Transcript: Matt Olsen: The Line

Chuck Rosenberg: Matt Olsen, Welcome to The Oath.

Matt Olsen: Thanks, Chuck. It's great to be here with you.

Chuck Rosenberg: We're really glad that you could join us. You were born in Fargo, North Dakota. Is that right?

Matt Olsen: Yeah, born in Fargo, North Dakota. I moved as a young kid from North Dakota, to actually just about where I am now, not too far. I'm in suburban Maryland, just outside of DC and that's where I mainly grew up. But I did spend just about every summer in North Dakota as a kid were both my parents and my extended families are from western North Dakota,

Chuck Rosenberg: And what brought them to North Dakota to begin with?

Matt Olsen: My grandfather, Oswald Olsen, came from Norway, North Dakota, and Minnesota or many, many Norwegians in the early part of the 20th century, traveled and immigrated to North Dakota. My mom, she's mainly Lebanese, and it turns out there is a community of Syrian and Lebanese immigrants--around the same time, early part of the 20th century--who ended up in North Dakota. Then they met in a small town of Williston, North Dakota, near the Montana border.

Chuck Rosenberg: And do you have siblings as well?

Matt Olsen: I've got two younger sisters, both in California.

Chuck Rosenberg: Tell me a little bit about spending your summers in Fargo.

Matt Olsen: So because my dad worked for a member of congress from North Dakota, we would go back every summer he would go back for work to do the work of representing the state of North Dakota. And I would go back with him and usually the rest of my family. You know, I'd have the experience of being in sort of the prairie of western North Dakota, which is sort of the Badlands. And we're--my parent's families had been farmers--and that experience though, was that open land and freedom. So, what I remember mainly is free access to fireworks, miniature motorcycles, being able to run around and go wherever I wanted whenever I wanted--very different from my growing up in suburban Maryland, in Rockville, Maryland. Still pretty open, but a little more constrained experience growing up.

Chuck Rosenberg: You told us what your dad did for a living. How about your mom?

Matt Olsen: Yeah, my mom is a nurse registered nurse. I'm very proud of my mom for being one of the first people in her family to go to college, went on and became a registered nurse working in hospitals in Fargo and Grand Forks, North Dakota, in Minneapolis, teaching nursing, and then had a career in this area in nursing, including as a school nurse in high schools in Montgomery County.

Chuck Rosenberg: You know, neither of my parents went to college. But when I was in college, my mom finally went to college and became a registered nurse.

Matt Olsen: Wow, that's awesome. I didn't realize that.

Chuck Rosenberg: After college at the University of Virginia, you went to Harvard Law School. Why law school? Why Harvard?

Matt Olsen: I was thinking about going to law school like a lot of people in college studying political science and history. But my first job was at the Washington Post, as a copy aide and a news aide. I was thinking, at the time, of being a reporter. I grew up during Watergate. So, Bob Woodward, you know, a bit of a hero to me. And that was a model of how to really, you know, have a big impact on the world. So I worked at the Washington Post with the idea of like, yeah, I'd love to be a reporter. And I actually was talking to the reporters, and I talked to Bob Woodward at the time, and others. And what became clear was that you don't just apply for a job at 22 at the Washington Post, you go to the Des Moines Register, and maybe if you're lucky, the Miami Herald, you know, and you sort of move your way up. You know, I kind of wimped out I was like, wow, that seems like a hard road. I'm not sure I'm really willing to do that. I'll just apply to law school, and hope for the best. So, it was really that process that led me to go to law school. And then yeah, just fortunate to go to a really good one.

Chuck Rosenberg: Did you like law school?

Matt Olsen: First year, was disorienting, and strange and different from my experience a bit undergrad, you know, I got to study really interesting things when learning about torts and contracts and property, not so interesting. Second, third year, it felt very different and much more interesting. And I had a great group of friends. I ended up really loving law school to be honest, and having an overall great experience. I approached it probably a little bit more like a graduate school program than a vocational school program. And I think that made it really interesting.

Chuck Rosenberg: Were you convinced that you wanted to be a lawyer? Or was it a more linear or more obvious path than journalism?

