During the 2008 presidential race, Gregory Craig—at the time a partner at the law firm Williams & Connolly—was one of Barack Obama’s strongest supporters, raising hundreds of thousands of dollars for the Democratic candidate, helping with debate prep and on the campaign trail. Never mind Craig’s longstanding ties to the Clintons—he was close with Hillary at Yale Law School, quarterbacked Bill’s impeachment defense as special counsel in the White House in 1998, and met Obama for the first time in 2003 at the home of the Clintons’ good friend Vernon Jordan.
Despite those loyalties, Craig was convinced years before the 2008 campaign began that Obama, not Hillary Clinton, was the right pick for the presidency.
It wasn’t surprising, then, that Craig landed President Obama’s first major legal appointment. After winning the election, Obama tapped him as his White House counsel—a job that put Craig in the middle of one of the President’s earliest fights: to do away with the interrogation techniques used under George W. Bush and to close the prison at Guantánamo Bay.
Craig had decades of political and legal experience. He had been a personal confidant and adviser to Senator Edward Kennedy on defense, national security, and foreign policy and had served in senior roles at the State Department under Secretary Madeleine Albright. He has spent most of his career as a litigator handling some of the nation’s highest-profile cases, such as the Elián González custody battle and, more recently, the defense of Goldman Sachs against an SEC probe.
After moving into the Obama White House, Craig churned out executive orders ending Bush-era interrogation policies. He also drafted the order that set a one-year deadline for shutting down Guantánamo. When Craig resigned as White House counsel in January 2010—a year after taking the job—the media ran with the narrative that he’d been pushed out over mismanagement of closing the prison, though the White House insisted that wasn’t the case.
Craig grew up one of four boys in Middlebury, Vermont. He went to Harvard before Yale Law. Craig is now a partner at the law firm Skadden, Arps, where he occupies a sprawling office on the 11th floor. A poster-size photo of him and Obama in the Oval Office hangs over his desk. Though the heady days of the 2008 race have given way to partisan fights over matters such as Guantánamo, health care, and the budget, Craig’s enthusiasm for the President doesn’t seem to have waned.
On a spring afternoon, he talked about his Washington career until his assistant entered, flashing a private note, and with that it was on to the next order of business.
You’ve said that when you first met Barack Obama you were convinced he had the ability to bring people together and end partisan bickering. Do you still feel that way?
I feel he has the capacity to do that and has made every effort. The fact that the polarization continues is not attributable to him. It’s attributable to the decisions the Republican leadership made during the first two years of Obama’s tenure, to oppose everything and anything that he supported. In fact, the Republican leadership made dramatic changes in their positions for the purpose of opposing him.
Let me give you an example, which would be Guantánamo. During the campaign, Senator John McCain supported closing it, as did Senator Lindsey Graham of South Carolina. They changed their position on Guantánamo so that suddenly there was a united Republican Party opposed to closing it that continues today. Everything Obama supports the Republicans have opposed almost as a knee-jerk reaction.
Would you have been an advocate of the one-year deadline for closing Guantámo if you knew all you do now?
The one-year deadline was necessary if this project was to be taken seriously. I guess if I had to change anything, I would love to have removed the problem of the economy going straight over the cliff as we came into office, because that was the preoccupying issue, and it edged out almost everything else. But if we didn’t have that year as a decision-forcing reality, we wouldn’t have made the progress we did make. And I believe that absent the opposition from the Republican leadership, we could have closed Guantánamo in that year.
When did you realize that wasn’t going to happen?
I guess it would’ve been late May 2009.
What was the turning point?
There wasn’t one turning point. When the President gave his speech at the National Archives in May, we still believed we had a chance to do it if we could get people to support our efforts to identify an alternative location [to house the Guantánamo detainees] in southern Illinois. But when it was clear that support for additional funds for that purpose was not going to be there—the Republicans were going to oppose it—it was clear that we were not going to make the year.
You knew this was going to be a complicated goal to achieve. What did you learn from that process?
I can’t identify anything specific. Perhaps we should’ve spent more time with the Republicans explaining the plan of action and trying to get them to agree to it, but from the earliest days I was briefing the Republican leadership in the House and the Senate and in the intelligence committees on both sides of Congress as to how we were proceeding, what the task forces were doing, and what our plan was. I’m not sure it was a failure of briefing on our side. I think they knew what we were planning to do, and they just disagreed.
What is it like advising somebody who is himself a great lawyer?
It was interesting because whenever we had meetings about a legal issue that we needed the President’s input on, it would fall to me to lay out the issue for the group. I would prepare the opening remarks so one side could make a presentation and the other side could make their presentation. This happened over and over, because we had meetings all the time where the President wanted to participate and always was interested in hearing the lawyers discuss various ways of doing something.
Invariably, we would be in the room—it could’ve been the Oval Office, it could’ve been the Roosevelt Room—waiting for the President to arrive. He’d come in, sit down, and lay out the case 20 times better than anybody else in the room could. We would already be a mile down the road after he finished his opening remarks. He did it brilliantly. I knew I was in the presence of a great lawyer whenever I worked with the President.
You took a larger policymaking role than is typical for a White House counsel. It puts you more in the middle of issues. Was that the right decision?
I am who I am, and the President knows who I am. Every White House counsel develops his comfort zone as to what he’s doing, what he wants to be doing, and that depends on his relationship with the President and the chief of staff.
The President is the client, the ultimate recipient of advice from his lawyer, and if the President doesn’t want his White House counsel to be involved in any of these policy discussions, he can make that clear. He never told me I was violating his expectations. To the contrary, he wanted me to be involved in policy issues and specifically invited me to get engaged in national-security issues.
You were at the forefront regarding the “torture memos.” You advocated for their release, amid skepticism from inside and outside the administration. Why was that the right call?
It was a decision to help the country understand how this had happened. Nothing new came out that the country did not already know, because President Bush had held a press conference and discussed the enhanced-interrogation techniques. He had talked about waterboarding. Bush’s attorney general and his director of the CIA had testified about waterboarding.
Around the same time that the Office of Legal Counsel memos were released, there was an article in the New York Review of Books based on the International Committee of the Red Cross interviews of detainees in Guantánamo, describing each of the techniques that were discussed in the OLC memos. There was nothing new in the OLC memos, so there were no secrets that had to be preserved.
In my judgment, the likelihood of a judge ordering those memos released was high anyway. It was the subject of a Freedom of Information Act lawsuit, and the real question was: Was President Obama and his administration going to be fighting tooth and nail against release of these OLC memos created by President Bush’s Justice Department, justifying the use of these interrogation techniques? Were we going to try to keep them out of the public domain or were we going to agree to release them? I think the President made the right decision. It was in the public interest, and it did no damage to national security.
The real concern—and the reason it was discussed at length inside and outside the White House with the Defense Department, with the intelligence community—was whether by releasing these OLC memos, the President could be seen as breaking faith with the people he had to work with in the future. Was this a betrayal of the intelligence community’s reliance upon these techniques’ remaining secret?
In fact, you saw the President going out of his way to meet with intelligence representatives to talk about this matter, and then to make clear that any person in the intelligence community whose activities were within the four corners of the advice they had gotten from the OLC with respect to the use of these enhanced-interrogation techniques would not be subject to any legal problems.