JUDY WOODRUFF: Looking at President Obama, he came into office with a desire to wind down America’s wars overseas and step up the focus at home, but events had a way of intervening, especially in the Middle East.

Tonight, we take stock of the president’s record in that volatile region.

Margaret Warner begins our look.

MARGARET WARNER: Shortly after taking office, President Obama traveled to Egypt to address the Islamic world.

PRESIDENT BARACK OBAMA: I have come here to Cairo to seek a new beginning between the United States and Muslims around the world, one based on mutual interest and mutual respect.

MARGARET WARNER: Yet, eight years later, the broader Middle East is a far more volatile place than it was.

Scholar Vali Nasr joined the administration to deal with Afghanistan and Pakistan. He’s now dean of the Johns Hopkins School of Advanced International Studies.

VALI NASR, Dean, Johns Hopkins School of Advanced International Studies: I think President Obama came to office with quite fundamental understandings in his mind about what’s possible and what’s not possible in the Middle East. The first, I would say, revolutionary breakthrough that he introduced is that the Middle East doesn’t matter to American geostrategy as much as we think.

MARGARET WARNER: That view colored the president’s approach to making good on two of his campaign promises: ending the U.S. war in Iraq, and investing more military resources to Afghanistan, where the Taliban was regaining ground.

In Afghanistan, the military reportedly wanted up to 80,000 more troops, on top of the tens of thousands already there, to mount an Iraq-like counterinsurgency campaign. The president ordered a review of the entire approach.

Michele Flournoy was the undersecretary for policy at the Defense Department.

MICHELE FLOURNOY, CEO, Center for a New American Security: There was a tug-of-war between people who had very ambitious, transformational goals in Afghanistan, and those who argued for what was sort of a good enough solution for Afghanistan and for achieving our limited objectives.

MARGARET WARNER: And did the president come to that, as it was known, Afghan good-enough objective?

MICHELE FLOURNOY: Yes, I think he did.

MARGARET WARNER: In December 2009, Mr. Obama announced 30,000 more U.S. troops for Afghanistan and pledged that, in 18 months, they would start coming home.

Nasr believes Afghanistan marked a pivot point for him.

VALI NASR: President Obama started by accepting the military’s counterinsurgency, but came out of Afghanistan having decided that counterinsurgency actually doesn’t work.

MARGARET WARNER: Instead, the U.S. turned to counterterrorism, relying more on drones and special forces to target terrorists.

In May 2011, that strategy produced a fateful raid on a compound in Abbottabad, Pakistan.

PRESIDENT BARACK OBAMA: The United States has conducted an operation that killed Osama bin Laden, the leader of al-Qaida.

MARGARET WARNER: To fulfill a second campaign promise, the president moved briskly to withdraw U.S. forces from Iraq, ending the U.S. combat mission in 2010. Negotiations to leave even a residual force foundered in a dispute with Iraqi Prime Minister Nouri al-Maliki.

MICHELE FLOURNOY: When we removed our forces, we lost our ability to reassure Maliki, to influence Maliki, and, absent that reassurance, he took a very hard turn towards sectarianism.

MARGARET WARNER: In early 2011, the Arab spring exploded. One of the first targets was a longtime U.S. ally, Egyptian President Hosni Mubarak. After failing to persuade Mubarak to plan his own exit, Mr. Obama spoke.

PRESIDENT BARACK OBAMA: An orderly transition must be meaningful, it must be peaceful, and it must begin now.

MARGARET WARNER: Derek Chollet was a top official in both the State and Defense Departments under President Obama.

DEREK CHOLLET, German Marshall Fund of the United States: The calculation was, if Mubarak’s going to go anyway, what position are we going to put ourselves in to be able to take advantage or have any influence in a post-Mubarak Egypt?

MARGARET WARNER: In Syria, peaceful protests in early 2011 against President Bashar al-Assad exploded into a full-blown civil war. In August, Mr. Obama said it was time for Assad to step aside. But he resisted giving mainstream rebels the weapons they needed.

Derek Chollet said the chaos that followed the limited U.S. intervention in Libya’s uprising affected the president’s approach to Syria.

DEREK CHOLLET: The initial questions were about, who was the Syrian opposition, how can we be sure that the capabilities we provide them don’t end up in the wrong hands?

MARGARET WARNER: That gave the upper hand to Assad’s forces and Islamist fighters. In 2012, asked what could prompt U.S. action in Syria, the president issued a now infamous warning.

