WASHINGTON: The 36-year rule of Ayatollah Ali Khamenei built Iran into a powerful anti-United States force, spreading its military sway across the Middle East while using an iron fist to crush repeated unrest at home.
He was killed on Saturday, aged 86, Iranian state media announced, in air strikes by Israel and the US that pulverised his central Tehran compound after decades of efforts to resolve the dispute over Iran's nuclear programme diplomatically failed.
At first dismissed as weak and indecisive, Khamenei seemed an unlikely choice for supreme leader after the death of the charismatic Ayatollah Ruhollah Khomeini, who founded the Islamic Republic of Iran. But Khamenei's rise to the pinnacle of the country's power structure afforded him a tight grip over the nation's affairs.
Khamenei was "an accident of history" who went from "a weak president to an initially weak supreme leader to one of the five most powerful Iranians of the last 100 years", Karim Sadjadpour at the Carnegie Endowment for International Peace told Reuters.
The ayatollah criticised Washington throughout his rule, continuing to deploy barbs after the start of Donald Trump's second term as US president in 2025.
As a new wave of protests spread through Iran, with slogans such as "Death to the dictator", and as Trump threatened to intervene, Khamenei vowed in January that the country would not "yield to the enemy".
The comment was typical of the ferociously anti-Western Khamenei, in office since 1989.
By maintaining the hardline stance of Khomeini, the Republic's first supreme leader, Khamenei quashed the ambitions of a succession of independent-minded elected presidents who sought more open policies at home and abroad.
In the process, he ensured Iran's isolation, critics say.
Khamenei long denied that Iran's nuclear programme was aimed at producing an atomic weapon, as the West contended.
In 2015, he cautiously supported a nuclear deal between world powers and the government of pragmatist President Hassan Rouhani that curbed the country's nuclear programme in return for sanctions relief. The hard-won accord resulted in a partial lifting of Iran's economic and political isolation.
But Khamenei's hostility toward the US was undimmed, intensifying in 2018 when Trump's first administration withdrew from the nuclear agreement and reimposed sanctions to choke Iran's oil and shipping industries.
Following the US withdrawal, Khamenei sided with hardline supporters who criticised Rouhani's policy of appeasement towards the West.
As Trump pressed Iran to agree to a new nuclear deal in 2025, Khamenei condemned "the rude and arrogant leaders of America". "Who are you to decide whether Iran should have enrichment?" he asked.
Khamenei often denounced "the Great Satan" in speeches, reassuring hardliners for whom anti-US sentiment was at the heart of the 1979 revolution, which forced the last shah of Iran into exile.
Iran saw major student-led protests in 1999 and 2002. But Khamenei's authority was put to the test more profoundly in 2009 when the contested results of a presidential election that he had validated ignited violent street unrest, stoking a crisis of legitimacy that lingered until his death.
In 2022, Khamenei cracked down on protesters enraged by the death of Iranian-Kurdish woman Mahsa Amini, 22, who died in the custody of morality police in September of that year.
Faced with some of the most intense turmoil since the revolution, Khamenei blamed Western enemies and then resorted to the hanging of protesters and the display of their bodies suspended from cranes after months of unrest.