The Years-Long Lead-Up To U.S.-Israel Assassination Of Iran’s Khamenei

February 28, 2026, no doubt marks a pivotal date in Iranian and Middle Eastern history. The joint U.S.-Israeli assault, with the unsubtle codenames Operations Epic Fury and Lion’s Roar, devastated Iran’s leadership and missile program and was in many ways unprecedented in its scale and degree of coordination. By the end of the day, Iran’s long-ruling Supreme Leader Ayatollah Ali Khamenei was confirmed dead.

Where Iran and the region go from here is uncertain. What is already abundantly clear is that Khamenei’s assassination did not occur in a vacuum. It was the dramatic culmination of years of miscalculations in his standoff and proxy conflicts with these powers in the region, internal economic mismanagement, and political repression. An incremental series of events dating back to President Donald Trump’s first term through the October 7, 2023, Hamas attacks on Israel led to the supreme leader’s ultimate demise.

At the end of 2023, many observers anticipated that 2024 would be a year of succession in Iran. The octogenarian Khamenei prioritized the survival and continuity of the Islamist regime he inherited in 1989.

At home, the ayatollah’s regime had just emerged from the 2022 Woman, Life, Freedom protests demanding an end to the system’s myriad restrictions, such as mandatory hijab for all women. Regionally, Hamas sparked an unprecedented war with Israel after perpetrating the infamous October 7 massacres in Southern Israel. A deadly war ensued in the Gaza Strip.

For years, Iran and its most powerful regional proxy, Hezbollah in Lebanon, were plotting a similar cross-border operation for Israel’s northern Galilee, replete with massacres and hostage taking on a much larger scale. Hamas, in a sense, fatefully beat them to it. The Lebanese Shia group, led by veteran leader Hassan Nasrallah, had, with critical Iranian support and capital, amassed a much larger and more sophisticated arsenal of rockets and precision-guided missiles than Hamas, theoretically capable of devastating major Israeli cities. It didn’t unleash them in a large-scale attack. Instead, Hezbollah sought to bog down Israeli troops in low-level tit-for-tat exchanges of fire on the border, calculating it could avoid an uncontrollable escalation into a full-fledged war while diverting Israeli military resources from Gaza.

Hezbollah was the crown jewel of Iran’s regional self-styled Axis of Resistance network of proxy militias that spanned the region. Its hold and influence over these groups undoubtedly endured a major hit after President Donald Trump took the unprecedented action of assassinating Khamenei’s right-hand man, arguably the second most powerful person in Iran at the time, Qassem Soleimani, in a drone strike on his car in Baghdad on January 3, 2020.

With the force of personality and charisma that Khamenei admittedly lacked, Soleimani organized and oversaw these militias as head of the Islamic Revolutionary Guard Corps extraterritorial Quds Force. Mere months before Trump ordered his killing, Soleimani played a key role in the violent suppression of a peaceful protest movement of Iraqi youth railing against rampant corruption and overbearing Iranian influence in their country’s internal affairs, including the murder of unarmed demonstrators with sniper fire. It was described as “Iraq’s Tiananmen.”

Iran retaliated a few days later by hitting military bases in Iraq with ballistic missiles. While no U.S. troops died, several suffered traumatic brain injuries.

Tehran had set a precedent for how it would retaliate in the future.

On April 13, 2024, Khamenei ordered another telegraphed attack. After an Israeli strike destroyed the Iranian consulate’s annex building in Damascus, Iran felt compelled to retaliate with its first direct attack against Israel. It first launched drones, followed by barrages of ballistic missiles hours later, giving Israel, the U.S., and other allies enough advanced warning and time to prepare a defense that intercepted the vast majority of the incoming projectiles. President Joe Biden told Israeli Prime Minister Benjamin Netanyahu not to retaliate, urging him to instead “Take the win.” Israel settled for a pinprick strike a few days later.

Israel would act bolder the following July 31, when it assassinated senior Hamas member Ismail Haniyah in a precision strike while he was hosted in Iran’s capital, Tehran. Khamenei vowed Iran would retaliate again for the death of its guest. Little did he know then that his most important ally in the region would soon meet his end.

Nasrallah’s gamble of avoiding a major escalation with Israel cost him his life. Israel did escalate on the northern front in September 2024 with a devastating air campaign and the landmark covert operation that rigged thousands of pagers to simultaneously explode, injuring numerous Hezbollah members. None of the long-feared, large-scale Hezbollah missile barrages against Israel transpired. Then, in a move that retrospectively foreshadowed Khamenei’s death, Israel assassinated Nasrallah in his bunker on September 27 with powerful airstrikes that shook Beirut.