Matt Olsen: I was convinced by my time in law school that I wanted to be a lawyer, I saw sort of the transformative power of being a lawyer if you approach it the right way, and take advantage of the opportunities that you have. And so, I was convinced that I wanted to be a lawyer. Now, I would say this is more with the benefit of hindsight, that there was a bit of a direct line between what I wanted to do right after college and working at the Washington Post and thinking about being a reporter, and ultimately what I did after leaving law school, working at the Justice Department, in particular, as a prosecutor, because of the similarities, really about learning about facts and presenting facts in a persuasive way and all the things that make up, as you know, being a prosecutor. There's a lot of similarities there between that experience and being a reporter, I think.

Chuck Rosenberg: Finding the truth.

Matt Olsen: Finding the truth, fundamentally finding the truth and presenting it. And that really is a similarity that's really fundamental.

Chuck Rosenberg: Well, you didn't go straight from Harvard Law School to the Justice Department, you clerked for a federal judge first, and I was hoping you would tell us about her because she's a remarkable lady.

Matt Olsen: Norma Holloway Johnson is who I clerked for. And you know, I was really just very fortunate, I applied to a number of different judges in the DC District Court. And I interviewed with Judge Johnson and she hired me as a law clerk and Judge Johnson, who has passed away, was the first black woman on the DC District Court, she had graduated among a very small number of women and one of the first black women to graduate from Georgetown Law School. She was a trailblazer at every step, she was a judge in the Superior Court, and then a judge on the federal bench at a time when there were very few black women, lawyers, much less judges, to be around her and just to learn from her and to see her lead and to be a judge was once in a lifetime experience for me.

Chuck Rosenberg: And speaking of leading, when she became the chief judge for the United States District Court for the District of Columbia, I believe she was the first black woman in the nation to be a chief judge on any federal district court.

Matt Olsen: That's right. Judge Johnson, when she was the chief judge, had a very challenging task in managing the investigation of President Clinton by Ken Starr, the special prosecutor.

Chuck Rosenberg: That might be a bit of a mystery to some of our listeners who are very smart, but may not appreciate that Ken Starr was an independent counsel, meaning independent from the Justice Department. But his work was actually overseen by statute by federal district court judges.

Matt Olsen: Right, it's a system that we don't have anymore. As you know, the Mueller investigation was under a different statute, but this was an independent counsel investigation, separate from the Justice Department of the President of the United States, the only oversight was through the chief judge of the US District Court for the District of Columbia, and in particular, the use of the grand jury to advance that investigation. So there were many issues that she had to deal with. And, you know, I would just say back about her, you know, what I saw many times, but I saw it in the context of that, as well as Chief Judge at the time, she would be in a room where she would be, again, often the only woman and almost always the only black woman. And here she was, you know, overseeing a roomful of men, white men, lawyers from law firms. And she was incredibly adept at maintaining order and commanding respect, and doing so with charm and kindness and grace.

Chuck Rosenberg: When you went to work for judge Johnson, was that the first time you took the oath?

Matt Olsen: Yes, that was the first time I took the oath in the judicial role of being a law clerk to Judge Johnson.

Chuck Rosenberg: Did she administer it?

Matt Olsen: She did. And it was in her chambers. You know, there's something special about that location, right? The chambers of a judge--as a lawyer, you know, as a young lawyer coming out of law school. It's a kind of magical place. It was, it was a moment I'll never forget.

Chuck Rosenberg: She passed away in September of 2011. Matt, Was she a good mentor,

Matt Olsen: She was a really good mentor. She was somebody who took an interest in her clerks. And Judge Johnson was not only like a brilliant jurist, she also knew the names of every cleaning person, every clerk, every reporter in the courthouse. She was a fixture in the courthouse, this was something that just stuck with me and you know, the cleaning person would bring her children in to meet Judge Johnson and Johnson talk to them about the importance of going to school, and being a good student, which was something that she felt really strongly about--is something that's always stuck with me, it's probably as much as anything else about her and the kind of legacy that she left, not only to the lawyers who appeared before, and our law clerks, but everyone who was around her.

Chuck Rosenberg: I'm so glad that you told us that about her. It was always so important to me to watch how people in positions of privilege and power treated people who weren't in positions of privilege and power. And we're all the same in the end, there's no difference. And the notion that you or I or Judge Johnson is any better than the man or woman who cleans her chambers is just I think, fraught with peril. We're all the same in the end.

Matt Olsen: Exactly.

Chuck Rosenberg: You eventually were hired in the Civil Rights Division at the United States Department of Justice as a brand-new trial attorney, just a few years out of law school in just a year or so out of your clerkship for Judge Johnson. Why civil rights, what attracted you to that type of work, Matt?

