One day in January, in Kerry’s office at the State Department, I expressed the obvious: He has more of a bias toward action than the president does.

“I do, probably,” Kerry acknowledged. “Look, the final say on these things is in his hands … I’d say that I think we’ve had a very symbiotic, synergistic, whatever you call it, relationship, which works very effectively. Because I’ll come in with the bias toward ‘Let’s try to do this, let’s try to do that, let’s get this done.’ ”

Obama’s caution on Syria has vexed those in the administration who have seen opportunities, at different moments over the past four years, to tilt the battlefield against Assad. Some thought that Putin’s decision to fight on behalf of Assad would prompt Obama to intensify American efforts to help anti-regime rebels. But Obama, at least as of this writing, would not be moved, in part because he believed that it was not his business to stop Russia from making what he thought was a terrible mistake. “They are overextended. They’re bleeding,” he told me. “And their economy has contracted for three years in a row, drastically.”

Obama meets with Jordan’s King Abdullah II at the White House in February of 2015. (Kevin Lamarque / Reuters)

In recent National Security Council meetings, Obama’s strategy was occasionally referred to as the “Tom Sawyer approach.” Obama’s view was that if Putin wanted to expend his regime’s resources by painting the fence in Syria, the U.S. should let him. By late winter, though, when it appeared that Russia was making advances in its campaign to solidify Assad’s rule, the White House began discussing ways to deepen support for the rebels, though the president’s ambivalence about more-extensive engagement remained. In conversations I had with National Security Council officials over the past couple of months, I sensed a foreboding that an event—another San Bernardino–style attack, for instance—would compel the United States to take new and direct action in Syria. For Obama, this would be a nightmare.

If there had been no Iraq, no Afghanistan, and no Libya, Obama told me, he might be more apt to take risks in Syria. “A president does not make decisions in a vacuum. He does not have a blank slate. Any president who was thoughtful, I believe, would recognize that after over a decade of war, with obligations that are still to this day requiring great amounts of resources and attention in Afghanistan, with the experience of Iraq, with the strains that it’s placed on our military—any thoughtful president would hesitate about making a renewed commitment in the exact same region of the world with some of the exact same dynamics and the same probability of an unsatisfactory outcome.”

Are you too cautious?, I asked.

“No,” he said. “Do I think that had we not invaded Iraq and were we not still involved in sending billions of dollars and a number of military trainers and advisers into Afghanistan, would I potentially have thought about taking on some additional risk to help try to shape the Syria situation? I don’t know.”

What has struck me is that, even as his secretary of state warns about a dire, Syria-fueled European apocalypse, Obama has not recategorized the country’s civil war as a top-tier security threat.

Obama’s hesitation to join the battle for Syria is held out as proof by his critics that he is too naive; his decision in 2013 not to fire missiles is proof, they argue, that he is a bluffer.

This critique frustrates the president. “Nobody remembers bin Laden anymore,” he says. “Nobody talks about me ordering 30,000 more troops into Afghanistan.” The red-line crisis, he said, “is the point of the inverted pyramid upon which all other theories rest.”

One afternoon in late January, as I was leaving the Oval Office, I mentioned to Obama a moment from an interview in 2012 when he told me that he would not allow Iran to gain possession of a nuclear weapon. “You said, ‘I’m the president of the United States, I don’t bluff.’ ”

He said, “I don’t.”

Shortly after that interview four years ago, Ehud Barak, who was then the defense minister of Israel, asked me whether I thought Obama’s no-bluff promise was itself a bluff. I answered that I found it difficult to imagine that the leader of the United States would bluff about something so consequential. But Barak’s question had stayed with me. So as I stood in the doorway with the president, I asked: “Was it a bluff?” I told him that few people now believe he actually would have attacked Iran to keep it from getting a nuclear weapon.

“That’s interesting,” he said, noncommittally.

I started to talk: “Do you—”

He interrupted. “I actually would have,” he said, meaning that he would have struck Iran’s nuclear facilities. “If I saw them break out.”

He added, “Now, the argument that can’t be resolved, because it’s entirely situational, was what constitutes them getting” the bomb. “This was the argument I was having with Bibi Netanyahu.” Netanyahu wanted Obama to prevent Iran from being capable of building a bomb, not merely from possessing a bomb.

