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What Obama Owes Putin—and Why Donald Trump Is Left Holding the Bag

Broader aims on Middle East realignment led the outgoing president’s efforts at two-track diplomacy. One track was misdirection. The other handed the region to Russia and Iran.

Lee Smith
January 17, 2017
Photo: Jewel Samad/AFP/Getty Images
Photo: Jewel Samad/AFP/Getty Images
Photo: Jewel Samad/AFP/Getty Images
Photo: Jewel Samad/AFP/Getty Images

Is Donald Trump a Russian secret agent? Did he pay FSB hookers to pee on the bed the Obamas slept in at the Ritz in Moscow, overlooking the Kremlin? It’s silly season, so any drunk on a fat oppo-research expense account can write down any crazy foolishness they want and Buzzfeed will let you decide if it’s true because that, as Buzzfeed’s editor, Ben Smith, solemnly explained to The New York Times, is where American journalism is at in 2017. Duly noted, Buzzfeed. Enjoy the golden showers.

What’s being obscured by this grotesquerie is the origin and the actual substance of U.S. foreign policy toward Russia, which in turn affects the lives of hundreds of millions of people living in Syria, Iraq, Ukraine, and elsewhere. Or, to put it another way: Is Donald Trump likely to continue the policies of his predecessor, which set the Middle East on fire and led to 500,000 deaths in Syria, and to Putin biting off large chunks of the sovereign nation of Ukraine? Or is he likely to reverse those policies? Or can he, even if he wanted to?

The single-mindedness with which the White House and the remnants of the Clinton campaign have pursued the idea that Donald Trump is a pawn of Vladimir Putin is not based on silly stories about peeing prostitutes or secret computer servers that connect the Trump organization to the Kremlin. Rather, it’s an attempt to manufacture more smoke to obscure the reality of Obama’s own determination to collaborate with a hostile Russian leader in Syria, and elsewhere in the Middle East.

Sure, Obama recently sent 35 Russian diplomats packing and shuttered Russian diplomatic facilities in Maryland and New York, but this was after seven years of looking the other way while Russia seized Crimea, then Donbass; waged cyberattacks on the Baltic countries; brought down a passenger jet over Ukraine; sheltered Edward Snowden; and bombed schools and hospitals in Syria. All of these actions threatened global stability and American interests, yet Obama only puffed his chest after the cyberattacks on the Democratic National Committee and Clinton Campaign Chairman John Podesta’s emails—long after it mattered, and after the moving vans have already started to haul his stuff out of the White House.

The reason top national-security journalists, policy mandarins, and much of the Washington establishment can’t fathom Obama’s relationship with Putin is only partly due to partisanship. The real reason it’s so hard to see how much room the outgoing president gave Putin is because misdirection has been Obama’s guiding principle for seven years.

The president made it look like he was at odds with Putin for much of his two terms—for instance, loudly poo-pooing the Russian campaign in Syria and warning of Vietnam-style “quagmires,” dismissing Russia as a weak country, sending an LGBT delegation to the Sochi Olympics to underscore his differences with Russia’s treatment of the LGBT community. All this helped obscure the fact that when it really counted, Obama took special care to signal the Russian strongman that their interests were aligned. That wasn’t because he has a man-crush on Putin, but because he had a larger purpose in view—securing the Iran nuclear deal.

The point isn’t that Obama lied. Sure, he lied. All politicians lie all the time, right and left, Republican and Democrat. All governments lie, perhaps especially liberal democracies, which don’t have the luxury afforded authoritarian regimes to do whatever they want at no cost to their approval ratings, which hardly matter. Liberal democracies lie especially when they’re crafting policies that would make many of their constituents queasy.

For two terms the Obama White House staged a foreign-policy puppet show, while the real drama took place far from the spotlight—a mutant variation of dual-track diplomacy. Policy is often conducted along two tracks—maybe military and diplomatic, or hard power and soft power, like development assistance or cultural-exchange programs. Diplomacy is almost always conducted on two tracks. Track-two diplomacy is a term of art that refers to the nonofficial meetings held by private individuals or groups that give the official parties the nonofficials represent enough room to disclaim ownership if or when it blows up. The Oslo peace process began as track-two diplomacy, for example, as have plenty of other major diplomatic initiatives. The point is that whether we’re talking about foreign aid or political pressure, military force or moral suasion, the two tracks of dual-track diplomacy are almost always pointed in the same general direction, with the aim of securing the same outcome.

