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Russian President Vladimir Putin listens to a journalist's question after his annual call-in show in Moscow, Russia, on Thursday, June 20, 2019. Mr. Putin suggested that he had no plans to turn against Iran in exchange for concessions elsewhere.Alexander Zemlianichenko/The Associated Press

Russia and Iran have fought on the same side in Syria’s civil war, and are approaching victory there. Whether Moscow can now be persuaded to turn against its ally – and at what price – will be the topic of a gathering that begins Monday under heavy security in Jerusalem.

The unprecedented two-day meeting of the top Russian, American and Israeli security advisors – held amid skyrocketing tensions across the Middle East that have brought Washington and Tehran to the edge of military conflict – is a statement in itself to Iran. So, too, is its location in Jerusalem, a city that Iranian hard-liners regularly vow to one day “liberate” from the “Zionist regime.”

U.S. President Donald Trump says he approved a Friday morning wave of air strikes and missile attacks against Iranian targets – as punishment for the downing of an unmanned U.S. drone, which was shot out of the air over the Persian Gulf on Thursday – then abruptly decided against the military action. On the weekend, he called on Iran to return to the negotiating table in order to avoid further crippling economic sanctions and to “make Iran great again."

What happens next in this sensitive moment may be decided, in part, by the three-way security summit in Jerusalem. The United States and Israel view Iran as a region-wide menace – with the possibility of open conflict growing even before the drone incident, with the U.S. blaming Iran for recent attacks on oil tankers in the Persian Gulf – and will strive to convince Russia that Iran is a malicious actor. Moscow, if it agrees, is expected to demand major geopolitical concessions, in the Middle East and perhaps even in Ukraine, in exchange for any help pushing Iran and its allies out of Syria.

Israel, which is used to trading blows with the Iranian-backed Hezbollah militia in neighbouring Lebanon, views the presence of Iranian and pro-Iranian forces in Syria as an existential threat. John Bolton, the national security adviser to Mr. Trump, and Meir Ben-Shabbat, who holds the parallel post in the Israeli government, are expected to press the head of Russia’s national Security Council, Nikolai Patrushev, to use the military forces that Russia has deployed in Syria, as well as its influence over the regime of Bashar al-Assad, to drive Iran and its allied militias out of that country.

While Russia and Iran worked together to rescue Mr. al-Assad’s regime from what once seemed to be certain defeat, with Russia providing the air force and pro-Iran militias bolstering the Syrian army on the ground, there are signs the alliance of convenience is fraying as Moscow and Tehran diverge over the future of postwar Syria.

Moscow is believed to want a return to the prewar status quo, with Mr. al-Assad at the helm of a repressive regime that for decades launched rhetorical attacks on Israel but avoided military conflict. Iran, meanwhile, sees Syria as a key front against Israel but also in its region-wide struggle for influence against both the U.S. and a Sunni Muslim alliance headed by Saudi Arabia, and it has continued to build up its military presence in the country.

The Americans are also making preparations for conflict. The U.S. announced last week that it was sending an additional 1,000 troops to the Middle East after a June 13 attack on two oil tankers, the second such incident in less than a month. The U.S. force buildup follows an earlier deployment of 1,500 troops. The USS Abraham Lincoln aircraft carrier group has also been sent to the region, as has a bomber task force.

Tensions between the U.S. and Iran date back to Mr. Trump’s decision last year to pull the U.S. out of a multinational deal that was supposed to see Iran give up its nuclear ambitions in exchange for a lifting of economic sanctions. The Trump administration has reinstated penalties for any economic dealings with Iran, escalating the pressure on the country’s theocratic regime.

In televised remarks last week, Russian President Vladimir Putin warned that a war between the U.S. and Iran would be a “catastrophe” that could spark a fresh refugee crisis.

But the formidable air defence systems that Russia has deployed in Syria have stayed quiet as Israeli warplanes have repeatedly struck at Iran-linked targets inside Syria over the past 3½ years.

The question is what Mr. Putin would ask for in exchange for pushing Iran, one way or another, out of Syria – and how reliable any Kremlin promise would be.

Russia’s core interests in Syria are the stability of Mr. al-Assad’s regime and the preservation of its base in Tartus. Its alliance with Iran, meanwhile, is seen as less important than its need to escape the Western-led sanctions that were imposed in 2014 after Russia seized and annexed the Crimean Peninsula from Ukraine. Moscow would like to see the whole of Ukraine returned to what the Kremlin calls its “sphere of influence.”

Dan Shapiro, who served as U.S. ambassador to Israel under Barack Obama, called the Jerusalem meeting “a real opportunity to enlist the Russians in a more serious way” in the effort to curb Iran’s increasing influence in the region. Mr. Shapiro, however, worried that the Kremlin’s price tag would be something the U.S. shouldn’t be willing to pay.

“What worries me most is that the Russians will try to extract a Syria-for-Ukraine deal, with regards to increased Russian constraints on Iran in Syria in exchange for relief from Ukraine sanctions,” Mr. Shapiro said. “That’s a bad deal for U.S. interests, to call into question core European security needs in exchange for very questionable promises regarding [Russian] behaviour in the Middle East.”

The Jerusalem summit will likely also provide the U.S. with an opportunity to brief Mr. Patrushev on Mr. Trump’s stumbling plan to forge a peace deal between Israel and the Palestinians, who have lived under Israeli military occupation since 1967. The Jerusalem meeting opens one day before Mr. Trump’s son-in-law, Jared Kushner, presides over a gathering of Arab business leaders in the Gulf kingdom of Bahrain, where Mr. Kushner is expected to try and drum up support, and economic commitments, for the White House plan.

Iran, so far, has responded to the Jerusalem summit largely by ignoring it, giving it almost no attention in state media. Ali Asghar Khaji, an official in Iran’s Foreign Ministry, told Russia’s Sputnik news service that Iran was “confident that the Russian government will take a principled position, will not succumb to the excessive desires of the United States and Israel, and will not follow them.”

In his televised remarks, Mr. Putin suggested he had no plans to turn against Iran in exchange for concessions elsewhere. “What do you mean ‘a grand deal'?" he said in reply to a question from a journalist. "Sounds like some commercial act. No. We don’t sell out our allies, our interests or our principles.” Mr. Putin added, however, that he hoped there was sufficient “goodwill” to reach an understanding on Syria’s future.

Dore Gold, a retired diplomat who served as foreign affairs adviser to Israeli Prime Minister Benjamin Netanyahu and later as head of Israel’s Foreign Ministry, said Russia’s presence at the Jerusalem summit was testament to the clout Moscow had gained in the region in the four years since Mr. Putin sent troops and warplanes to save Mr. al-Assad’s collapsing regime.

“President Putin has succeeded in restoring much of the stature of the Soviet Union here in the Middle East … he’s got the power in his hands.” The question now, Mr. Gold said, was what Mr. Putin intended to do with that power.