“You were right to believe it,” the president said. And then he made his key point. “This was in the category of an American interest.”

I was reminded then of something Derek Chollet, a former National Security Council official, told me: “Obama is a gambler, not a bluffer.”

Ruven Afanador

The president has placed some huge bets. Last May, as he was trying to move the Iran nuclear deal through Congress, I told him that the agreement was making me nervous. His response was telling. “Look, 20 years from now, I’m still going to be around, God willing. If Iran has a nuclear weapon, it’s my name on this,” he said. “I think it’s fair to say that in addition to our profound national-security interests, I have a personal interest in locking this down.”

In the matter of the Syrian regime and its Iranian and Russian sponsors, Obama has bet, and seems prepared to continue betting, that the price of direct U.S. action would be higher than the price of inaction. And he is sanguine enough to live with the perilous ambiguities of his decisions. Though in his Nobel Peace Prize speech in 2009, Obama said, “Inaction tears at our conscience and can lead to more costly intervention later,” today the opinions of humanitarian interventionists do not seem to move him, at least not publicly. He undoubtedly knows that a next-generation Samantha Power will write critically of his unwillingness to do more to prevent the continuing slaughter in Syria. (For that matter, Samantha Power will also be the subject of criticism from the next Samantha Power.) As he comes to the end of his presidency, Obama believes he has done his country a large favor by keeping it out of the maelstrom—and he believes, I suspect, that historians will one day judge him wise for having done so.

Inside the West Wing, officials say that Obama, as a president who inherited a financial crisis and two active wars from his predecessor, is keen to leave “a clean barn” to whoever succeeds him. This is why the fight against isis, a group he considers to be a direct, though not existential, threat to the U.S., is his most urgent priority for the remainder of his presidency; killing the so-called caliph of the Islamic State, Abu Bakr al-Baghdadi, is one of the top goals of the American national-security apparatus in Obama’s last year.

Of course, isis was midwifed into existence, in part, by the Assad regime. Yet by Obama’s stringent standards, Assad’s continued rule for the moment still doesn’t rise to the level of direct challenge to America’s national security.

This is what is so controversial about the president’s approach, and what will be controversial for years to come—the standard he has used to define what, exactly, constitutes a direct threat.

Obama has come to a number of dovetailing conclusions about the world, and about America’s role in it. The first is that the Middle East is no longer terribly important to American interests. The second is that even if the Middle East were surpassingly important, there would still be little an American president could do to make it a better place. The third is that the innate American desire to fix the sorts of problems that manifest themselves most drastically in the Middle East inevitably leads to warfare, to the deaths of U.S. soldiers, and to the eventual hemorrhaging of U.S. credibility and power. The fourth is that the world cannot afford to see the diminishment of U.S. power. Just as the leaders of several American allies have found Obama’s leadership inadequate to the tasks before him, he himself has found world leadership wanting: global partners who often lack the vision and the will to spend political capital in pursuit of broad, progressive goals, and adversaries who are not, in his mind, as rational as he is. Obama believes that history has sides, and that America’s adversaries—and some of its putative allies—have situated themselves on the wrong one, a place where tribalism, fundamentalism, sectarianism, and militarism still flourish. What they don’t understand is that history is bending in his direction.

“The central argument is that by keeping America from immersing itself in the crises of the Middle East, the foreign-policy establishment believes that the president is precipitating our decline,” Ben Rhodes told me. “But the president himself takes the opposite view, which is that overextension in the Middle East will ultimately harm our economy, harm our ability to look for other opportunities and to deal with other challenges, and, most important, endanger the lives of American service members for reasons that are not in the direct American national-security interest.”

If you are a supporter of the president, his strategy makes eminent sense: Double down in those parts of the world where success is plausible, and limit America’s exposure to the rest. His critics believe, however, that problems like those presented by the Middle East don’t solve themselves—that, without American intervention, they metastasize.

At the moment, Syria, where history appears to be bending toward greater chaos, poses the most direct challenge to the president’s worldview.

George W. Bush was also a gambler, not a bluffer. He will be remembered harshly for the things he did in the Middle East. Barack Obama is gambling that he will be judged well for the things he didn’t do.

(End)