As Israeli bombs fell on the supreme leader’s compound in Tehran on Saturday morning, Ayatollah Ali Khamenei was meeting above ground with several of his top advisers. He never saw it coming.
A Culmination of Strategy
The joint U.S.-Israeli operation that killed Khamenei was the culmination of two months in which President Trump pursued both diplomacy and war – on parallel tracks. On Friday, he chose war. The crisis began with the public uprising in Iran in late December, and was characterized by twists, last-minute reversals, and deliberate disinformation. The ambiguity itself proved a strategic asset, leaving Iran’s leadership vulnerable to what officials described as the largest aerial attack ever conducted by the Israeli military.
How the Operation Unfolded
The seeds of Saturday’s operation were planted in late December, when Israeli Prime Minister Benjamin Netanyahu visited Trump at Mar-a-Lago. At the time, anti-regime protests had just begun in Iran, and their significance was not yet clear. Netanyahu used the meeting to discuss a follow-up to last year’s joint strikes – focused on Iran’s ballistic missile capabilities – tentatively planned for around May.
Within days, the situation changed. The regime cracked down on protests with force, resulting in thousands of deaths. Trump responded on Truth Social, writing “HELP IS ON ITS WAY,” and urging protesters to take over government institutions. On January 14, Trump was on the verge of ordering strikes but pulled back, instead ordering a massive military buildup in the Middle East and beginning secret planning for a joint operation with Israel. Over the following weeks, the Mossad director visited D.C. Twice, followed by the Israeli military intelligence chief and the IDF chief of staff, coordinating Operations Epic Fury and Roaring Lion.
Diplomacy as Leverage
At the same time, Trump explored whether military leverage could produce a deal with Iran on his terms. The U.S. And Iran met in Oman in early February for the first time since last June’s 12-day war. Days later, Netanyahu traveled urgently to Washington to discuss U.S. Red lines in the negotiations and whether a joint military operation would be launched if talks failed.
From the start, Trump’s envoys Jared Kushner and Steve Witkoff were skeptical about the chances of a deal, but three U.S. And Israeli officials stressed that the initial nuclear talks in Geneva were not a complete ruse. Trump wanted to attempt to reach an agreement, and the Iranians were told explicitly that military strikes “would occur if we did not see real progress on a real deal very quickly,” according to a U.S. Official.
A week before the Geneva meeting, the U.S. And Israel agreed on a potential window for launching the attack – the coming Saturday, when Khamenei held a routine meeting with his top aides at his government compound. Keeping Khamenei from suspecting an attack and retreating to his underground bunker presented a specific challenge.
The Final Hours
When Kushner and Witkoff traveled to Geneva on Thursday, they suspected there was no deal to be had but still went through with the meeting to maintain the appearance of diplomacy. “One of the rules of deal-making is that you have to know very quickly if there’s a deal to do or not,” a U.S. Official said. After the first session, Kushner and Witkoff called Vice President Vance and reported that the gaps remained wide. A second round that evening changed nothing.
“Kushner and Witkoff saw that the Iranian proposal was bullshit and only meant to buy time,” a senior U.S. Official said. “There wasn’t any ‘there’ there to work with.” Another official described Iran’s strategy as “games, tricks, stall-tactics.”
U.S. Officials said there were three areas where Iran refused to compromise: its nuclear program and enrichment activities, its ballistic missile program, and its financing of regional proxies. Intelligence similarly indicated that Iran was rebuilding nuclear facilities previously claimed by Trump to have been “obliterated” in Operation Midnight Hammer last June.
After Geneva, Oman’s foreign minister flew urgently to Washington and met with Vance on Friday in a last-ditch attempt to delay Trump’s decision. But the president had already made up his mind. When an Arab official asked Witkoff on Friday whether an attack was imminent, the White House envoy dodged the question.
On Saturday morning, Khamenei convened his aides as U.S. And Israeli planners had anticipated. Two other gatherings of Iranian security and intelligence officials were taking place above ground in Tehran at the same time. Minutes later, all three were struck simultaneously. “If the Iranians had come to Geneva and given Trump what he wanted, he would have pulled the brakes on the military track. But they were arrogant and thought he wouldn’t take action,” an Israeli intelligence official said. “They were wrong.”
Frequently Asked Questions
What prompted the U.S. And Israel to take military action against Iran?
The operation was the culmination of two months in which President Trump pursued both diplomacy and war, following a public uprising in Iran in late December. The U.S. And Israel determined that Iran was not willing to negotiate a deal on terms acceptable to them.
What were the key sticking points in negotiations between the U.S. And Iran?
The U.S. Could not reach an agreement with Iran on three key areas: its nuclear program and enrichment activities, its ballistic missile program, and its financing of militant groups across the region.
When did the U.S. And Israel decide to launch the attack?
The U.S. And Israel agreed on a potential window for launching the attack a week before the Geneva meeting, targeting a Saturday when Khamenei held a routine meeting with his top aides.
Given the gravity of this situation, what impact might this event have on regional stability and international relations?
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