The Obama administration’s dual-track diplomacy was different because the public track was intended to cover for the real show going on behind the scenes. For instance, if it looked like Obama was at odds with Putin over Russia’s destructive escalation in Syria and its role in crushing the rebels and killing civilians, nothing could have been further from the truth. Yet Obama needed Putin to rescue Iran and save its regional position. So while Obama was denouncing Putin in public, his White House errand boys were actually meeting in private with Putin’s errand boys, helping the Russians to accomplish the very things that the administration—especially the State Department—then publicly denounced. On bad days, it could look like there were actually two U.S. governments, pursuing policies that were diametrically opposed to each other. In fact, there was only one government, led by Obama—and the policy of that government was entirely coherent, although not necessarily wise.

For what mattered most to Obama wasn’t Syria, nor even was it the Joint Comprehensive Plan of Action, which is typically referred to as Obama’s signature foreign-policy initiative. Even that was a feint, cover for a larger strategy that entailed a realignment of interests in the Middle East and a new form of foreign-policy “realism” that would get American troops out of the Middle East—and put America in the same column as Iran and its allies, including Vladimir Putin.

Yes, as Obama believed, Americans were sick of the problems and psychoses of the Middle East, and angry that George W. Bush failed to win his two Middle East wars. But neither Congress nor the U.S. foreign-policy establishment was keen to see the United States dismantle a regional security architecture it took 70 years to build, and which Obama and his young aides saw as a guarantee of future friction, and future U.S. military engagement. Someone needed to smash that architecture with a hammer.

So the Obama White House made stuff up. No one wanted to side with Iran and downgrade traditional allies like Israel. And so the Obama administration said that wasn’t happening. And the way it obscured the truth was to stage a dog-and-pony show with familiar Beltway names and faces to keep the Buzzfeed kids busy pondering the complexities of U.S. foreign policy while the adults went about their deadly serious business. What looked like the president of the United States pulling a rabbit out of his hat was actually Obama sawing a woman in half—and drawing blood.


Is that really what happened? Some former Obama officials, like the administration’s onetime Syria point man, Frederic Hof, argue that the reason the administration’s foreign policy is a mess is because the president and his men in the White House lacked experience in the federal bureaucracy. In this view, the Obama team—namely, National Security Adviser Susan Rice—didn’t know how to manage what people in the know call the “interagency process,” or how the various institutions, like the National Security Council staff, State Department, Pentagon, and intelligence community process policy.

The reality is that Obama and his closest aides were contemptuous of the institutions, staffed by those very same Beltway bureaucrats that collectively make up what Obama deputy Ben Rhodes disparagingly called “The Blob.” As both Obama and Rhodes have explained, the mediocrities worthy of contempt included members of Obama’s cabinet. The reason for tapping figures like Leon Panetta, Robert Gates, David Petraeus, Hillary Clinton, John Kerry, and Samantha Power was to use the establishment as cover, while the real players, like Obama and Rhodes, Rob Malley, and a few select others, maneuvered in the shadows, and spun covering fictions. By 2012, as Gates and Panetta detailed in their memoirs, the Wise Men came to understand they were simply pawns in the president’s larger game, and quit before the real bloodshed started.

Hillary Clinton, with an eye to her presidential campaign, was not about to cross Obama in public, as Gates, Panetta, Chuck Hagel, and others did, but she knew she was window dressing, too. Her State Department was surprised when John Kerry, then head of the Senate Foreign Relations Committee, was tasked to open a channel with the Iranians through Oman. The concessions Kerry offered Iran, especially the right to enrich uranium, angered Clinton’s staff. Kerry was screwing up badly, they leaked to reliable press contacts, they’d never have blundered like that.

