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As the Trump administration begins planning its outreach to Moscow, one question for the new president will be whether he can persuade Russia to turn away from Iran.

The two countries have grown closer since 2015, when a group of nations lifted some sanctions on Iran in exchange for more transparency about its nuclear program. Russia sells Iran advanced air defense systems, and Iran provides its officers and militias to conquer the Syrian towns and cities indiscriminately bombed by Russian aircraft.

Trump administration officials tell me that they will explore the extent to which Russian President Vladimir Putin wants to end this relationship and cooperate with U.S. policy to counter Iranian aggression in Syria and the Middle East.

"It's important to find out what are the limits of Russia's willingness to cooperate with us with regard to Iran," said Michael Ledeen, who during the transition served as an adviser to Michael Flynn, now Trump's national security adviser. "Those conversations have to take place." Ledeen was Flynn's co-author of "Field of Fight," a 2016 book that outlined the retired general's national security vision.

That book makes the case that Iran must be defeated in order to win the war against radical Islam. At the same time, Flynn and Ledeen are also critical of Russia's value as a partner in the war against the Islamic State. "When it is said that Russia would make an ideal partner for fighting Radical Islam, it behooves us to remember that the Russians haven't been very effective at fighting jihadis on their own territory, and are in cahoots with the Iranians," they wrote. "In Syria, the two allies have loudly proclaimed they are waging war against ISIS, but in reality the great bulk of their efforts are aimed at the opponents of the Assad regime."

Now a great bulk of the Trump administration's diplomatic efforts will be to persuade Russia to cut the Iranians loose in Syria and to end arms sales to the Islamic Republic. Another factor will be the Iran nuclear agreement negotiated by Trump's predecessor. Trump has said he will not withdraw right away from it. But he has also been critical of the deal, and some incoming officials have said they would like to see if it's possible to renegotiate better terms.

In this sense, Trump is hewing closely to Barack Obama's playbook when he came into office in 2009. Back then, the U.S. scrapped a missile defense deployment in the Czech Republic and Poland and did not further pressure Russia on its occupation of Georgian territory following the 2008 war. In exchange, the Russians supported a U.N. Security Council resolution against Iran's nuclear program and negotiated an arms control treaty limiting long-range nuclear weapons for both countries.

It's unclear what the Russians would want in return this time around. Michael McFaul, a former U.S. ambassador to Russia who was an architect of Obama's first-term outreach to Russia, told me he didn't know what Trump could offer Putin in exchange for abandoning Iran, a key ally and trading partner. "Are we going to buy Russianweapons systems that Moscow can now sell to Tehran? Of course not," he said. "Are we going to get our Sunni allies to do so? That seems unlikely.I just don't see what Putin has to gain from such a deal."

Putin has at times hinted at what he'd like from the U.S. Before the election, the Kremlin announced it was suspending an agreement to dispose of weapons-grade plutonium in October. The Kremlin's announcement said Russia would consider renewing the plutonium agreement if the U.S. reduced its military presence in NATO countries along its borders, canceled sanctions imposed after Russia's annexation of Crimea and compensated Russia for revenue it lost because of those sanctions.

Trump himself has not said specifically what he would be willing to offer the Russians, though he has said he would be willing to lift sanctions on Russia under the right circumstances and has said in interviews that he is interested in pursuing new arms-control agreements with Russia.

Either way, the Iranian problem remains. Matthew McInnis, a former Defense Intelligence Agency analyst on Iran who is now a resident fellow at the American Enterprise Institute, told me: "I see absolutely no way that you drive the Iranians out of Syria. But I could see how you reduce Iranian influence and presence there. That is a goal they could pursue." McInnis said this would mean Russia agrees to support rebuilding a Syrian army that would not be under the sway of Iran and its foreign militias.

Trump could also use the opportunity to play mind games with Iran's notoriously paranoid leaders. The Romanovs humiliated Iran in the 19th century with punitive treaties. Last summer tensions rose briefly when the Russians acknowledged they were flying air missions out of Iran into Syria. Iranian mistrust of Russia can be exploited with deft diplomacy.

It will be a balancing act. Trump will have a hard time persuading Congress that any accommodation of Russia these days is worth it, particularly because the intelligence community is now investigating ties between Trump's campaign and Putin's government before the election. Meanwhile Russia will have to weigh whether it values a new friendship with America over the one it already has with Iran.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

To contact the author of this story: Eli Lake at elake1@bloomberg.net

To contact the editor responsible for this story: Philip Gray at philipgray@bloomberg.net

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Trump Team Aims to Test Russia's Alliance With Iran - Bloomberg