Matt Olsen: Really going back to law school, even college--I mean, this is one of those kind of crazy things. I took a voting rights class in college and learned about the Voting Rights Act. And it, you know, it just really stuck with me--the Voting Rights Act passed in 1965 basically changed the complexion of The South in terms of black voting registration.

Chuck Rosenberg: Probably one of the most important pieces of civil rights legislation in the history of the United States.

Matt Olsen: Absolutely, and it was a powerful, powerful law. It's still impactful today, although the recent cases in the Supreme Court have made it less impactful, but it made a, an impact on me as a student at the time, and it was something that I was always interested in, I wrote a thesis on it in college. But even going back to that early day of my sort of academic time, it was something that I thought, you know, I'd love to be in a position to work and enforce this legislation, because I saw what a difference it made. So, I was at a law firm, where I'd spent a couple years and I was looking to go into the Department of Justice. And I was particularly interested in looking in the Civil Rights Division. And so yeah, I was just fortunate to get an opportunity to go work on voting cases in the Civil Rights Division. You know, there's just a history to that of the Civil Rights Division, that goes back to the 60s and 70s, of lawyers having an opportunity to, on behalf of the United States, not defending the United States, but on behalf of the United States, change laws that are unjust, whether they're housing, or employment, or voting. And it go--and there are people who, you know, you know, made their careers in the Civil Rights Division, and I was really proud to be part of that, part of that for at least a couple years.

Chuck Rosenberg: Well, I wanted to illustrate that a bit. I know one of the things you worked on as a trial attorney in the Civil Rights Division was concerned the method of electing judges in Alabama to illustrate the work of the Civil Rights Division. What was that case about? What were you trying to accomplish? And what happened?

Matt Olsen: That particular case, the election of state judges, appellate judges in Alabama, one of the things that happened across The South after the Voting Rights Act was passed, was the adoption of a particular type of election called "At Large Election Systems." And there was plenty of evidence in many places, those were adopted for the purpose of diluting minority voting. So one solution to that is to draw districts that give effect to minority voters where they might otherwise be drowned out by an at large system, which is essentially a winner take all approach. There were many lawsuits brought across the south. And at that point, we were looking at the statewide election of judges in Alabama, which has effectively been on an at large basis. And as a consequence, black voters and white voters who tended to vote as a block with different candidates, because of the winner take all feature only those candidates supported by white voters were getting elected or universally. And so, we sued to change that, to draw districts, and to--and to ensure not the election of certain candidates and not to ensure the election of candidates of a certain race--but only to ensure that voters were able to have an impact in terms of their vote, and that their votes weren't drowned out by essentially blocked voting. And that was a strategy that was used by the Justice Department in many jurisdictions during that time period successfully.

Chuck Rosenberg: And that was what I was going to ask you. Was it successful? Did it work in Alabama? Did it work in other parts of the South? What was your experience?

Matt Olsen: It worked all throughout the South, it worked. I brought a case in Newport News Virginia, in fact, were similarly there was an at large election system. The city of Newport News city council was elected, you know, on this at large system, and there were about I can't remember exactly the percentage, but it was a significant percentage of the city was African American, like in the 30 or 40% range, but they weren't electing candidates of their choice. So we sued, we ultimately settled, the city agreed to draw districts and draw districts that actually gave effect to that group of voters. Um, so it was a very effective strategy. The Voting Rights Act, and the reason the Voting Rights Act was as powerful--one of the main reasons--is that unlike the Constitution, the 14th Amendment, which would require that the government or the plaintiffs in one of those cases demonstrate a discriminatory purpose, the Voting Rights Act only required a showing of a discriminatory result. So, it wasn't necessary to show that there was an intent to discriminate, only that the voting system had a discriminatory result. Those cases, they basically changed the electoral landscape in the South.

Chuck Rosenberg: By not having to prove intent, you had an easier burden.

Matt Olsen: Much easier burden by not having to prove intent, intent can be very hard. Now, that's not to say that in some cases, the government and plaintiffs, civil rights plaintiffs were able to prove intent because there would be a legislative record showing that these changes were adopted, particularly based on the timing, or sometimes even the statements of legislators. But again, with that, in many cases that would be difficult to show. So, the results test of the Voting Rights Act was what made it so effective.

