How Ayatollah Ali Khamenei was a sitting duck

By the time the Ayatollah began his day in Tehran, the spies listening to his calls were already extremely familiar with the habits of a supreme leader whose number was up. In orbit overhead, an Orion, the largest and most secretive of all American space satellites, could detect the voices of the regime as they exchanged increasingly worried messages about the build up of forces in the region. There were other high-tech efforts to track what is known as “life-pattern surveillance” of Ali Khamenei and his henchmen, including the now well-documented hacking of Tehran’s traffic camera network to track the movement of his bodyguards. All that remained in days and weeks before Khamenei’s killing, however, was the most prized asset of all: boots on the ground to confirm that all the technological surveillance was correct, that on a Saturday morning in Tehran, Khamenei would be a sitting duck. There, American intelligence officials turned to the masters of espionage in Iran: Mossad, Israel’s spy agency. Unrivalled in its experience of assassinating top military commanders and nuclear scientists, the agency was ultimately leading the plot to kill the supreme leader. It was only a matter of time before Khamenei and senior regime officials were eliminated, General Jack Keane, former vice-chief of staff of the US army and a trusted confidant of the Trump administration, told The Times. Indeed, there was little they could do to stop it, he said. “Although the Iranian leadership knew there was this risk, and changed their security procedures, even these changes had new habits which became predictable. Explaining the events that led up to Khamenei’s killing, Keane detailed an extensive intelligence operation that came to a stunning conclusion. “We were monitoring not just Ayatollah Ali Khamenei but the other leaders too,” he said. “And this is how we knew there was going to be a key meeting and that it would be in the presidential compound. We knew that Khamenei would not be in his bunker, given the meeting was scheduled for daytime, which provided a narrow opportunity to act.” Keane would know. The retired four-star general has long been one of the most influential military figures in Washington. When Donald Trump first won the White House in 2016, he wanted Keane to be his defence secretary but the general’s wife had just died, and Keane reluctantly declined the job. “We have a long experience in tracking high-value Islamic targets and the intelligence was very good,” he explained. “But Mossad provided the human intelligence, while we provided the other intelligence elements.” He said that the Israelis had “effectively taken up residence” in Tehran. “They resemble Persians as they speak Farsi without a hint of an accent and are well versed in the culture, customs and appropriate dress,” he said. “And they have developed scores of informants.” All this, said Keane, meant there was “no point” in the CIA attempting to have its own boots on the ground to “duplicate this sort of capability when they can rely on our close ally, which is the decision taken by previous administrations, given the multiple other threats worldwide that the CIA must entertain”. He added: “As such, we rely on Israeli human intelligence inside Iran and we don’t feel it’s necessary to replicate Mossad. We admire their dedication and continuous success they have achieved for many years. If the CIA’s human spying assets in Iran are limited, as Keane suggests, it enjoys technological superiority, deploying its Orion satellites and other overhead surveillance, such as the RC-135 Rivet Joint aircraft that can scoop up communications, and Reaper intelligence-gathering drones. Both these systems have been operating near and over Iran. During the planning stage of the mission, the CIA and the National Security Agency provided back-up in tracking the supreme leader’s habits and routines. Analysis of signals intelligence data collected by an Orion, operated by the US National Reconnaissance Office and capable of listening in on mobile phone conversations from more than 22,000 miles above the Earth, supported Mossad’s daily reports of the whereabouts of Khamenei. Sources suggest that, had the Ayatollah remained in his bunker, he would still have been targeted. There was a plan to take him out there but it would have been more complex. Instead of going down this route, there was judged to be a unique and brief opportunity with the Iranian leaders all coming together. Mossad had been tracking Khamenei for months and there was a question about whether they should go ahead themselves or wait for the Americans in a joint operation. Both Mossad and the CIA knew that Khamenei had alternative sites that could enable him to survive outside Tehran. And there was a fear, too, that he might be spirited out of the capital. But Mossad’s sources discovered that the Ayatollah would be meeting his top officials in central Tehran on Saturday. Both in Israel and the US, the meeting was considered too opportunist a gift to ignore. So the decision was taken to “seize the moment”. There have been claims however, that by staying in central Tehran and not fleeing, Khamenei may have wanted to die as a martyr. US military sources suggest that, if the ultimate objective of war is to break your enemy, the targeting of leadership can have a huge impact on the way a future operation goes. That appears to be Israel’s modus operandi. On September 27, 2024, the Israeli air force carried out an airstrike on Hezbollah’s headquarters in Beirut after receiving intelligence that the leader, Hassan Nasrallah, and his main commanders would all be together at a meeting. The death of Nasrallah and many of his commanders transformed the conflict between Israel and Hezbollah. The Israelis also learnt lessons from the 12-day war against Iran in June, when they assassinated key nuclear scientists and military commanders. In Operation Epic Fury, after the killing of Khamenei and some of his top commanders, Iranian ballistic missile launches were reduced by 50 per cent on day two, by 75 per cent on day three and by 86 per cent on day four. This was achieved not just by targeting Iran’s missiles, missile transportation systems and command and control with airstrikes but also with massive cyberattacks, US sources said. One US source said: “We knew from electronic eavesdropping that the Iranians planned to retaliate massively. Their thinking was that if on day one they could cause a lot of casualties it would begin to break the US and Israeli resolve. “They deliberately aimed most of their launches at the Gulf states. They hoped the Gulf nations would put pressure on the US to stand down because of the impact on oil prices and world economies and stability in the region.” However, the US has been knocking out Iran’s missiles, so the Iranians were prevented from carrying out the massive retaliation they had planned. The US military estimated that if Iran managed to launch salvos at the rate of 25 to 50 ballistic missiles at a time, a percentage would get through, even with the array of defences deployed. The Israelis have the Arrow anti-missile system, and the US have Thaad (terminal high-altitude area defence), Patriots and Standard SM-3 interceptors on Aegis guided missile destroyers. It turned out that Iran had only managed salvos of between two and five missiles, US sources said. Iranian drone strikes are also down by 73 per cent since the opening days of the war, according to General Dan Caine, chairman of the US Joint Chiefs of Staff. “We will now begin to expand inland, striking progressively deeper into Iranian territory,” he said at a press conference this week. Keane said the mission to eliminate Khamenei showed the effectiveness of human intelligence on the ground being supplemented by electronic surveillance. “Put it all together,” he said, “and you can find anyone and track them at any given time.” PLEASE BUY AGENT REDRUTH, MY NEW SPY THRILLER IN PAPERBACK. AMAZON, ROWANVALE BOOKS, WATERSTONES