Does Obama Have Any Regrets About His Middle East Policy?

Once he’s made a decision, Barack Obama doesn’t seem like the kind of guy who lies awake at night worrying about whether or not he’s made the right call.

If anything, President Obama is the deliberator in chief. Before he decides, he carefully weighs the pros and cons, the yeses and nos of a policy issue, whether it’s health care or Syria. Indeed, I’ve heard from people who have worked for him that the president often argues both sides of an issue himself in his deliberation process.

Having observed Yom Kippur last week and done my own share of self-reflection and introspection, I started to wonder whether, nearly seven years into his presidency, Obama has any regrets, particularly in the one area of the world where matters have gone from bad to worse to horrible: the Middle East.

More often than, not smartest-guy-in-the-room types (and Obama is definitely one of those) don’t tend to look back much. Still, I suspect that at this point, with the Syria crisis deepening and Iraq in flames, with Libya disintegrated and Israel-Palestine as intractable as ever, Obama might have a few regrets. If I were him, these would be my top four.

The Syria red line

There are moments that become, for better or worse, unforgettable symbols of a presidency. Obama’s apparently unscripted answer in August 2012 to a question about reports that Syrian President Bashar al-Assad’s chemical weapons were not secure was one of those. Obama said: “A red line for us is we start seeing a whole bunch of chemical weapons moving around or being utilized. That would change my calculus. That would change my equation.”

There are probably few statements in his presidency that Obama wishes he could take back more than that one. Indeed, he must have wished so hard that more than a year later, Obama’s red line had strangely morphed into something else. “I didn’t set a red line,” Obama told a press conference in Stockholm in September 2013. “The world set a red line.”

The whole thing was a disaster from the beginning. The “red line” line was an off-the-cuff comment with no strategy behind it. It even surprised Obama’s advisors. The president was at best ambivalent about getting his country deeply involved in Syria, let alone conducting military operations. But then instead of walking back the comment, the White House figured it might show the president’s resolve and doubled down, at least rhetorically on their commitment to chemical weapons being a red line.

But in August 2013, when confronted with reports that the Assad regime had used sarin gas against the residents of Ghouta, resolve was the last thing the White House demonstrated. The president referred the issue of authorization for military action to a Congress that didn’t want to make a decision.

Some might argue that the U.S.-Russia agreement to remove Assad’s chemical weapons that emerged was more effective than a one-off military strike. But no matter, the president’s ambivalence and failure to enforce his own red line created an image of weakness that would became synonymous with the president’s risk-aversion on Syria. And it would become among the most famous lines of his presidency — a gift that kept on giving for his Republican opponents and a source of embarrassment for his administration and its supporters.

Syria, generally

A sentient, feeling man, and an internationalist to boot, Obama must be troubled by the catastrophe that is Syria’s civil war. Some 250,000 people are dead, many of them children; scores of thousands have been wounded, tortured, or kidnapped; and millions more have been traumatized and displaced both inside and outside the country.

Syria has become a moral, strategic, and humanitarian disaster for the Obama administration. The late Fouad Ajami predicted that it would become Obama’s Rwanda and the issue that he would most regret when it came to the shame of abdicating American power and responsibility. Others, including Hillary Clinton, have avoided that level of critical language but have focused on what Washington might have done differently. Only last week, David Petraeus offered a more expansive set of alternatives that are still possible, including establishing U.S.-protected enclaves where Syrian opposition groups can be trained and launching U.S. strikes against Assad’s air force.

To my knowledge, Obama has not expressed remorse or regret over not changing policy or doing more to end the violence. But he has done so on one Middle East issue: Libya. And what he has said about that country offers insight into why he hasn’t acted in Syria. In an interview with the New York Times‘ Thomas Friedman in August 2014, Obama showed why any regrets for not acting more aggressively in Syria have been tempered by lessons learned:

“I’ll give you an example of a lesson I had to learn that still has ramifications to this day,” said Obama. “And that is our participation in the coalition that overthrew Qaddafi in Libya. I absolutely believed that it was the right thing to do.… Had we not intervened, it’s likely that Libya would be Syria.… And so there would be more death, more disruption, more destruction. But what is also true is that I think we [and] our European partners underestimated the need to come in full force if you’re going to do this. Then it’s the day after Qaddafi is gone, when everybody is feeling good and everybody is holding up posters saying, ‘Thank you, America.’ At that moment, there has to be a much more aggressive effort to rebuild societies that didn’t have any civic traditions.… So that’s a lesson that I now apply every time I ask the question, ‘Should we intervene, militarily? Do we have an answer [for] the day after?'”

There you have it. In Obama’s view, Syria was Libya on steroids. And there were no good options. Military half-measures would lead to mission creep, and turning Syrian rebels into an effective force was, to use the president’s own words, a “fantasy.” Indeed, any intervention there would need to be massive and take into account the unknowns of the day after.

And there are other reasons Obama stayed out of the Syria conflict: He views himself as the extricator in chief, charged with getting his country out of unwinnable Middle Eastern wars — not getting involved in new ones that will require years of nation-building. Plus, the president knew that going all in against the Tehran-backed Assad regime wouldn’t help the White House achieve its other foreign-policy priorities, namely the Iran nuclear deal. And facts like the rise of the Islamic State and Russia’s increasing investment in propping up the regime in Damascus only make the possibility of intervention even more remote.