Iran retaliated directly again, this time using only ballistic missiles with little forewarning, on October 1. While more powerful than April, Israel withstood it. It returned fire on October 26, in a series of precision airstrikes targeting Iranian missile sites and air defenses, including several of Iran’s advanced, strategic Russian-built S-300 systems. Biden’s Middle East advisor, Amos Hochstein, quipped that Iran was “essentially naked” following the strikes on these systems.

Those strikes had direct implications for Khamenei’s safety. Satellite images had previously documented movements of an S-300 coinciding with supreme leader’s sojourns to Iran’s northeastern city of Mashhad.

Before their respective assassinations, Soleimani and Nasrallah coordinated Iran’s efforts to prop up the regime of Bashar Al-Assad during Syria’s bloody civil war that began in 2011. Hezbollah directly intervened in the conflict early in 2013. In one of the group’s cruelest and most grotesque exploits beginning in July 2015, its forces participated in the siege of around 40,000 people in the Syrian town of Madaya, subjecting civilian residents, including children, to agonizing starvation.

With his Iranian and Hezbollah backers reeling, and Russia focused on its war on Ukraine, Assad’s brutal rule was swiftly approaching its end. His opponents drove him into ignominious exile in Moscow and toppled his regime on December 8, 2024. Syria’s new rulers banned the IRGC from entering Syrian territory, hitherto a critical land corridor for supplying Hezbollah.

The year 2024 closed with the axis strategically weakened and Khamenei no closer to an orderly succession at home. To add insult to these injuries, Donald Trump would imminently return to the White House after winning a second term in the 2024 elections. Whether he realized it or not, Khamenei’s days were now numbered.

On June 13, 2025, Netanyahu announced the launch of Operation Rising Lion following a series of Israeli airstrikes in Iran that assassinated several military commanders with uncanny precision. The 12-day war ensued, with Israeli fighters dominating Iranian skies and targeting its missile and nuclear sites. Iran retaliated with more ballistic missile strikes focused on Israel. The possibility of Khamenei being assassinated in his bunker was openly discussed by Trump and in the U.S. media. Trump ordered Operation Midnight Hammer toward that war’s end, which saw strategic B-2 Spirit stealth bombers striking Iran’s main nuclear sites with powerful bunker buster bombs. Iran retaliated with another telegraphed ballistic missile strike against a regional airbase hosting U.S. troops, this time Al-Udeid in Qatar. The war ended shortly afterward.

Khamenei began 2026 with the most fateful move of his long life. With Iranians across the country protesting the dire living conditions and repression under his regime and the regime itself, the supreme leader’s loyal IRGC and Basij paramilitaries implemented an unprecedented internet and communications blackout. Under the cover of that blackout, Khamenei’s men massacred unarmed protesters with no apparent discrimination, using everything from heavy machine guns on crowds to machetes against individuals. More than 30,000 may have died, with more than 7,000 confirmed killings. Whatever figure, it was doubtlessly the deadliest protest massacre in modern Iranian history.

And there was no going back.

Trump condemned the massacres and pledged to help the Iranian people. The massacres peaked on January 8-9. Trump ordered a military buildup to the region that soon equaled the one that preceded the 2003 invasion of Saddam Hussein’s Iraq, while briefly engaging Iranian officials in “indirect” and ultimately pointless nuclear negotiations clearly aimed at buying time as forces amassed near Iran. Then Israel and the U.S. pounced early yesterday, prompting a wider Iranian retaliation targeting American bases and civilian infrastructure in several Arab Gulf countries and Iraqi Kurdistan in addition to Israel. Khamenei was, in Netanyahu’s words, “no longer” by the day’s end.

It’s clear he’d sealed his inevitable fate in January with the killing of so many defenseless Iranian civilians. In the wake of his death, there’s much uncertainty over whether this regime can survive and complete an orderly succession under war or whether Iran’s population heed Trump’s call and finish the regime Khamenei earnestly sought to preserve for another generation.

Long before his death, Khamenei was never realistically expected to adopt or modify his rigid beliefs and policies, or to ever admit grave errors in his conduct or judgment. In other words, he remained a bitter fundamentalist until the bitter end.

“What should not be expected of Khamenei is a volte-face while he lives,” Alex Vatanka presciently wrote near the end of his masterful 2021 book “The Battle of the Ayatollahs in Iran.”

“He is ready to take all his mistakes with him to the grave and will never apologize for his decisions.”