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.
Though so much about Bush’s interrogation and detainee policies was public by the time you took over in the White House, did anything surprise you?
The nature of the lawyering associated with the interrogation techniques. I don’t want to be overly critical of the lawyers who thought they were doing the job expected of them, but I thought they lost the forest for the trees when they tried to determine whether these techniques were cruel or inhuman punishment, whether it was torture by the definition of the laws against torture in this country or whether you used Eighth Amendment cruel-and-unusual-punishment standards. They clearly lost the big picture.
What did you learn about the dynamics of working in the White House? You worked under much different circumstances in the Clinton White House.
My job in the Clinton White House was much more focused. It dealt with one issue—the impeachment. Whenever that issue came up, I was in the room and knew exactly what was going on. What I found out, which is true in most human endeavors, not just the White House—it’s true in Congress as well as the military as well as in dealing with national catastrophes—is that the key to success is successful coordination. The White House is not a large institution, but for the White House to be successful, the various parts have to work together.
Why did you leave the Obama administration after a year?
I thought he had gotten from me what he wanted when he asked me to be White House counsel. He said, “I know you want to do national-security issues. I expect you to do that when you’re the White House counsel.” I thought I’d pretty much done as much as I could do for the President.
Your leaving didn’t have anything to do with Guantánamo?
I don’t think it had anything to do with Guantánamo.
Why did you decide to join Skadden rather than to return to your former firm, Williams & Connolly?
I was headed straight back to my old law firm when I got a call from an old friend, Cliff Sloan, and a wonderful new friend, Joe Flom. They urged me to take the time to try a different path. They asked me to set up a crisis-management team at Skadden and create a new practice group that focused on global issues and litigation strategies. I went to Skadden to explore new challenges and work on new projects that, using Skadden’s global platform, required international troubleshooting and problem-solving. It wasn’t that I was turning my back on my old practice; I was embracing a new one.
Talk about the strategy that went into getting Justice Sonia Sotomayor confirmed to the Supreme Court.
Early on, the President recognized that he was going to have the opportunity to make a Supreme Court appointment. He gave us the names of four or five candidates he thought we should start investigating and building files for him to look at—if they were judges, what their opinions were; if they were not judges, what articles they’d written, what speeches they’d delivered, what their background was. Everything from private issues having to do with health and family to public issues having to do with what they said on this issue or that.
The four or five names he gave us at the beginning were the four or five names we had at the end. As a teacher of constitutional law at the University of Chicago and as someone who was familiar with the judicial branch and potential nominees, he knew pretty much where he was going and who he was going to be considering.
Two things I would say were unusual: At the end of the day, it was his personal interviews of each of the finalists that resolved it. They were one-on-one, private interviews. I didn’t sit in on them. It was the President with his background information on the candidates, spending at least an hour with each, and out of that making the decision for Justice Sotomayor. The second thing we discovered was that the first 48 hours after the name is announced are critical for informing the public. They’re going to be interested, they’re going to draw their conclusions, and they’re going to get a first impression. During those 48 hours, the courtesy calls Justice Sotomayor performed, and then carried on during the month and a half that preceded the hearings, were absolutely critical.
What was the most rewarding part about your time in the White House? The most disappointing part?
Putting together the group that worked in the White House counsel’s office, having such an extraordinarily talented and dedicated group of people working for this President and being the head of that office, was to me the most satisfying thing I could do, and I was very proud of that.
I can’t tell you what the most disappointing thing was. Every day there are little disappointments in the White House. You have to learn how to live with those and keep going, and you can never let them throw you off your game.
How did you keep them from throwing you off?
If you’re a trial lawyer and you go to trial, you deal with stress. If you work in political campaigns, you deal with stress, and when you work in the White House, you deal with stress. It all has to do with expectations and performing at a high level, and that’s the life I’ve chosen.
What do you think the American people don’t understand about President Obama?
They’re finally discovering that Obama is a profound and old-fashioned patriot, that he is a deeply religious person, and that he works harder at his job than any President in my lifetime. People are only now appreciating how much he loves this country and how proud he is to serve.
You were close with Senator Ted Kennedy. Can you talk about the time you spent with him?
