President Barack Obama’s expression of remorse on Thursday for the death of two hostages in a U.S. drone strike underscored one of the great frustrations of his presidency: His dream of extricating the U.S. from messy foreign conflicts remains just that.

Obama pledged in his 2013 inaugural address that “a decade of war is now ending,” but the numbers suggest otherwise. The U.S. takes regular lethal action in at least five countries. U.S. troops are deployed in three conflict zones. And America is directly involved in a pair of Arab civil wars.


Some administration officials fear that things will get worse before they get better, particularly in Ukraine and Iraq. But they are divided on how best to proceed, people familiar with the Obama team’s internal debates say — with top officials like Secretary of State John Kerry urging measures like arming Ukrainian government forces with Javelin anti-tank missiles, which can ostensibly be called defensive.

The goal, as one administration official put it, would be that “dead Russians will come back across the border and [Russian President Vladimir] Putin will feel a greater price for his escalation.”

But the roster of violence is sobering, and the president’s more cautious advisers fret about how much more military risk America should take on as global conflicts multiply.

In Ukraine, the administration is alarmed over fresh signs of another Russian military offensive that could shatter a February cease-fire agreement and turbocharge an internal debate about sending lethal weapons for Kiev.

In Yemen, Obama has lent logistical and intelligence support to a Saudi-led bombing campaign against Houthi rebels — despite concerns among senior advisers that the Saudi action is counterproductive and risks a confrontation with Iran.

In Iraq, as U.S. air strikes against the Islamic State in Iraq and the Levant continue, military planners are pushing for U.S. special forces to operate near the front lines when Baghdad’s troops mount a planned offensive against the ISIL stronghold of Mosul later this year.

Meanwhile, Obama’s admission Thursday that the U.S. accidentally killed two innocent captives near the Afghan-Pakistan border in January, including an American, was a reminder that the battle against Al Qaeda in that region remains unresolved even as new radical groups sprout across the Middle East and North Africa. In Afghanistan, Obama has been forced to slow the withdrawal of American troops and expanded their authority to conduct combat operations against the Taliban.

“We’re sort of seeing the world order cracking around the edges,” says Robert Kagan, a conservative author and historian whose writing has caught the president’s attention. “The only thing Obama can hope is that it doesn’t completely collapse while he’s still president.”

The administration’s allies challenge such assessments, saying there’s only so much America can do to directly influence the chaos now spanning three continents.

Brian Katulis, a senior fellow at the Center for American Progress close to Obama national security officials, said that the president has done an admirable job of managing the costs of the multiple global crises under his watch.

Obama “has maintained a cautious, ‘look before you leap’ approach, which I think is natural given all of the unforced errors by the previous administration,” Katulis said.

“No doubt, key parts of the Middle East are a mess and the tide of war hasn’t receded. But compared to where the United States was 10 years ago — bogged down in the middle of Iraq’s civil war with heavy U.S. troop presence straining our military and dividing our country — America’s overall strategic position is much better today than it was in 2005,” he said.

Still, Obama seemed to set a higher bar as recently as two years ago — suggesting that he could demilitarize America’s foreign presence more dramatically.

“America is at a crossroads,” Obama said in a May 2013 address at the National Defense University. “We must define the nature and scope of this struggle, or else it will define us.”

Obama was speaking specifically about the fight against terrorism before it cranked into a new gear with ISIL’s rise last year.

Some senior Obama officials worry about America’s mounting entanglements. Obama backed Saudi Arabia’s intervention in Yemen’s civil war only reluctantly. The decision followed a debate about whether it was better to oppose the Saudi bombing campaign against Yemen’s Houthi rebels, or to play a potentially moderating role, for instance by aiding target selection to reduce civilian casualties. Obama’s decision to send warships off Yemen’s coast also raised the prospect of a naval confrontation with Iran, which has been supplying the Houthis by sea.

In Ukraine, top officials are divided about whether to send lethal arms to forces battling Moscow-backed insurgents. So far Obama has sent only non-lethal aid, including body armor and night vision goggles, but Kerry and other advocates of providing weapons argue that the president’s caution has only hardened Putin’s resolve.

Much as he did in a 2012 debate over arming Syria’s rebels, Obama has so far vetoed more robust action. But on Wednesday the State Department warned that Russia is increasing its training and supply of the separatists in eastern Ukraine, including providing air defense systems and drones. More Russian troops are stationed on Ukraine’s border than at any time since October 2014, the State Department said.

“If there is an escalation” within Ukraine, “the debate will escalate within the administration” about lethal arms, said Ivo Daalder, Obama’s ambassador to NATO until 2013.

Until now, Obama officials have been mindful of German Chancellor Angela Merkel’s staunch opposition to lethal assistance for Ukraine. German officials say they expect that Putin would respond to efforts to arm the Ukrainians by further escalating the conflict, and Obama officials are sensitive to any appearance that they may differ with their European allies on the question.

For its part, Moscow is already accusing Washington of escalating the conflict. After a mere 300 American troops arrived in Kiev earlier this month on a mission to train Ukrainian forces, a Kremlin spokesman said their presence “could destabilize the situation.”

Iraq is another source of division. Military planners in particular believe that an Iraqi offensive to retake the country’s second-largest city of Mosul, now under ISIL’s control, can only succeed if it is supported by American special forces who can help to target air strikes. But even though Obama has sent 3,000 U.S. troops to the country in recent months, he is reluctant to place any of them near the front lines of combat.

Despite the tragic news of the January drone strike in Pakistan that killed American contractor Warren Weinstein and Italian Giovanni Lo Porto, the pace of operations in Afghanistan and Pakistan has slowed. The U.S. has only conducted five drone strikes in Pakistan this year, according to The Long War Journal, which tracks U.S. counterterrorism operations. And only one American has died in Afghanistan this year.

But the Afghan Taliban’s traditional spring offensive is just beginning, meaning that violence in Afghanistan — and America’s combat role there — will likely spike in coming months.

In March, Obama said that roughly 10,000 U.S. troops would remain in the country through this year — nearly twice the originally planned level. Last fall, Obama quietly granted the Pentagon the ability to support Afghan forces in battle against the Taliban after previously saying the U.S. would only conduct counterterrorism operations in the country.

That would seem to run against one of the most memorable lines from Obama’s 2013 speech: “We have to be mindful of James Madison’s warning that ‘No nation could preserve its freedom in the midst of continual warfare,’” he said.

But Derek Chollet, who left the Pentagon in February for the German Marshall Fund, said that a more instructive address is the one Obama gave upon accepting the 2009 Nobel Peace Prize.

“We will not eradicate violent conflict in our lifetimes,” Obama cautioned his dovish audience. “I face the world as it is, and cannot stand idle in the face of threats to the American people.”

Obama, Chollet said, has never been “under the illusion that we’re going to return to a peacetime state where problems are far away and we don’t have to be engaged abroad.” Instead, he said, Obama has tried to avoid “getting sucked into one particular theater” to the exclusion of others, to maintain a “strategic agility” around the world.

In practice, Kagan said, that too often means that Obama tries to influence the outcomes of conflicts while avoiding direct U.S. military engagement, largely by “subcontracting” security to countries like Saudi Arabia where possible. And he doubts Obama can succeed in multiple war zones by fighting “light.”

“It’s pretty clear we’re not going to do anything you can’t do from 30,000 feet,” Kagan said. “I just don’t think it’s going to work.”