PRESIDENT BARACK OBAMA: A red line for us is, we start seeing a whole bunch of chemical weapons moving around or being utilized.

MARGARET WARNER: One year later, Assad’s forces killed 1,400 people in a chemical weapons attack on a Damascus suburb. Plans were set for the U.S. and French to strike. But, suddenly, President Obama announced he would seek congressional approval first.

PRESIDENT BARACK OBAMA: While I believe I have the authority to carry out this military action without specific congressional authorization, I know that the country will be stronger if we take this course.

MARGARET WARNER: With no action by Congress, Secretary of State John Kerry, working with his Russian counterpart, Sergei Lavrov, pressured Assad to surrender the chemical weapons stockpile.

Michele Flournoy said the move shook U.S. credibility in the minds of some allies.

MICHELE FLOURNOY: I personally had allies from Asia on my doorstep the next day, asking what Syria and the red line meant for our guarantees to them.

MARGARET WARNER: This week, Kerry heatedly defended the choice.

JOHN KERRY, Secretary of State: Would it have been better to bomb them for two days and not get all the weapons out, and today those weapons would be in the hands of ISIL?

MARGARET WARNER: Kerry spent two years with Lavrov trying to get Assad and the rebels to a political settlement. Then, 16 months ago, Russia launched heavy airstrikes in Syria to shore up Assad. And last month, with up to half-a-million dead, and a refugee crisis swamping Europe, the U.S. was on the sidelines as Russia and Turkey negotiated a fragile cease-fire.

All this conflict also generated a new threat, the Islamic State. In 2013, remnants of the once-defeated al-Qaida in Iraq moved into ungoverned territory in Syria. They declared the Syrian city of Raqqa as their capital, then swept back into Iraq, capturing swathes of Sunni territory.

In January 2014, President Obama dismissed is as a J.V. basketball team. But after ISIS took Iraq’s second largest city, Mosul, and threatened Iraqi Kurdistan, the U.S. began airstrikes. The bombing campaign soon expanded into Syria.

PRESIDENT BARACK OBAMA: I can announce that America will lead a broad coalition to roll back this terrorist threat.

MARGARET WARNER: He would later add U.S. special forces, trainers and some troops in Iraq and Syria, where they remain today.

One goal President Obama fulfilled was to sideline Iran’s progress towards a nuclear weapon. Two years of negotiations among Iran, the U.S. and other world powers produced a deal in 2015. Mr. Obama struck the deal over strong objections from Israeli Prime Minister Benjamin Netanyahu, adding to tensions between the two over other issues.

Brookings institution scholar Shadi Hamid credits Mr. Obama for the Iran deal, but says:

SHADI HAMID, The Brookings Institution: I don’t remember ever hearing a real, live Arab say that Iran’s nuclear program was their number one concern or priority.

MARGARET WARNER: He also believes the apparent trade-off, making the U.S. reluctant to enter the fray in Syria, where Iran was helping Assad, wasn’t worth it.

SHADI HAMID: In the Middle East, we have learned everything is interconnected, and if we do one thing in one area, it can come at the cost of something else.

MARGARET WARNER: One week from today, dealing with that web of conflicts will fall to a new commander in chief.

For the “PBS NewsHour,” I’m Margaret Warner.

JUDY WOODRUFF: For more on this part of the president’s foreign policy legacy, we turn to three guests with deep experience managing national security policy and, in some cases, fighting the United States’ wars.

Retired General David Petraeus commanded American forces in Iraq, in Afghanistan, and for the entire Middle East. He also served as President Obama’s director of the CIA, a post he resigned in 2012. Ambassador Eric Edelman, he served in a variety of senior positions at the Departments of State and Defense, as well as the White House, and was a national security aide for Vice President Dick Cheney. And Philip Gordon, he served in the State Department under President Clinton and President Obama, and he served as the senior-most official responsible for the Middle East on Mr. Obama’s National Security Council staff from 2013 to 2015.

Gentlemen, we welcome all three of you to the program.

It’s a complicated region. There’s a lot to cover, but let’s focus on three countries.

General Petraeus, to you first.

Iraq, how do you size up the legacy of this president, President Obama, in Iraq?

GEN. DAVID PETRAEUS (RET.), Former Commander, Multi-National Force Iraq: I think it’s mixed.