My relationship with Senator Kennedy changed over the years. I started out as a member of his senior staff. I was a foreign-policy adviser. When I left his office, I became much more of a personal adviser, lawyer, and counselor to him and to his family. During the later years, I was a very close friend, so there were phases in my relationship with him that were different. I think in the last 20 years of his life he was a magnificent legislator. And throughout his career as a senator, he set a new standard for what one individual in the Senate can achieve.
What personal impact did he have on you?
I have many memories about good times and tough times. In every memory, there’s a lesson. I will never forget how dedicated to his constituency in Massachusetts he was in every moment. We traveled all over the world, and we would go to Navy vessels. He would ask the captain to line up all the people from Massachusetts so he could meet every sailor and Marine that came from Massachusetts. Then when he got home, he would call their families, each and every one.
Going back to your time in the Clinton White House, that was clearly a remarkable moment in history. How did the President convince you to come on and coordinate his defense against impeachment?
He said, “I need you to help me do this.” And I said, “I’m not sure I can make much difference.” He persuaded me that I could and that he would be personally grateful if I would try.
It took a bit of work on his part, actually, because I was working in a terrific job for the Secretary of State and had been reluctant to get involved in the Monica Lewinsky matter. I had been watching from the State Department as August [1998] unrolled and he announced he was going to testify in front of the grand jury, and then he made a statement acknowledging a
relationship that was inappropriate with Ms. Lewinsky. About that time, the White House was calling and saying they needed someone to help coordinate an impeachment defense, and I did put them off a bit because I didn’t think I was the right person.
What was it like entering a White House that had already been dealing with this for months?
There were incredibly talented people in the White House. Many of them felt betrayed by what the President had done and angry that he had not been truthful with them. The First Lady was still very hurt and vanished from the scene for a couple months. When I went over there, I thought I would see more or as much of the First Lady as I would of the President, because I knew Hillary from law school—I knew her better than Bill Clinton.
I hardly saw her at all, maybe once, during the entire period. It’s not that she was absent without leave; she just wasn’t engaged the way I expected her to be. It’s hard to blame her. So yes, you’re right—the White House was besieged, beleaguered, and feeling deeply embattled.
You mentioned your relationship with Bill and Hillary Clinton from law school. When you decided to support then-senator Obama over Hillary, did you weigh any of that?
You don’t make these decisions lightly, but I did believe then and I believe today that Barack Obama was the right person for the country at that time, that his leadership on foreign policy—particularly on the war in Iraq—was leadership I could respect and follow. His personal life and his professional decisions were admirable, and his youth and stamina and love of this country—all of that persuaded me he was the right guy. I think the country grew to agree with me.
He did have the assistance of an economic catastrophe—that’s a bad way of putting it—but the economics were bad and so the incumbent party was in trouble. But he ran a magnificent campaign, and for him to have won the states he won is for the history books.
Are you still friends with Hillary?
I think so, yeah. We worked very closely when I was in the White House, and I think she’s doing a great job.
Circling back to impeachment, where were you and what was going through your head on the day of the vote?
It was December 19, 1998. It was a rainy day, cold and wet. The day began early because the Democratic caucus was meeting in one of the office buildings, to be addressed by the First Lady, who wanted to thank everybody for their support. It was a very moving, very emotional event.
I will never forget the details of that day. From the minute-to-minute debate on the floor of the House to the votes to the two articles of impeachment passed that day to the meetings that we had at the White House after the vote to talk about what next. It was a somber day.
What were you feeling?
That it was hugely important to our history what had happened, that it was a grotesque abuse of power in my judgment, that even if the President had done all the things they alleged he had done, it didn’t rise to the level of impeachment.
Did you emerge more cynical about the ways of Washington?
I was disappointed in the way the system operated. Unlike the impeachment process that resulted in a profile in courage with Andrew Johnson’s impeachment, I found that in President Clinton’s impeachment there were very few profiles in courage. There were 45 or 50 representatives in the House who had every reason to believe this was not an impeachable offense but did not have the courage to vote their convictions.
I believe that it was a naked abuse of power that was carried out by Tom DeLay and his staffers and that the history books should write that. This doesn’t make me cynical; it just makes me disappointed in the process.
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Marisa M. Kashino joined Washingtonian in 2009 and was a senior editor until 2022.
