Israel-Iran Shadow War on Verge of Exploding into the Open

An Iranian technician works at a uranium conversion facility.
In this Saturday, Feb. 3, 2007 file photo, an Iranian technician works at the Uranium Conversion Facility just outside the city of Isfahan 255 miles (410 kilometers) south of the capital Tehran, Iran. (AP Photo/Vahid Salemi, File)

On the evening of May 31 in the central Iranian city of Yazd, an Iranian aerospace engineer was returning home from dinner with a colleague when he suddenly felt ill and collapsed into unconsciousness. Ayub Entezari was rushed to hospital, where he died after several unsuccessful attempts to resuscitate him, according to an Iranian opposition media outlet. 

The cause of Entezari's death: intentional poisoning, said Saudi-financed  Iran International News, which operates a news site and broadcasts satellite television newscasts from its headquarters in London. 

The website posted a picture of a letter that local authorities sent to Entezari's family, calling the 35-year-old engineer a "martyr." Iranian officials use the term only for those who die defending the Islamic Republic. The website said Entezari, who held a doctorate in aerospace engineering from Tehran's Sharif University of Technology,  worked on Iran's  drone and missile development at a research facility in Yazd. 

Quoting unnamed sources, the website said Iranian security officials tried to locate the colleague, but the man had fled the country, the website said.  

Such unconfirmed reports sound like something out of Tehran, the Israeli spy drama now streaming its second season on Apple TV. Yet it's plausible that Israel's Mossad  was behind Entezari's  death. In recent weeks, the spy agency has resumed its campaign of targeted killings of Iranians -- just one front in a shadowy war that Israel and Iran have been fighting on land, sea, air, in cyberspace and through proxies since 1982.  And that war is heating up on several other fronts as President Joe Biden prepares to visit the Middle East later this month. 

With talks in Vienna to revive the 2015 nuclear deal now stalled and Iran continuing to enrich uranium to near-weapons-grade levels, the Israeli military is openly preparing dramatic new options for Prime Minister Naftali Bennett, should the talks collapse. Tehran has repeatedly threatened to destroy Israel, and Bennett, like his predecessors, has vowed never to allow Iran to develop a nuclear weapon. Last week, the Israeli military completed extensive air, sea and land exercises in the Mediterranean and in Cyprus, a portion of which simulated the distances its warplanes would have to fly to bomb Iran's nuclear facilities and make it back home. According to Israeli officials, airborne tankers refueled the warplanes twice. 

Meanwhile, Israel reportedly carried out yet another targeted killing on May 22, when two assassins on motorcycles pulled up alongside a car driven by Revolutionary Guards Col. Sayad Khodayee in Tehran and pumped five bullets into his head, leaving his body slumped behind the wheel of his Iranian-made Kia Pride, according to Iranian state media reports and photos. The assassins escaped, the state media said. 

A week later, a Revolutionary Guards leader Col. Ali Esmaelzadeh, died after falling from the balcony of his Tehran home. Iran International News, citing anonymous sources in Iran, reported that Revolutionary Guard officials suspected him of spying for Israel and threw him from the balcony. 

Both Esmaelzadeh and  Khodayee were a senior officers in the Guards' Quds Force, which trains, arms and pays a number of Shiite militias and political parties in the Middle East, including  Hezbollah in Lebanon, several groups in Iraq, and the Houthis in Yemen, as a way to extend Tehran's influence across the region.  In January 2020, the United States assassinated Quds Force commander Maj. Gen. Qassim Suleimani via a drone strike in Baghdad. 

Israel informed the Americans that it was behind Khodayee's killing, the New York Times reported, quoting an anonymous intelligence official who had been briefed on Israel's communication with the Americans. The intelligence official said the Israelis told the Americans that Col. Khodayee was the deputy commander of the Quds Force's covert Unit 804, where he had planned assassination plots against Israelis and other foreigners in Cyprus, Columbia, Kenya and Turkey. In April, the Mossad thwarted a Unit 804 plot to kill an Israeli consular official in Istanbul, a U.S. general in Germany, and a journalist in France. 

Under the unwritten rules in this shadow war, Khodayee's rank as a senior officer in the covert assassination unit made him a legitimate target, as were four Iranian nuclear scientists the Mossad  has assassinated in Iran over the past 12 years, including Mohsen Fakhrizadeh, Iran's top nuclear engineer.  According to Ronen Bergman, an Israeli intelligence reporter and author, Mossad takes its operational doctrine from the Babylonian Talmud, a 6th century compendium of legal arguments touching on all aspects of life. "He who comes to kill you, rise early and kill him first," it instructs. 