Was the Clinton team really shocked and outraged? No, it was just cranking up its own fog machine, lest anyone realize the White House had done the worst thing anyone can do to someone else in Washington—make them irrelevant. Hillary Clinton’s job wasn’t to make policy—it was to rack up frequent-flier miles and stay out of the way while the White House handled the big-ticket items like Israel, Iran, China, and every other issue of any major importance. Nor did she particularly want the responsibility for decisions that she and her coterie may have opposed, and which certainly were likely to anger many of her prominent traditional liberal supporters. “The president,” as one official from a pro-Israel organization in Washington told me, “leapfrogged the State Department.”

Clinton’s successor, John Kerry, was either less ambitious or more vain than Clinton, or maybe both. He was the electronic rabbit while the real work of shaping the world was done by much younger men who represented the will of the president of the United States. What Kerry did in public, all those marathon negotiating sessions, all those windy speeches, was a sideshow. The fact that his tremendous vanity made him think that it was real only added conviction to his performance—all the better to generate buzz among 27-year-old reporters at Buzzfeed and their instant-foreign-policy-expert buddies at the newly-minted Washington “think tanks” led by Democratic political operatives like Neera Tanden, whose actual experience of any particular part of the world or area of human endeavor—warfare, diplomacy, nuclear engineering, you name it—was nil.

So while Buzzfeed—and the New Yorker—wrote articles about how John Kerry was manfully negotiating cease-fires in Syria with his Russian counterpart, Sergei Lavrov, it was, in fact, Obama’s own Middle East point man, Robert Malley, who conveyed the president’s real policy. Almost as soon as Obama called for Assad to step aside in August 2011, the administration came to regret that bit of grandstanding, and walked it back. As Tony Badran, a research fellow at the Foundation for the Defense of Democracies told me, “The administration went from ‘transitioning away from Assad’ to ‘de-escalating’ the conflict, or stopping the bloodshed. The White House used a veneer of humanitarian concern to elide the fact that removing Assad was no longer a part of the equation. It was now about shutting down the war against Assad.”

It wasn’t long before foreign officials came to understand that Obama was working two seemingly opposing channels—the trick was figuring out which channel was real. As a source close to the Turkish government explained to me, Turkey’s former prime minister, Ahmet Davutoglu, eventually concluded that Obama was using Clinton as a prop. Whatever promises she might make on Syria, for instance, were worthless. They were also often actively misleading, as they were unconnected to what the Americans were actually doing on the ground. The White House had sent its top diplomat out to lie, and without informing her she was lying.

No one saw more of the administration’s shell game than Israel. The White House reassured Jerusalem that it wasn’t going to sell Iran the farm—Israel was their ally, and Iran was the enemy. As one former senior U.S. official told me, “The Bush administration and Israel had developed a pressure track on Iran, primarily through the intelligence community. This was the track that produced Stuxnet. But Obama shut down the pressure track with the opening of the Oman channel since they didn’t believe that pressure and diplomacy work together. But the Obama White House couldn’t tell the Israelis they were shutting down the pressure track. So the president wrapped them up in planning, promising, for instance, a Stuxnet 2.0. So you have emissaries going back and forth, planning and planning and planning, which was actually just stalling.”

Moreover, said the former U.S. official, the Israelis knew that Obama was lying about the Oman channel. He added that the head of the U.S. team negotiating with Iran, Wendy Sherman, “would meet openly with the Iranians as part of the P5+1 talks, then fly to Jerusalem, and tell the Israelis, ‘We got your back.’ But the Israelis knew the Americans were meeting with Iran because they had the tail numbers of planes going to Oman. The Israelis went to Obama’s then national security adviser, Thomas Donilon, and said, ‘We know what’s going on.’ ”

In fact, the Israelis didn’t understand. They thought, like most critics of the Iran deal, that the administration was just flubbing negotiations and needed help. But the White House didn’t care that much about the particulars because the JCPOA was simply a device to allow for a larger, even more historic play—Obama wanted to get America out of the Middle East, and realigning with Iran was America’s exit strategy.

For the big problem with the region, from Obama’s perspective, is the lure of the “Washington playbook,” a set of guiding principles that typically point to the use of force, which was passed down by generations of government grandees—the kind he used as rodeo clowns. The question was: How could Obama cover America’s retreat, yet ensure a certain amount of stability in the Middle East? Israel was too small for the role of regional policeman, and besides, its policies toward the Palestinians pointed toward instability. The Sunni Arab states were fractious and incapable of working together, and their own internal problems gave rise to extremism. That left Iran.

