From Russia to Syria to Iraq to al Qaeda, President Obama and his aides have underestimated the motives and capabilities of U.S. adversaries.

With regard to some, the Obama team initially characterized bad actors as U.S. partners, such as in the cases of Russian President Vladimir Putin and Syrian President Bashar Assad.

In other instances, Mr. Obama ridiculed as a “JV team” the rampaging Islamic State terrorist group, said al Qaeda was “on the run” and declared Iraq secure as he pulled out all troops against the military’s advice.

“I think, unfortunately, that the Obama administration has put a higher priority on improving relations with U.S. adversaries — Russia, Iran and Syria before the Arab Spring protests broke out — than in advancing U.S. national interests and those of our allies,” said James Phillips, a foreign policy scholar at the Heritage Foundation. “As a result, many allies, such as Israel, Saudi Arabia, Egypt and Jordan have lost confidence in the administration’s leadership. The president’s admission that he has ‘no strategy’ for countering [the Islamic State] is not likely to instill confidence in his leadership.”

Michael O’Hanlon, a defense expert at the Brookings Institution, said Mr. Obama is rightly reluctant to get into another war.

“Arguably, with Russia, China and Iran, he’s shown a healthy respect for their capabilities,” Mr. O’Hanlon said. “In fact, part of why he doesn’t get easily into new wars is his view that they tend to be harder than first advertised.

“I’d say that even the intelligence community and other national security leaders probably underestimated [the Islamic State]. If they’d seen it coming, they might not have favored giving even limited support to the Syrian opposition, and might have preferred Assad as the lesser of two evils,” he said. “Alternatively, they might have fought harder against the removal of U.S. forces from Iraq.”

Of the Islamic State, Mr. O’Hanlon said “a lot of others got it wrong too. Few foresaw how rapidly [it] could metastasize, grow and expand militarily.”

Amid several crises, the president and his advisers have effected shortcomings in their analyses of overseas events and the world’s bad actors.

Russian President Vladimir Putin

In the 2012 presidential race, Republican Mitt Romney dubbed Moscow the No. 1 geopolitical foe of the U.S. because it protects despots such as Syria’s Mr. Assad and tries to disrupt American foreign policy.

At the October debate, Mr. Obama ridiculed the assessment: “Governor Romney, I’m glad that you recognize that al Qaeda is a threat, because a few months ago, when you were asked what’s the biggest geopolitical threat facing America, you said Russia, not al Qaeda. You said Russia. The 1980s, they’re now calling to ask for their foreign policy back because, you know, the Cold War’s been over for 20 years.”

In an earlier incident in which he was not aware a microphone was on, Mr. Obama was overheard in a cozy conversation with then-Russian President Dmitry Medvedev.

“On all these issues, but particularly missile defense this can be solved, but it’s important for him to give me space,” he told Mr. Medvedev, referring to Mr. Putin, then Russia’s prime minister.

Mr. Obama also began his first term by embracing a “reset” of Washington’s relationship with Moscow.

Whether Mr. Putin interpreted those statements and action as signs of weakness is unclear. But this year he ordered the invasion of sovereign Ukraine and annexed the Crimean Peninsula, ignoring Mr. Obama’s protests and threats of sanctions. He also has armed the Syrian regime.

Sen. John McCain told Fox News that Mr. Obama underestimated Mr. Putin’s desire to restore the Soviet empire.

“And so this president totally misread him, ridiculed Romney in their debate when Romney said that Russia was a major geopolitical foe,” the Arizona Republican said.

Iraq troop withdrawal

In December 2011, as the last American troops were leaving Iraq, Mr. Obama declared: “We’re leaving behind a sovereign, stable and self-reliant Iraq, with a representative government that was elected by its people.”

But the U.S. military had another view. U.S. Central Command wanted to keep 23,000 troops behind as advisers and trainers to cement the victory over al Qaeda and other Islamic insurgents.

And the Iraqis themselves expected a new status of forces agreement to achieve just that. Former officials say the White House made little effort to secure a new agreement that would have allowed U.S. counterterrorism forces to operate in the country.

Mr. Obama had campaigned on a promise to get American troops out of Iraq.