I have argued in this magazine that Syria is primarily not Obama’s fault or responsibility. But it’s unlikely that history will be as forgiving. The cruel reality is that as time passes, the complexities of the Syrian tragedy will fade and only one question will likely remain: Why didn’t the world, and particularly the world’s greatest power, do more to stop the killing?

The Iraq withdrawal

Given his long-standing opposition to the Iraq War and the pride with which he fulfilled his campaign promise and announced the withdrawal of U.S. forces in 2011, Obama probably doesn’t have any regrets about his decision to get U.S. combat troops out of Iraq. During much of his 2012 re-election campaign, that accomplishment figured prominently in his stump speeches: “Four years ago, I promised to end the war in Iraq,” Obama said in September 2012. “We did.”

Still, in the spring of 2014, as the Islamic State grew and expanded its reach in Syria and Iraq, there was a definite shift in the White House’s public line. The “we did the right thing” mantra continued, but the rationale for the decision took on another dimension. Asked in a news conference in June 2014 whether he had any regrets over not leaving a residual force in Iraq, the president replied:

Well, keep in mind that wasn’t a decision made by me; that was a decision made by the Iraqi government. We offered a modest residual force to help continue to train and advise Iraqi security forces. We had a core requirement which we require in any situation where we have U.S. troops overseas, and that is, is that they’re provided immunity since they’re being invited by the sovereign government there. So that if, for example, they end up acting in self-defense if they are attacked and find themselves in a tough situation, that they’re not somehow hauled before a foreign court.… The Iraqi government and Prime Minister Maliki declined to provide us that immunity.

This August, Obama echoed the same line, saying that the decision to withdraw was largely Iraq’s. Clearly as the situation in Iraq deteriorated, the administration became a bit more defensive about deciding to pull out U.S. combat troops. Full-blown regrets? Probably not. Listen to the president arguing against the view that leaving forces in Iraq would have made a significant difference. “So that entire analysis is bogus and is wrong,” said Obama. “But it gets frequently peddled around here by folks who oftentimes are trying to defend previous policies that they themselves made.” But even as Obama puts forward surety at press conferences, I suspect that in private there’s some second-guessing on whether the administration should have pushed harder for an accord that would have kept troops in Iraq.

The big overstatements on Yemen and the Islamic State

Finally, I’ll add two other ill-timed and poorly thought-out comments that I suspect the president wish had never come out of his mouth.

First, in the fall of 2014, Obama gave a statement on fighting the Islamic State: “This strategy of taking out terrorists who threaten us, while supporting partners on the front lines, is one that we have successfully pursued in Yemen and Somalia for years.” (The italics are mine.)

The president was no doubt correct in saying that U.S. strikes had eliminated some top al Qaeda in the Arabian Peninsula operatives and some members of al-Shabab in Somalia too. But it was always risky to consider the U.S. counterterrorism campaign in Yemen too narrowly and without context. It’s never smart to use the word “success” when you’re talking about a failed (or at least failing) state where local and regional actors can quickly complicate the big power’s agenda. Within months, the Houthis, former Yemeni President Ali Abdullah Saleh, Iran, and Saudi Arabia had turned success (in this region always a dangerous word) into a monumental mess. The collapse of any semblance of Yemeni central authority deprived the U.S. government of an ally in combating al Qaeda and opened up additional space for anti-American Islamists to operate. The counterterrorism campaign continued, with some success, but the president’s use of the word “successfully” as Yemen essentially collapsed made his argument look foolish and only fed the campaign of his adversaries.

Several months earlier, Obama had made a similar sort of mischaracterization. In January 2014, the president was interviewed by New Yorker editor David Remnick. And in the process, Obama gave a master class in why sports metaphors aren’t always appropriate. When Remnick asked about recent al Qaeda affiliates’ gains, the president said the following: “I think the analogy we use around here sometimes, and I think is accurate, is if a JV team puts on Lakers uniforms, that doesn’t make them Kobe Bryant. I think there is a distinction between the capacity and reach of a 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.”

Obama was correct in saying that these affiliates were more interested in consolidating their power in Syria and Iraq than in attacking the United States. But the interview was conducted several days after the Islamic State moved into Fallujah, and the group would continue on to advance in Syria and Iraq and to behead Americans and Europeans. The White House later went to great lengths to suggest that the president had been referring not to the Islamic State but to a range of smaller extremist groups. But this one just wasn’t going away, particularly as the Islamic State — far from being the JV team — emerged as unprecedented terrorist state.

Minus some doubts over Syria and likely a few statements he’d like to take back, I’d bet that this president is pretty satisfied with his Middle East performance overall. (He surely isn’t satisfied with the situation in the Middle East, though. How could anyone be?) But, he reasons, he played well with the bad cards he was dealt.

If Obama were going to have real regrets about the Middle East, he’d have to believe that he was responsible for the mess there (he doesn’t) and that there were other reasonable options (he doesn’t believe they existed). Instead, Obama believes that George W. Bush’s Iraq War created a good deal of the mess he now faces and that the Arabs themselves created the rest with the uprisings of 2011 that ended up being more a winter than a spring. Given his risk-aversion and the Middle East mess, he probably doesn’t think much about do-overs.

As Obama said at a news conference in July: “And ultimately, it’s not the job of the president of the United States to solve every problem in the Middle East. The people of the Middle East are going to have to solve some of these problems themselves.” History has no rewind buttons. And even if there were, I doubt this president would push them.

Image credit: SAUL LOEB/AFP/Getty Images