Certainly, the developments of the last couple of years, when we have responded to the actions by the Islamic State, has gathered a considerable amount of momentum and actually taken back from the Islamic State all but one of the major cities, which is likely to fall in the weeks and months ahead.

But, prior to that, of course, there was a pulling out of our forces, various explanations for that and whether that would have, if we had been able to keep them, could have given us the influence to prevent the ruinous course that Prime Minister Nouri al-Maliki pursued that became highly sectarian and created the fertile fields for the planting of the seeds of extremism that the Islamic State exploited, before drifting into Syria and gaining lots of power in that civil war.

JUDY WOODRUFF: Ambassador Edelman, how do you see the president’s legacy in Iraq?

ERIC EDELMAN, Former State and Defense Department Official: I see it largely as a lost opportunity.

When General Petraeus and our mutual colleague Ambassador Ryan Crocker negotiated the agreement in 2008, I think all of us anticipated there would be a residual U.S. force staying after December 31, 2011. And I think we would have had more influence, we would have been better able to help prevent the rise of ISIS had we kept a residual force there.

JUDY WOODRUFF: And was that a mistake?

PHILIP GORDON, Former Assistant Secretary of State: Well, I think you have to remember the situation at the time.

On balance, would it have been nice to have a residual force? I think the answer is yes. It also happens to be the case that the Iraqis very much wanted us to leave. The Bush administration had agreed that we would leave by 2011, U.S. forces shall leave the country.

And so Obama was presented with a situation where you have the Iraqis asking us to leave, the U.S. public not wanting to say, the Iraqi parliament refusing to give the immunities we would need for our forces to stay.

So, while it would have been nice to have, you can’t pretend that the president, that President Obama could have just somehow come in and said, all right, we’re staying whether you like it or not. In that sense, one, it’s kind of a moot point whether it would have been nice, because it wasn’t possible.

But, two, I doubt, even though I would have rather seen some forces, that even a residual U.S. force, 5,000, 10,000, would have been enough to stop the very powerful trends that were going on in Iraq in terms of sectarianism, the rise of ISIS which was emerging from Syria, and all sorts of other things. So, yes, it would have been nice, but we should remember the context in which the president…

(CROSSTALK)

JUDY WOODRUFF: How do you see…

(CROSSTALK)

GEN. DAVID PETRAEUS: One of the paradoxes now is that we now have nearly 6,000 troops on the ground. And we do not have a parliament…

JUDY WOODRUFF: In Iraq.

GEN. DAVID PETRAEUS: We do not a parliamentary-agreed status of forces agreement.

Again, it’s just one of the ironies, the terrible ironies of a country that has suffered so much.

JUDY WOODRUFF: You want to button this up before we turn to another country?

ERIC EDELMAN: Well, General Petraeus made the point I was going to make.

I think we could have made a more serious effort with the Iraqis. I think they detected what Philip was talking about, which is that the president really didn’t have his heart in it and that the American people were tired of a long and difficult war.

JUDY WOODRUFF: Let’s turn to Afghanistan, Phil Gordon. How do you size up what the president — you were in the middle of all this. How do you size up what the president did, has done in Afghanistan?

PHILIP GORDON: On Iraq, General Petraeus said mixed. I think mixed would probably be our answer for a lot of these questions

And I think, in Afghanistan, that is probably the right assessment there as well. It can’t be better than mixed because Afghanistan is hugely dysfunctional. The Taliban are still there. I think, when the president decided early on to surge, he wanted to surge, he just wanted to deal with that threat and frankly get out and get out completely.

Well, the government is still dysfunctional and fractured, the Taliban is there, and we’re not able to get out completely. So, it’s not positive for all of those reasons, but it’s also not terrible, because we have achieved the minimal, which is keeping the government in Kabul in place and fending off, if you will, the Taliban.

JUDY WOODRUFF: General Petraeus.

GEN. DAVID PETRAEUS: And if you remember, the reason we went to Afghanistan and the reason we have stayed is to ensure that Afghanistan is not once again a sanctuary for al-Qaida or other transnational extremists, the way it was when the 9/11 attacks were planned there and the initial training of the attackers was conducted there.

We have accomplished that mission to date. Yes, we have had to keep forces on the ground somewhere in the neighborhood of 10,000 or so. That wasn’t the president’s plan. I think we should give him credit for backing off the plan of pulling them all out, which would have unhinged the country, and give some credit to the Afghans as well that they are very much shouldering the burden of fighting and in many cases dying for their country.