Chuck Rosenberg: At some point, you leave the Civil Rights Division and become an assistant US Attorney in the District of Columbia. Why did you make that move, Matt?

Matt Olsen: Two reasons, Chuck, you know, one goes back to my time clerking. I remember clerking for Judge Johnson, there was a case, I did a lot of--a lot of criminal cases, I saw a lot of AUSAs coming into Judge Johnson's courtroom, I saw how you know, how effective they were, how good they were, often, I just thought that that would be a great, you know, role to play. And the other was a little more personal: my daughter was born, and my oldest and, you know, to be a lawyer in the Civil Rights Division means being on the road, it means being, you know, on the road, a lot, like if you're going to be, you know, really do the good, the best cases, you're gonna be spending, you know, two months in Tallapoosa County, Alabama, or, you know, wherever it may be. I didn't necessarily want to do that now that I had a job. So both those reasons together, but the first reason to be honest, was the primary one. I had seen the act, you know, I'd seen the AUSAs in action and thought that would be an awesome, awesome job.

Chuck Rosenberg: You did it for more than a decade.

Matt Olsen: Yeah, I did it for a long time. You know, the DC US Attorney's Office, we had a requirement that I think it was three, maybe four-year commitment, there was an expectation that you stay for a long period of time.

Chuck Rosenberg: And if I may, Matt, we should explain that the US Attorney's Office for the District of Columbia is both the largest US Attorney's Office in the nation, and is the only one in which the federal prosecutors Assistant US Attorneys, AUSAs, work both on the District of Columbia side and on the federal side, meaning you're both a city prosecutor and a federal prosecutor.

Matt Olsen: That's right, that makes that office unique in the federal system, by some measure, you know, in some accounts at the best experience, you know, for an AUSA, by others, it's you do spend a long period of time in your career in Superior Court, local court, before you get a chance to get to federal court. From my vantage point, it was an amazing experience. And you know, I spent the first--of my 10 years, my first really three or four, maybe even longer--only in Superior Court, effectively as a big city district attorney.

Chuck Rosenberg: Of the time you spent in the US Attorney's Office, you actually were detailed to the FBI for two of those years on the staff of Director Mueller. How did that come about?

Matt Olsen: Like a lot of things in life professionally, right, I happened to know a couple of key people. I knew Director Mueller's Chief of Staff Ken Wainstein, from actually having gone to college with Ken and worked with Ken in the US Attorney's Office. But I also knew director Mueller because, remarkably enough, Mueller had spent time in the US Attorney's Office in DC, really down the hall from me. And your listeners may well know this story because it's quite famous, at least in sort of the legal circles of Washington DC and Mueller-lore. But Mueller had been the Assistant Attorney General for the Criminal Division. He had been in the Boston US Attorney's office as first assistant, and US Attorney, I think, in Boston. But in any event, he had been at the highest ranks of the Justice Department. And then he left that, went into private practice, and as this--as I understand the story, was not so keen on private practice, and wanted to return to the frontlines and showed up one day in the DC US Attorney's Office, which as you point out, was a place where we prosecuted local crimes, and became a frontline homicide prosecutor, which really was just down the hall from me because I was also prosecuting homicide. So here you have this bit--sort of legend from the Justice Department, lugging his briefcase to Superior Court, you know, alongside me day by day. So that's how I got to know him.

Chuck Rosenberg: And one of the reasons he went to work for him when he became director of the FBI.

Matt Olsen: Exactly. So, when the opportunity came along to work for him. Yeah, that was, that was fortunate for me.

Chuck Rosenberg: Matt, I know you had a number of jobs in the Justice Department in the National Security Division in different roles. You've worked on the staff of the Attorney General, Eric Holder, I wanted to ask you in particular, about that. And one of the assignments that you had for Mr. Holder, where he asked you to lead an interagency effort to review the status of individuals detained at Guantanamo Bay. That has to be one of the most difficult jobs, one of the most taxing jobs, and I imagine, in some ways, one of the most frustrating jobs in all of government, but I would love for you to talk about that.

Matt Olsen: I love talking about the time I spent working on that Guantanamo Review Task Force. Really 10 years ago, now, it ended. It--yes, it was all the things you described, but it was also incredibly fulfilling and fun, you know, hugely challenging, but look, I'd been in the National Security Division. The Obama administration came in day one executive order to basically review these cases, review the detainees at Guantanamo.

