Putin's Iran-Israel dilemma amid growing fears of regional war: 'Complex considerations'

As the crisis in the Middle East continues to escalate amid concerns of an anticipated Iranian attack on Israel in retaliation for the killing of Ismail Haniyeh last week in Tehran, Russian President Vladimir Putin advised Iran's supreme leader, Ayatollah Ali Khamenei, to avoid Israeli civilian casualties. This message was delivered by Russia’s Security Council Secretary Sergei Shoigu, who met with Iranian leaders including President Masoud Pezeshkian, on Monday in Tehran. 

Now, why would the Russian "murderous dictator," as President Biden once called Putin, do this at the time when the Pentagon is boosting its military presence in the Middle East in preparation for what Secretary of State Antony Blinken termed as an "imminent" attack on Israel by Iran and Hezbollah? 

The worst-case scenario that many national security professionals are now worried about is a broader war in the Middle East. And if that happens, the big question is: Would Russia, the world’s largest nuclear power and a top U.S. antagonist, align itself with Iran? Because if it did, it would have catastrophic consequences for the region and the world.

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There’s an assumption now in Washington that Putin would automatically side with Tehran and against Israel and the United States. After all, Iran has been providing Moscow with hundreds of ballistic missiles, drones and other munitions to fight against Ukraine. The U.S., on the other hand, has been flowing advanced weapons and cash to Ukraine to help degrade the Russian military.

Russian President Vladimir Putin, left, greets Israeli Prime Minister Benjamin Netanyahu during their meeting in Sochi, Russia, on Sept. 12, 2019. (Mikhail Svetlov/Getty Images)

But Putin’s decision calculus is not simple. His relationship with Israel and Tehran is not linear, but rather it's driven by complex considerations. Here’s why Putin almost certainly doesn’t want a devastating strike on Israel. 

Throughout his presidency and until the invasion of Ukraine, Putin has pursued a largely pro-Israel policy. Not because he is a nice guy, but because he is a pragmatist. Since becoming president in 2000, Putin has drastically improved the Russian-Israeli relationship. After decades of hostile relations between the USSR and Israel, Putin became the first Kremlin leader to visit Israel in 2005. He subsequently endorsed the building of a massive $60 million Jewish Museum and Tolerance Center, to which he donated a month’s worth of his salary. Having opened in Moscow in 2012, the museum acknowledged Russia’s and the USSR’s history of antisemitism and recognized the contributions of Jews to Soviet life. 

As a practical matter, Putin likely calculates that the 1.2 million Russian and former Soviet émigrés living in Israel represent a good pool of expatriates who could return to their own or their parents’ motherland, adding some educated human capital to demographically struggling Russia. He also sees Jewish émigrés in Israel, Europe and the United States as a potential source of investment in Russia, especially in high technology, now that Russia is marginalized from the West because of its war on Ukraine. 

Russian President Vladimir Putin, left, meets with Iranian Supreme Leader Ayatollah Ali Khamenei. (Dmitry Azarov/Sputnik/AFP via Getty Images/File)

Putin frequently meets with the Chief Rabbi of Russia Berel Lazar. They write joint holiday greetings to the Jewish people in Russia. Putin sometimes repeats the jokes that Lazar tells him. When speaking about the Russian-speaking Israeli population, Putin calls them "our Jews" ("Nashi Yevrei").

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Moreover, Putin probably sees an opportunity to influence the politics of the Jewish state as Israel has become home to the world’s largest population of Jews from the former Soviet Union, with 15%-17% of the Israeli population being Russian-speaking. 

Putin used to have an excellent relationship with Prime Minister Benjamin Netanyahu, who views the Russian émigré population as key to his political success and survival. Indeed, Jewish immigrants and their descendants have become a sizable secular nationalist political block, which has secured right-wing rule to this day. During his 2019 electoral campaign, Netanyahu placed ads and billboards in Russian, highlighting his ties with Putin, and increased the number of Russian-language media interviews in hopes of getting Russian-Israelis’ votes.

