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WASHINGTON — When Secretary of State John Kerry took the floor at the United Nations on Wednesday to deliver a searing denunciation of the airstrike on an aid convoy headed for the Syrian city of Aleppo President Obama was crosstown, at his Manhattan hotel, preparing for a day of diplomacy that included Africa, Israel and Colombia — but, conspicuously, not Syria.

It was typical of the arm’s-length approach the president has taken toward the Syria conflict on the world stage in recent weeks. At a summit meeting in China this month, he studiously avoided negotiating a cease-fire with President Vladimir V. Putin of Russia, leaving the diplomacy to Mr. Kerry and his Russian counterpart. At the United Nations, he scarcely mentioned Syria in a wide-ranging farewell address to the General Assembly.

Mr. Obama’s public distancing, White House officials insist, does not reflect a lack of concern. On the contrary, they say the president is desperate for Mr. Kerry to negotiate a viable agreement with Russia that would halt the relentless bombing of civilians in Aleppo and elsewhere in Syria — if only because he does not see a viable Plan B to stop the carnage.

But as Mr. Obama’s presidency enters its final months, the negotiations with Russia have become a threadbare exercise, leaving a president who has long avoided military entanglement with Syria backing a policy that he himself believes is destined to fail.

This week, his frustration boiled over publicly. The situation in Syria “haunts me constantly,” the president said in an interview with the historian Doris Kearns Goodwin, published Thursday in Vanity Fair.

In a mix of candor and defensiveness, Mr. Obama said he had second-guessed himself more on Syria than any other issue during his presidency. He repeated his rejection of critics who said he should have armed the moderate rebels much earlier in the conflict or carried through on his threat to take military action against the government of President Bashar al-Assad after he fired poison gas at civilians in 2013. But he conceded that there might have been a failure of imagination in his response to the conflict.

“I do ask myself, ‘Was there something that we hadn’t thought of?’” the president told Ms. Goodwin. “‘Was there some move that is beyond what was being presented to me that maybe a Churchill could have seen, or an Eisenhower might have figured out?’”

While Mr. Obama has supported Mr. Kerry’s diplomacy — even over the objections of the Pentagon — he does not want to be drawn into it. When Mr. Kerry met with Russia’s foreign minister, Sergey V. Lavrov, at a Group of 20 meeting in Hangzhou, China, on Sept. 4, the two fell just short of a cease-fire agreement over what officials said were minor details. American officials suspected the Russians were stalling so the deal could be sealed in a meeting the following day between Mr. Obama and Mr. Putin.

After 90 minutes, a stone-faced Mr. Obama emerged to say, “Given the gaps of trust that exist, that’s a tough negotiation, and we haven’t yet closed the gaps in a way where we think it would actually work.”

He instructed Mr. Kerry to keep talking to Mr. Lavrov, and the two came to terms five days later in Geneva. Mr. Obama, his aides said, was determined not to give Mr. Putin a platform to declare Russia was working hand in hand with the United States in Syria, particularly since he did not believe the Russians would abide by the terms of the agreement.

“The president wasn’t prepared to offer the Russians what they wanted most — a symbolic show of U.S. cooperation — until the Russians delivered on their end of the bargain,” said the White House press secretary, Josh Earnest. “That’s why the bargain is structured the way it is. And it’s rooted in our skepticism that they would deliver.”

“The president doesn’t want U.S. credibility to be sullied by Russia’s dishonesty and willingness to sacrifice principle in the name of convenience,” Mr. Earnest added.

Mr. Obama’s skepticism appeared warranted when the aid convoy was hit by a warplane that American officials believe was Russian. White House officials reacted harshly. Benjamin J. Rhodes, the deputy national security adviser, said, “The question is whether or not we just walk away from the table completely at this point, or whether or not we do some more diplomacy and consultation to determine whether or not there is some path forward.”

Again, though, Mr. Obama left it to Mr. Kerry to reproach Mr. Lavrov at a meeting of the United Nations Security Council.

To the extent he mentioned Syria during the General Assembly, it was in broad-brush humanitarian terms. At a meeting with other world leaders on the refugee crisis, Mr. Obama read a letter by a 6-year-old boy from Scarsdale, N.Y., who wrote to him to offer a home to Omran Daqneesh, the 5-year-old Syrian boy from Aleppo who was photographed, dazed and bloodied, after being rescued from an airstrike.

The White House recorded the boy reading the letter aloud, and the video went viral on social media.

Mr. Obama’s struggles with Syria are most palpable when he tries to sum up his foreign-policy legacy. In his speech to the General Assembly, for example, the president cited his diplomatic overtures to Cuba and Myanmar, as well as the Iran nuclear deal and the Paris climate accord, which he said exemplified the power of global collaboration. But when he referred to Syria, Mr. Obama spoke of constraints rather than possibilities.

“If we are honest, we understand that no external power is going to be able to force different religious communities or ethnic communities to coexist for long,” he said, referring to Syria’s sectarian rifts. “I do believe we have to be honest about the nature of these conflicts.”

Mr. Obama made no direct reference to the negotiations with the Russians, saying only, “In a place like Syria, where there’s no ultimate military victory to be won, we’re going to have to pursue the hard work of diplomacy that aims to stop the violence, and deliver aid to those in need.”

Several former administration officials said they understood why Mr. Obama was keeping his distance from the issue.

“Frankly, I doubt Obama engaging on the diplomatic side would help much,” said Robert S. Ford, a former American ambassador to Damascus who is now a senior fellow at the Middle East Institute. “Like Kerry, Obama wouldn’t have much leverage with the tough-nosed Putin unless Obama was also putting into play in the Syria war new elements of material — not verbal — pressure against the Assad-Russia-Iran alliance.”

Dennis B. Ross, a former coordinator of Middle East policy at the National Security Council, said Mr. Obama’s dilemma went back to the earliest days of his response to the Syria conflict, when he viewed it as a sectarian quagmire similar to that in neighboring Iraq. As the war ground on and the opposition became more Islamist, Mr. Obama’s options narrowed.

Now, Mr. Ross said, the president has little incentive to say anything. “He knows that anything he says either requires him to do something if it is tough — and he won’t — or makes him look weak and ineffective on an issue that will plague his legacy,” he said.

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