Chuck Rosenberg: So, our listeners should understand the context for this: when Barack Obama became president, one of his priorities was to close Guantanamo Bay. In fact, he wanted to close within a year.

Matt Olsen: That's right. The Executive Order really called for Guantanamo Bay to be closed within a year, which was a campaign commitment, and one that, you know, became a day one priority for the President. Think back on that time, when I was in the Department of Justice as the senior career person in the National Security Division. So, during that period of time, I was the Acting Assistant Attorney General, which is the tradition, right, the senior career person stays on as the acting head until a new confirmed appointee was to come on board. And I remember at the time having been in the necessary division, being familiar with the Guantanamo detainees, thinking, this is going to be really hard. I'm not sure that the team coming in off the campaign fully appreciates the challenges of Guantanamo or other national security challenges. That's kind of the nature of transitions, right? It's the nature of when a new president comes in and new leadership comes in, they've been campaigning, and they've been making commitments, but then they kind of run into some of the realities of, okay, here are some national security imperatives and here's some of the challenges we face. But having said that, I was fully on board with the goal. I had seen the problems that we faced with Guantanamo firsthand from the Justice Department's point of view.

Chuck Rosenberg: What were the problems we face to Guantanamo?

Matt Olsen: You know, the initial idea of Guantanamo was sort of ill conceived, that there could be sort of a legal black hole where we could hold detainees--that had been, legally, a misguided proposition and had sort of failed. They were eventually given the right to challenge their detention in habeas proceedings in federal court in DC.

Chuck Rosenberg: What do you mean by "habeas?"

Matt Olsen: Yeah, habeas is a legal doctrine, that means basically, that you have the right to challenge your detention by a court and in the context of the Guantanamo detainees, as a result of a Supreme Court ruling, it was determined that they had the right to challenge the legality of their continued detention and bring a case in federal court in Washington, DC.

Chuck Rosenberg: And I presume many did so.

Matt Olsen: Almost every single one. And so, that was a significant amount of litigation, that the US was involved in defending those detentions. It created problems for us diplomatically. it was a real black mark for the United States that we had these detentions in Europe where we were seeking to, you know, elicit assistance in our counterterrorism efforts. It was a political issue, actually, that there was actual consensus around at least pre-President Obama, where both President Bush and Senator Obama, and generally others, including people like Senator McCain, supported closing Guantanamo. Now, that changed once President Obama came into office, the political support for closing it sort of fell apart. But the other challenge too, Chuck was the effort to try the detainees who could be tried in a military commission that had been set up that was largely struggling to get off the ground. And it's amazing to say that today, that that was true in 2010 and 2009, when President Obama came into office, and it remains true, which is a real travesty, to be honest.

Chuck Rosenberg: So, generally speaking, who was detained at Guantanamo Bay?

Matt Olsen: Generally speaking, so when I came into the role of leading the review, there were 240 detainees, they fell into several buckets, you know, some of them were serious, hardcore terrorists, Khalid Sheikh Mohammed, others who are were allegedly responsible for the 9/11 attacks. That was a small number, then there were others who were, you know, sort of Taliban officials who had been picked up and who met the requirements for detention under the laws of war. But the largest block were people with very difficult to discern pasts, some of whom had been low level trainees at camps in Afghanistan, who were picked up in the immediate days after the United States went into Afghanistan. And it was very difficult to determine: were these real, committed terrorists who were out to carry out attacks against United States or against the West, or in many, many cases, it appeared that they were people from a number of different countries, but particularly from Yemen, who had gone to support Jihadists in Afghanistan, but not because they were against the United States. It was a real mixed bag, but the biggest block were kind of what we would have called low level fighters, particularly from Yemen and Afghanistan.

Chuck Rosenberg: And what are your options, then? You mentioned that you had people ranging from hardcore terrorists like Khalid Sheikh Mohammed, the architect of the 9/11 attacks, to low level fighters who might not have had animus against the United States. So, what are the range of options open to you?

Matt Olsen: We had three categories. If we could transfer them to their home country or to a third country and feel confident that they didn't pose a security risk to the United States, that was one option. Another option was to prosecute them, either in a federal court or in a military commission. And we looked at those we could prosecute. And then, the third option, in some ways, the least desirable, because of the effort to close Guantanamo was to continue to hold these detainees under the laws of war, if they qualified, some were winning their cases in habeas, challenging whether they met the requirements for law of war detention. But as we basically broke them, though, this group of 240 into those three categories, the smallest category, if I'm remembering was about 40, or 45 of those 240 were approved for continued detention under the laws of war. And that was done with the unanimous agreement of a multi-agency, senior leadership group that was that sort of at the principal level, it was a very painstaking process that involved, you know, significant amount of effort by cabinet level officials, reviewing individual detainee files in the Situation Room over and over for hours and hours, because of how seriously I think President Obama wanted his cabinet to take these decisions.

