The outcome of Vladimir Putin's bold military gamble in Syria is far from clear, but in the short term, one loser seems certain: President Obama.
The Kremlin raised the stakes Wednesday by firing cruise missiles into Syria from warships nearly 1,000 miles away as Obama's critics at home and abroad said Putin's escalating attempt to bolster Syrian President Bashar Assad already has made the White House look weak and wavering.
The White House has been poised for weeks to quietly shift more U.S. military support to seasoned Kurdish militias and other rebel fighters in northern Syria. But at this point, any change in policy will appear to be in response to Putin's muscular moves, not a new initiative to help solve the multi-sided conflict.
Middle Eastern allies who have chafed at Washington's reluctance to plunge into the 4-year-old civil war have been impressed by how the Russian president has come to an ally's defense, even if they don't like his goals or his ally, Arab officials say.
In Washington, political leaders, from former Secretary of State Hillary Rodham Clinton, now the Democratic presidential front-runner, to Sen. John McCain (R-Ariz.), the 2008 GOP presidential candidate, are criticizing Obama for not doing more to stop a war that has killed more than 200,000 people, fueled Islamic State and sent hundreds of thousands of refugees fleeing to Europe.
U.S. officials also are furious that Putin's planes repeatedly bombed rebel forces armed by the CIA. Partly as a result, the administration has refused to give Russia's military the precise location of the U.S.-backed groups for fear it will paint a target on them.
Over the long term, Putin may end up stuck in a bloody quagmire in Syria, as the White House has warned, and Russia's first major military operation far from its borders since the Cold War may look like folly.
But for now, the result for Obama "is embarrassment," said Cliff Kupchan, chairman of the Eurasia Group risk assessment consulting group and a former State Department official. "Putin has him on the defensive."
A week after Russia surprised the White House by sending its warplanes to bomb rebels in western Syria, Putin shocked U.S. officials again Wednesday by launching 26 medium-range cruise missiles from four Russian warships in the Caspian Sea, sending them over American ally Iraq, and on to targets in Syria.
Putin took another shot at U.S. power Wednesday when he boasted that the first naval bombardment of the war "hit all the targets." He contrasted that with the errant U.S. airstrike Saturday on a Doctors Without Borders hospital in the Afghan city of Kunduz. Obama personally apologized to the group's leader, and the Afghan president, on Wednesday.
The separate and far larger U.S.-led coalition arrayed against Islamic State militants has launched more than 7,200 airstrikes in Iraq and Syria since August 2014, and only a few are known to have caused civilian casualties. The Kunduz bombing, which killed 22 people, was one of the worst such incidents by U.S. forces in 14 years of war in Afghanistan.
Russia has launched 112 airstrikes in the last week, and human rights groups have reported multiple civilian casualties, including three damaged medical facilities.
Russian warplanes also reportedly provided air support Wednesday for a ground offensive by Assad's forces, pushing north from the town of Hama.
Officials in Moscow hinted that Russian "volunteers" may soon join the fight, the same term they used for irregulars who backed pro-Russia separatists in Ukraine in 2014, sparking an international crisis.
From the White House's perspective, the problem is not only that Russia is propping up a leader who they insist must step down as a part of a political deal to end the bloodletting. It is also that Putin's moves seem aimed at emphasizing American hesitation and signaling a lack of respect for the former Cold War foe.
Over the weekend, Russia twice sent warplanes into the airspace of a NATO ally, Turkey. Although Moscow insisted that the cross-border intrusions resulted from bad weather and navigation errors, U.S. officials dismissed those claims and described them as deliberately provocative.
Russian fighters also have flown a "handful of miles" from U.S. reconnaissance drones in the region, risking a collision that could become a dangerous flashpoint between the countries, a defense official said Wednesday.
Putin and other Russian officials have scorned U.S. efforts to roll back Islamic State, the extremist group that controls vast parts of western Iraq and northern Syria. They particularly mocked a failed Pentagon program to train thousands of rebel fighters.
Over the last week, Moscow has seemed indifferent to the risk of a confrontation with Washington as Russian forces repeatedly attacked Syrian rebels armed by the CIA and allied spy services.
Russian airstrikes have hit Free Syrian Army units that were pushing south through the Ghab valley, an agricultural plain that rebels see as the gateway into Latakia province, a longtime bastion for Assad's Alawite minority in Syria.
The Free Syrian Army, parts of which received training and antitank missiles from the CIA, had coordinated a summer offensive with a group of Islamist militias that includes Al Nusra Front, an Al Qaeda affiliate. Both Al Nusra Front and Free Syrian Army forces were targeted in the first six days of Russia's airstrikes.
Only a few airstrikes targeted areas controlled by Islamic State, although Putin and other Russian officials insisted the extremist group is the principle target of their intervention.
U.S. intelligence officials believe that Russia is targeting militias that pose the most direct threat to the government of Assad.
It is an added benefit, from the Russian perspective, that some of those so-called moderate groups are U.S.-backed, said an American official who spoke on condition of anonymity to discuss internal assessments.
Bombing them helps bolster Assad and undermines Obama's strategy in Syria, two of the Kremlin's political goals, the official said.
Obama said at a news conference Friday that he won't engage in a proxy war with Russia in Syria, as America once did against the Soviets in Afghanistan, Angola and elsewhere.
Yet the administration is toughening its position on the Russian offensive.
Defense Secretary Ashton Carter on Wednesday ruled out any kind of strategic collaboration with Moscow. He said the two governments would seek only to ensure their aircraft don't collide.
"We are not prepared to cooperate in strategy which … is flawed, tragically flawed, on the Russians' part," Carter said in Rome. "What we will do is to continue basic technical discussions on professional safety procedures for our pilots flying over Syria; that's it."
The administration is clearly uncomfortable with how Putin's campaign has sharpened demands for more U.S. action.
Obama last week rebuffed Clinton's suggestion that the administration should set up a "no fly zone" and "humanitarian corridors" in the region to protect refugees.
But Secretary of State John F. Kerry and other officials are reconsidering those proposals in private meetings. Many analysts say Russia's presence has made creation of a protected zone even more difficult because of the risk of conflict with Russian aircraft.
Putin's gamble may accomplish several of his goals: increasing Russian influence in the Middle East and on the world stage, building his image at home, and shifting Western attention from his intervention in Ukraine.
But many analysts believe that neither Putin nor anyone else can wrest military victory from the bitter cauldron in Syria. And many expect Obama, who has made that argument since the conflict began in 2011, to continue to move cautiously.
Obama "has been pretty good about resisting pressure to get in deeper," said Kupchan. "I don't think he's going to react to Putin's gambit by upping the ante."
Times staff writers W.J. Hennigan in Rome and Carol J. Williams in Los Angeles contributed to this report.