But it is a very challenged, troubled, difficult country, and has been throughout its history.

JUDY WOODRUFF: Ambassador Edelman, Afghanistan?

ERIC EDELMAN: I largely agree with what both Philip and General Petraeus have said.

I would say that I think the president’s decision to set a timeline at the outset of the surge in Afghanistan…

JUDY WOODRUFF: Publicly.

ERIC EDELMAN: Publicly — created difficulties that made it, I think, a harder row to hoe for General Petraeus and General Allen and others who succeeded them.

I — like General Petraeus, I give the president enormous credit for reversing himself and not insisting on a complete withdrawal during his time in office. But I do think the new administration is going to be facing a very tough situation.

And I agree with General Petraeus. We need to keep in mind that the reason we went there to begin with is not to allow it to be a kind of petri dish for Islamic extremism that seeks to attack the United States.

GEN. DAVID PETRAEUS: And my hope would be that there could be a sustained commitment at, again, a modest level that is a sustainable strategy in terms of…

(CROSSTALK)

JUDY WOODRUFF: You mean in the next administration?

GEN. DAVID PETRAEUS: Yes. Yes. Yes.

JUDY WOODRUFF: General Petraeus, you told us that Syria, the last place I want to ask you all about, is a place in which history is going to judge this administration most harshly. Why?

GEN. DAVID PETRAEUS: Well, I think what’s happened in Syria is that we have had rhetoric that has not, in the end, been backed up by resources and commitment, Bashar must go, a red line discussion of what a humanitarian catastrophe it was.

And, at the end of the day, we haven’t made the very, very difficult — and, again, there are no easy choices about Syria. I was at the table. There were never guarantees. But we didn’t take the very tough decisions that could have given us a chance in some of these cases, and where you’re pretty certain that if there wasn’t a decision or not sufficient resources, that it wasn’t going to succeed, in the way that we defined success at the time.

JUDY WOODRUFF: Phil Gordon, why was President Obama right not to retaliate, do something in a military nature after President Assad crossed that red line?

PHILIP GORDON: Well, I actually think he should have done something of a military nature after he crossed that red line. That was about chemical weapons. And he said, if they used chemical weapons, he would respond.

But I don’t think we should confuse that with the broader question of using military force to achieve our broader goals in Syria, like getting rid of the Assad regime. And there, if your question is why was he right, I think people should be very careful not to assume there was some modest use of military force that would have achieved the objective of getting rid of the regime and putting moderates in charge of a stable Syria.

In that sense, I think General Petraeus is right that there was a gap between the rhetoric, the ends and the means. But the critique that somehow, if only the president had given more arms to the opposition or set up a no-fly zone, that gap would have been closed, I disagree with.

JUDY WOODRUFF: Ambassador Edelman?

ERIC EDELMAN: Well, the administration’s argument for inaction in Syria was that doing some of the things that Philip just suggested would lead to greater violence, greater extremism, more radicalization, and in general a worse humanitarian situation in Syria.

However, there are consequences to inaction as well. And the inaction that we saw, I think, has led to a catastrophic situation, half-a-million people killed, 11 million people displaced, a migration crisis that is overwhelming the institutions of Europe, our closest allies.

And I do think — I agree with General Petraeus. I think, in retrospect, when people judge this administration historically, it will be seen as the biggest stain on this administration’s record.

PHILIP GORDON: I think that summary of the consequences of inaction is fair and accurate. No one who was involved with this policy would disagree that the consequences of the road traveled were poor.

But, again, we have to be careful not to assume that the alternative course of action, using military force, for example, would have had led to a better set of circumstances. It would be different circumstances.

GEN. DAVID PETRAEUS: I do think we have to be a little careful not to say that it was either this or either that, that it was either all-out military action to get rid of Bashar or it was nothing.

I do think there were alternatives, as have been discussed by the participants. Again, no guarantee that they would have succeeded, but it’s hard to imagine the situation could be worse than it is right now.

JUDY WOODRUFF: Well, we know we’re going to be debating all three of these places we have talked about just now and the rest of that part of the world for a long time to come.

For now, we thank all of you for being here, General David Petraeus, Ambassador Eric Edelman, Philip Gordon.

GEN. DAVID PETRAEUS: Pleasure.

PHILIP GORDON: Good to be here.

JUDY WOODRUFF: Thank you.