Chuck Rosenberg: How does a cabinet level member--Secretary of State, Secretary of Defense, Attorney General of the United States--make a determination about risk? You said your first category was the one in which you resettle or repatriate transfer detainees back to their home country or to a third country willing to take them. But how do you make that risk assessment? What are the mechanics of that?

Matt Olsen: We would create, essentially, you know, reports, short reports to describe why this person was considered a risk, what their background was, and then also what the option was for transferring. So, if they could be transferred to a particular country, into a particular situation, where we had confidence and some, in some cases, assurances from that host country, that they would be monitored, for example, then, you know, you can make a judgment, you know, how much risk would that impose that the key is, and the challenge is, you can't eliminate the risk, you can never get to zero risk. And for a, an official, whether a member of Congress or an executive branch, to take a risk, to take any risk can feel hard. It's a difficult decision. And the President and Attorney General Holder really pushed this group to take on some risk to say, "Okay, this is a risk, but keeping Guantanamo open, keeping 240 people at Guantanamo, that's also a risk because of what's happening in terms our relationship with our allies." I thought there was a real ability of the leadership of the net security enterprise, basically the National Security Council to step up. The other person who helped lead that was john brennan, who at the time was Assistant to the President for Homeland Security and Counterterrorism. And he also really led the way to show that the administration was willing to take on some risk to close Guantanamo.

Chuck Rosenberg: John later became the director of the CIA.

Matt Olsen: Exactly.

Chuck Rosenberg: So, how many people fell into that first category where they were resettled or repatriated?

Matt Olsen: The decisions we were making were to transfer if we could do so while mitigating risk from a security perspective. So, for example, a number of detainees were approved to return to Saudi Arabia or Saudi Arabia, in some cases, would take individuals who were from Yemen, but had Saudi ties, and they would go into, at the time, Saudi Arabia ran a very effective rehabilitation program. So the State Department and Department of Defense would be part of the effort to move those individuals to Saudi Arabia. The hardest group of people that we started with, it's a fascinating story. And they were a group of Chinese Uyghurs who are picked up from Afghanistan had been training and camps and found themselves in Guantanamo. But were when I started this review, at the beginning of the Obama administration, had been ruled by a federal judge to not be lawfully held. They were not enemy combatants, they were not held lawfully under the laws of war, and they had to be returned, but there was no country to which the United States could return them.

Chuck Rosenberg: So, please explain for our listeners, who the Chinese Uyghurs are, my understanding is that they are an ethnic group of Chinese Muslims, and that we had some concerns about repatriating them to their home country.

Matt Olsen: That's exactly right. They are, they're Muslims, who lived in China. They are persecuted to this day significantly by China. At the time, in 2009, we--and this had been the policy the United States--we would not repatriate them because we were concerned about their humane treatment by the Chinese government. But at the same time, we were unable to identify another country, for example, a European country, that would accept the Uyghurs for resettlement. And so, there was--this was just a complete conundrum. There was no country that would take them, partly, I believe China was putting pressure on European countries not to take them.

Chuck Rosenberg: How many Uyghurs were at Guantanamo Bay?

Matt Olsen: I think, at the time I started this review is around 17 or 20, or so. So, a relatively small number. It was fascinating. Chuck, I went to Guantanamo early in this process and the Chinese Uyghurs were separated from all the rest of the detainees because they were not held lawfully. So, they were held in a barracks that looked like a regular army barrack, or basic, I guess, a Navy barrack. This is a Navy base, with the exception that they were surrounded by barbed wire. They were not held--in sort of catch 22 kind of language--they were not held, they were not detained because they couldn't be lawfully detained. But they also weren't free to move around the base because they didn't have that capacity either. So, they, they were on this barrack, but they were, you know, surrounded by barbed wire. It was absolutely bizarre. But it was a legal, political, moral conundrum for the United States to try to solve.

Chuck Rosenberg: And how did you solve it?

