NEW YORK (AP) -- In a year of diplomatic breakthroughs, President Barack Obama can't escape the shadow of Syria's intractable crisis.
Obama arrived for his annual trip to the United Nations this week eager to tout the restoration of U.S. diplomatic ties with Cuba and the completion of a landmark nuclear accord with Iran. He shook hands with Iranian Foreign Minister Mohammed Javad Zarif, the first such encounter by an American president since the 1979 Islamic revolution, and held formal talks with Cuban President Raul Castro.
To the president, the openings with Cuba and Iran are not just validation of his own belief in the pursuit of diplomacy over military force, but also affirmation of a broader international order that marginalizes bad actors while giving them clear pathways to redemption.
The chaos in Syria, however, has defied all that. He returned to Washington Tuesday with the path forward no clearer than when he arrived in New York, even after lengthy talks with Russian President Vladimir Putin, Syria's most powerful backer.
"Nowhere is our commitment to international order more tested than in Syria," Obama acknowledged when he addressed the U.N. General Assembly.
After 4 1/2 years of civil war, the Syria war appears likely to be as much a part of Obama's foreign policy legacy as his diplomatic wins. The crisis has become the chief example for critics who say Obama's wariness of using military force has created a vacuum in the Middle East. His own administration still struggles to explain his 2013 decision to back away from airstrikes in retaliation for President Bashar Assad's chemical weapons use, an action by Assad he notably had said would cross a "red line."
To be sure, there's no guarantee that more aggressive U.S. action would have left Syria in a better place than it is now. White House officials often point to former President George W. Bush's invasion of Iraq as an example of the U.S. military overreaching in the region with deadly and costly consequences.
"We've seen -- at the risk of understating it -- the downsides of unilateral U.S. military commitment to conflicts in the Middle East," Obama spokesman Josh Earnest said Tuesday. "The United States and even the region is still paying the price."
Still, the situation in Syria only seems to be getting worse. What was already a gruesome civil war has grown into a humanitarian crisis and created yet another vacuum for terrorists to move in.
Diplomacy aimed at a political transition and Assad's removal has sputtered. Economic sanctions, a favorite tool of the Obama administration, have had little effect on the Syrian president. A plan to train "moderate" Syrians to fight the extremists now uncontrolled in the country has failed spectacularly.
Now Russia, a longtime ally of Assad, is entering the chaos.
Ahead of Putin's arrival in New York, the Russian president sent more military equipment and troops to Syria. He called on the leaders gathered at the U.N. to rally around Assad, portraying him as the only viable option for confronting the Islamic State.
Obama, in public remarks and private meetings, argued to Putin that supporting Assad was a losing proposition. He said the U.S. was willing to work with Russia on a political transition, but only if Assad leaving power was the result.
It's an argument Obama has made for years with little success. And to some analysts, it's unclear at this point what else he might be willing to do to persuade Putin to follow his plan.
"If he has leverage, it really would require him to show countries in the region that the U.S. will become more involved," said Anthony Cordesman, a foreign policy analyst at the Center for Strategic and International Studies.
White House officials insist that Obama's three days at the U.N. yielded some tangible signs of progress on Syria. They point to new commitments from Malaysia, Tunisia and Nigeria in the campaign to defeat the Islamic State, bringing the total number of countries to 65. The U.S. was also encouraged by France's decision this week to join the U.S. and Arab nations in launching airstrikes in Syria.
Even so, officials indicated they still expect to be straining for solutions to Syria's troubles when Obama makes his final appearance at the U.N. General Assembly next fall, just months before the end of his presidency.
"I would anticipate that a year from now, that we will continue to be having a conversation about what we can do to address the problems of Syria," Earnest said.