousands of protesters.
During Khamenei's reign, Iran also regularly led the world in the number of executions being carried out per year, many of which were of political prisoners.
For a brief period in 2009, in the immediate wake of Ahmadinejad's widely disputed re-election, he appeared to acknowledge the concerns of protesters, announcing a review of the results and ordering his announcement be repeated on Iranian state radio every 15 minutes to quell unrest.
But once it became clear the controversy was catalysing a genuine mass protest movement, he declared the results showed "the miraculous hand of God" at work and moved to crush what had by then grown into the "Green Revolution".
Khamenei's style of foreign policy — quiet background diplomacy, while openly declaring the United States to be "the Great Satan" and funding a network of armed groups across the Middle East — revealed a tendency to bob and weave depending on the circumstance (and the audience).
"Iran needs enmity with America. The revolution needs enmity with America," he reportedly told Mohammad Khatami during his presidency.
Khamenei maintained that enmity up until the end, casting lopsided military clashes with Israel and the United States in June last year — which forced him into hiding and set back his country's nuclear program — as Iranian victories that "delivered a hard slap to America's face".
It took a second round of US strikes to ultimately end his reign.
He will be remembered as both a skilled politician and a brutal dictator, whose death could fundamentally reshape the politics of the Middle East.