Clearly, there are plenty of Obama administration officials enamored with the Islamic Republic, whether they’re attracted to the vintage patina of late 20th-century Third Worldism or classic Persian culture. What was most appealing to Obama, as he told a meeting of Gulf Arab officials at Camp David in 2015, was simply that the Iranians are capable of getting things done—a sentiment that he expressed in the context of his admiration for the Revolutionary Guards Corps’ expeditionary unit led by Qassem Soleimani. However, he also realized that this conviction and the policy it undergirded would have grossed out a large number, likely a majority, of Americans, and their elected representatives. So he lied, or misled and misdirected—and said the JCPOA was about stopping Iran from getting a nuclear weapon, and nothing more.


All the major foreign-policy issues of the Obama presidency (the fraying of the bilateral relationship with Israel, the withdrawal from Iraq, Russia, etc.) were subsets of realignment policy—including the administration’s management of the single largest strategic, political, and humanitarian catastrophe of the 21st century, the Syrian conflict. Obama’s cabinet held the mainstream view of the Syrian war—Panetta, Clinton, Kerry, Petraeus, and Power all supported arming the rebels to defeat Assad, or at least compel him to negotiate under harder circumstances. But that was exactly the opposite of what Obama wanted to do.

A more hawkish position was expressed by the U.S. officials like then-head of CENTCOM and now Trump’s nominee for defense secretary, Gen. James Mattis, who thought crushing Assad would be a huge strategic setback for Iran. And that’s just what worried Obama, who hardly needed the Iranians to warn him that realignment would collapse if America targeted the Syrian regime. After all, realignment was predicated on the idea of a strong Iran with a can-do Quds Force that could act as the region’s new policeman. An Iran knocked back down to size, and where the country’s internal opposition would be emboldened, would be of no use to a White House keen to hand over the keys to the Middle East and get out. Obama needed a big Iran, a “successful regional power,” as he’s put it.

A victory for the Syrian opposition—whom the White House could not help but disparage even as the president and his aides honored the victims of Assad’s depredations, i.e., the opposition—would have been a disaster for the Obama administration. It would have not only cashiered Obama’s hopes for a hegemonic Iran capable of managing American regional interests but would have required Washington to manage the varied and often conflicting interests of its regional allies, Israel, Jordan, Saudi Arabia, Turkey, etc. In other words, an opposition victory would have demanded more American involvement in the Middle East—more time, attention, energy, money, and perhaps blood.

The structural problem with Obama’s grand realignment is that Iran simply can’t handle the load. Obama should have understood this every time he had to tip the scales on behalf of the Iranians. When the administration leaked that Israel struck Iranian arms convoys headed to Hezbollah, Obama should’ve understood that he was tipping the scales, but it still wasn’t working. Qassem Suleimani turned out to be less than impressive, for his Quds Force couldn’t even tackle ISIS without the U.S. providing air support in Tikrit. The much-heralded operation to take back Mosul before Obama left office is such a mess that the White House simply doesn’t talk about it anymore.

When the Russians escalated in Syria in September 2015, Obama should have seen it as a clear sign he’d been wrong about Iran: The IRGC couldn’t even put down the farmers and carpenters the American president repeatedly disparaged. They needed the Russians to do it for them.

The White House said Putin’s action caught them by surprise, but that is unlikely to be true. The Russians were moving men and materiel for months through the Bosphorus—under the control of NATO member Turkey—at least since Suleimani’s July 2015 trip to Moscow to ask for Russian intervention.

The reality is that the Russian campaign in Syria served vital Obama interests. There was no point in realigning with Iran if Tehran’s regional position collapsed. Putin saved not only Assad and Iran, but Obama’s realignment policy. It was the second time the Russian president rescued Obama’s realignment policy—the first being when he offered the deal over Assad’s chemical weapons that allowed the commander-in-chief to walk back his red line.

Obama owes Putin, which is why he let the Russians get away with nearly everything it chose to do the last seven years, including its attacks on the American political system. What’s left for Trump is to manage the Russia policy he inherited from Obama—or overturn the table.