The Islamic State

After the U.S. exit, it took just weeks for foreign al Qaeda fighters to start pouring back into Iraq to attack the new government. Under Iraqi cleric leader Abu Bakr al-Baghdadi, the network of militants expanded in Syria and invaded Iraq as a terrorist army. It announced itself as the Islamic State of Iraq and Syria — now the Islamic State, and known by the initials ISIS and ISIL.

In January, as the al Qaeda offshoot began conquering territory in Syria and in western Iraq near the Syrian border, The New Yorker magazine asked the president about its threat.

“The analogy we use around here sometimes, and I think is accurate, is if a JV team puts on [Los Angeles] Lakers uniforms, that doesn’t make them Kobe Bryant,” Mr. Obama said. “I think there is a distinction between the capacity and reach of a [Osama] bin Laden and a network that is actively planning major terrorist plots against the homeland versus jihadists who are engaged in various local power struggles and disputes, often sectarian.”

In 2011 John O. Brennan, Mr. Obama’s then-chief adviser on counterterrorism, scoffed at the idea that an al Qaeda-type group could create an Islamic state, or caliphate, ruled by harsh Shariah law.

“Our strategy is shaped by a deeper understanding of al Qaeda’s goals, strategy and tactics,” said Mr. Brennan, now CIA director. “I’m not talking about al Qaeda’s grandiose vision of global domination through a violent Islamic caliphate. That vision is absurd.”

Today, the Islamic State has proclaimed a caliphate in wide portions of Iraq and Syria under its control.

On Fox News last month, Mr. Romney said: “The president has a foreign policy which has failed once again. He underestimated the extent of the threat represented by terror in the world, and specifically ISIS.”

Said Brookings’ Mr. O’Hanlon: “The JV comment was most unfortunate. I don’t think he’s under any such illusion now.”

Syrian President Bashar Assad

As the civil war in Syria began in March 2011 and Mr. Assad began a crackdown, the Obama administration portrayed him as a different kind of Middle East leader who would not resort to brutal tactics.

Then-Secretary of State Hillary Rodham Clinton said: “There’s a different leader in Syria now. Many of the members of Congress of both parties who have gone to Syria in recent months have said they believe he’s a reformer.”

At the same time, then-Sen. John F. Kerry, Mrs. Clinton’s successor at the State Department, said: “President Assad has been very generous with me in terms of the discussions we have had. So my judgment is that Syria will move. Syria will change as it embraces a legitimate relationship with the United States and the West and economic opportunity that comes with it and the participation that comes with it.”

The praise heaped on Mr. Assad was a major departure from the George W. Bush policy. The Bush administration considered Mr. Assad a bad actor for promoting terrorism and for allowing foreign al Qaeda fighters to funnel through Syria into Iraq to kill Americans.

Meanwhile, Mr. Assad has fought a brutal war for survival, resorting to using chemical weapons to kill hundreds of civilians. Mr. Kerry ended up calling him a “thug and a murderer,” but then complimented the regime for giving up its chemical weapons components.

Al Qaeda

During his 2012 re-election campaign, Mr. Obama repeatedly said al Qaeda is “on the run” and on a “path to defeat.” The network’s core operations in tribal areas in Pakistan were “decimated,” he said.

In February, Sen. James M. Inhofe, Oklahoma Republican, asked James R. Clapper, Mr. Obama’s top intelligence official, if al Qaeda is on the run or on a path to defeat.

“No, it is morphing and franchising itself not only here but [in] other areas of the world,” Mr. Clapper said.

“They are not [on the run],” added Lt. Gen. Michael Flynn, then-director of the Defense Intelligence Agency.

Mr. Obama has defended his national security policies. At one point, he blamed social media for making things look more chaotic than they actually are.

“Apparently, people have forgotten that America, as the most powerful country on earth, still does not control everything around the world,” Mr. Obama said at a press conference last month. “Our diplomatic efforts often take time. They often will see progress and then [take] a step backwards. That’s the nature of world affairs. It’s not neat, and it’s not smooth.”

Luke Coffey, a diplomatic analyst at the Heritage Foundation, said: “In just a few short months, the relations with Russia have gone from ‘reset’ to regret. ISIL has gone from ‘JV’ to ‘imminent threat.’ The administration has a habit of thinking it can bury its head in the sand and hope that the problems might take care of themselves.”

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