Iran May Fill Russia Vacuum in Syria

Another front in the shadow war could be heating up soon. With the war in Ukraine chewing through Russia's military manpower and its equipment stores, Moscow has redeployed its paramilitaries in Libya to the Ukraine campaign and may soon do the same with its forces in Syria. If that occurs, Iran will fill the vacuum with its own troops, predicted  King Abdullah II of Jordan, whose country borders on southern Syria. 

"The presence of the Russians in the south in Syria was a source of calm," the Jordanian monarch told former U.S. national security adviser H.R. McMaster on his Battlegrounds podcast last month. He cited the deconfliction agreements that Russian commanders reached both with the United States, whose special forces and Kurdish proxies have been fighting  remnants of the Islamic State; and with Israel, which has regularly conducted airstrikes against Iranian Quds forces and their proxies to prevent them from using Syria as a base for missile attacks against Israel.

"That vacuum [left by the Russians] will be filled by the Iranians and their proxies," King Abdullah said. "So unfortunately, we are looking at maybe an escalation of problems on our borders." 

Israel is also closely watching for signs of a Russian military redeployment from Syria and any inflow of Iranian forces,  their proxies and weapons. Of particular concern to Israeli intelligence is Iran's ongoing efforts to smuggle precision-guided missiles to their proxies in Syria, Lebanon and the Gaza Strip. According to Israeli Brig. Gen. Jacob Nagel and Jonathan Schanzer, a former U.S. Treasury intelligence official and now senior vice president of the Foundation for Defense of Democracies, a hawkish think tank, Israel's recent military exercises also included a simulated multi-front war against Iran-backed proxies in those countries and territories.

"The Israelis believe this is coming," Schanzer told SpyTalk, referring to an Iranian bid to replace the Russians in Syria. And while an increased Iranian presence in Syria would pose a danger to Israel, he said it also would present an opportunity, providing Israeli warplanes and drones with a  wealth of targets.

"If the Russians draw down their personnel and their hardware from Syria, there's nothing to stop the Israelis from striking Iranian assets with greater and greater impunity," Schanzer said. 

All this is bubbling as Biden prepares for his Middle East visit. The key stop in his itinerary is Saudi Arabia, where Biden will try to persuade Crown Prince Mohammed bin Sultan, the kingdom's de facto leader, to increase oil production in a bid to lower gas prices (and undercut Russian revenues). It will be an awkward moment for Biden, who as a candidate branded Prince Mohammed a "pariah" after the CIA determined he had ordered the grisly 2018 murder and dismemberment of Saudi dissident and Washington Post columnist Jamal Khashoggi in Istanbul. Biden also pledged to withdraw U.S. military and intelligence support for Saudi Arabia's devastating war in Yemen -- a promise that remains unfulfilled, according to a recent finding by The Washington Post. But with gas prices last clocked at $5 a gallon, realpolitik has trumped moral outrage. 

The president also will visit Israel, where talks will focus on the administration's effort to revive the stalled Iran nuclear deal. Chances of that are increasingly slim.

Israel, together with Saudi Arabia and the United Arab Emirates, have long opposed the deal. But unlike former Israeli Prime Minister Benjamin Netanyahu, who actively campaigned against it, Bennett has so far refrained from mobilizing Israel's U.S. lobbyists against the administration's policy, confident the negotiations will fail on their own. But as the recent military exercises and targeted killings demonstrate, he has repeatedly asserted Israel's right to defend itself against Iran, should the need arise. Meanwhile, Iran's act to remove 27 U.N. cameras monitoring its nuclear sites, reported Thursday, will only bolster the hand of Israeli hawks urging the government to take further preventative action.

For months, the Biden administration has told Israel its campaign of targeted killings will not dissuade U.S. officials from trying to reach a diplomatic solution to the Iranian nuclear issue. And for the first time, voices in Israel are urging the Mossad to halt the killings, calling them "pointless" and ineffective in halting Iran's nuclear program.

"This program is not dependent on one expert or a group of experts, even if they are nuclear physics geniuses," said the left-wing Israel daily Haaretz in an editorial earlier this week. "Anyone who believes that the ‘surgical' murder of a scientist will deter Iran is peddling a lie and saying, in effect, that the Iranian nuclear threat is a giant balloon that can be deflated with a single pinprick, or a bomb attached to a scientist's car."

"In fact, the assassinations that Israel carries out in a foreign country, even if that country is Iran, make it look like a neighborhood bully: a state that is driven by political struggles and whose government seeks to deflect criticism with the help of pointless intelligence antics, thereby endangering its citizens," the editorial continued. "These citizens deserve a convincing explanation as to why and how these killings serve Israel's interest." 

But for the time being, signs are the shadow war will go on -- and maybe even escalate, even as the war with Russia over Ukraine remains at center stage. As war-weary regional hands like to say, you can try to forget about the Middle East, but the Middle East never forgets about you.

This article by Jonathan Broder originally appeared on

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