Iranians follow a truck carrying the coffins of Hamas leader Ismail Haniyeh and his bodyguard during their funeral ceremony in Tehran, Iran, on Aug. 1, 2024. (AP/Vahid Salemi)

The personal rapport between Putin and Netanyahu, both realpolitik-minded and pragmatic, strengthened the Russian-Israeli relationship. The two leaders share the belief that Islamic extremism is a common enemy with which there cannot be a compromise. Notably, Israel did not criticize Moscow for its wars in Muslim Chechnya nor did it express any negative reaction to Putin’s annexation of Crimea. 

In fact, Israel studiously maintained a neutral posture during the initial stages of the Russia-Ukraine conflict, having refrained from condemning Putin for the invasion, refused to join the U.S. and EU sanctions against Moscow, and opted to provide only humanitarian aid to Ukraine rather than military hardware. This was a strategic decision by Israel, which viewed Russia as a new power broker in the region critical to its ability to manage the threat from Iran. Risking Washington’s ire, Israel prioritized the critically needed security coordination between the Russian military and Israel Defense Forces in Syria, where Russia controls the skies and has tacitly allowed Israeli fighter jets to conduct strikes on Iranian proxies.

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Russian President Vladimir Putin, center, and Chief Rabbi of Russia Berel Lazar, right, attend a ceremony unveiling the memorial for members of the resistance in Nazi concentration camps during World War II at the Jewish Museum and Tolerance Center in Moscow on June 4, 2019. (Sergei Ilnitsky/AFP via Getty Images)

Moscow was not always a friend of the ayatollahs either, having shared a tumultuous history with Tehran. In 2010, the Kremlin – obeying U.N. sanctions – banned by a presidential decree the sale to Iran of S-300 air defense missile system, which would have augmented the defenses of Iranian nuclear sites from airstrikes. And in 2019, amid rising tensions in the Persian Gulf, Putin declined Iran’s request to buy the advanced S-400 missile defense system. This was probably in response to concerns shared by Israel and Saudi Arabia and because he sought to maintain a positive working relationship with the two. 

The Biden administration, however, has driven a wedge between Moscow and Jerusalem, pushing Russia and Iran closer than ever. Under relentless pressure, Washington compelled Israel to supply military hardware to Ukraine to fight against Russia. 

Putin is highly unlikely to risk losing all of this political and personal capital he built with Russian-Israeli Jews and the state of Israel over the course of almost a quarter of a century, and alienating Saudi Arabia, by letting himself be perceived as enabling Iran to strike Israel.

An Israeli election billboard showing Likud chair and Prime Minister Benjamin Netanyahu with a caption in Russian reading, "Only Likud, only Netanyahu," is displayed in Jerusalem on Sept. 14, 2019.

Publicly, Moscow will almost certainly maintain pro-Iran and anti-Western rhetoric, however, aiming to keep Iran on its side and to boost its negotiating leverage with the United States over Ukraine and Western economic sanctions. Putin seeks to show the U.S. and the world that he can be dealt with on a transactional basis.

The recent massive prisoner exchange with the U.S. and several European countries is a clear example of that. The prisoner swap took place even as Ukraine was finally receiving U.S. F-16s, which will be killing Russian forces. On Friday, Putin also withdrew at the last minute the delivery of weaponry to Houthi rebels in Yemen, also probably to show to Saudi Arabia and the U.S. that Moscow, while in a marriage of convenience with Tehran, is not seeking a World War III.

The rhetoric coming out of the Biden administration about Putin and Russia – like "son of a b---h," "murderous dictator" and "gas station masquerading as a country" – reveals that emotions rather than rational calculus are driving Washington’s policies. This incompetent and childish approach to statecraft has set the world on fire.

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As November is getting ever closer, Americans must decide which team – Trump or Harris – has the intellectual firepower, competence and nuanced understanding of the world to ensure America’s and its true allies’ security first.

Putin may be a killer and a dictator, but he is realpolitik to the core, skillfully playing a geopolitical game of chess. His decision calculus is not irrational. To outplay him, any U.S. leader must understand the Russian spymaster’s thinking first.

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