Matt Olsen: We solved it over time, but it was difficult. The first solution that we landed upon, was the decision to try to repatriate one or two Uyghur detainees into the United States, to resettle, I should say to the United States. Part of the logic there was if we were going to be able to resettle the rest in Europe, we needed to lead the way we needed to be a model. And, you know, it's kind of playground logic, if we're going to go to a European country and say, "Hey, we you accept some of these detainees, these weaker detainees or other detainees for resettlement?" we needed to show that we were willing to do so as well, you know, that would be the question. And so, we went and we identified the two least risky, we thought the lowest risk Uighur detainees, we interviewed them. And we then proposed these two for resettlement to United States. And as it turns out, there's a weaker community in Northern Virginia that was willing to work with resettlement and to help these individuals resettle in that community. Word of this effectively, there's this process was playing out, effectively leaked to a member of congress from Northern Virginia, who took to the floor of the House of Representatives and strongly worded statement opposed it and the political support for that quickly evaporated. And that no longer became a tenable approach. We had an agreement, though, to move them out of Guantanamo that we had, the United States had basically signed with these individuals and their lawyers as part of the resolution of their court case. So, to fulfill that commitment, folks scrambled in the government, in the US government, to find another solution, and they ultimately landed in transfer to Bermuda, in 2009, and those are a number of Uyghurs. I don't know if all of them, but a number of them, if I recall, were resettled it to Bermuda. And last I knew, they were still there.

Chuck Rosenberg: You described category one, those who could be resettled or repatriated with some risk, but minimal risk. But there are two other categories. As you described, category two were those who should be tried either in federal court in the United States or by military commission. Did that happen? And do you have a view on the proper venue?

Matt Olsen: So, we identified this group of individuals, detainees, who could be tried, whether in federal court or the military commission based on the amount what we thought was evidence that would be admissible in either one of those venues. And over time, actually, the military commissions looked more and more like regular federal courts with some important distinctions. But largely, you know, there were similarities in terms of the level of process and the way those systems operated. But the going in proposition I believed and sort of reflected in the executive order was to consider as a first option, US Federal Court, our federal courts, and we had a strong record of prosecuting terrorists safely and securely and justice with, you know, being met in the end. And one of the very first moves, in 2009, was to move one of the detainees who had previously been indicted in the Southern District of New York, for the 1998 East Africa bombings. And that individual was moved, early on in this process, to the Southern District of New York, and ultimately tried there. That became controversial, in part because it was done, you know, in the politics of Guantanamo and the way people reacted to bring a terrorist from Guantanamo into the United States. But Chuck, it also was controversial because he was, he was charged with, you know, a multiple count indictment, and he was ultimately convicted of one count and not convicted of the other counts. And while that one count was a conspiracy count that carried with it sufficient force to allow for a lengthy sentence, it only added to the controversy over moving detainees into the United States to try them in a federal court.

Chuck Rosenberg: You're talking about a detainees named Ghailani. And if I remember correctly, he was charged with 269 counts of murder, one for each of the victims in Kenya and Tanzania. And to your point, one count of conspiracy to commit murder was only convicted on the conspiracy count.

Matt Olsen: That result, again, in the context of the very fraught politics around Guantanamo, became problematic, and it became problematic for the real focus of the prosecution effort. And that was the 9/11 co-conspirators, including Khalid Sheikh Mohammad. That was one of the things I worked on the most in the course of, of the Guantanamo review was bringing together prosecutors from New York, from Washington DC, from the Eastern District of Virginia, your office, and, you know, I just put out a solicitation. When I started this process, I said you all I know that prosecutors in these offices have been looking at these detainees and trying to determine whether or not we could bring cases in federal court. And I know, I knew that these prosecutors had devised theories. So, I invited them to come to our office, we were set up in a secure office space where we had access to all the classified information, I said, these files rather for the first time, these individuals in some cases have been here 10 years or eight years, you for the first time, we're gonna have access to the information and make judgments about whether or not there's a prosecutable case in federal court. And so, that's the process that played out for a number of individuals, but most sort of acutely, for the 9/11 co-conspirators,

Chuck Rosenberg: Then there's a third category, the category of people who can't be tried, for whatever reason, but can't be released. How big is that group? And how do you think about it?

Matt Olsen: In some ways, that was the hardest group, because, you know, it was in a few dozen, that we that we decided that they couldn't be prosecuted, we didn't have evidence, remember, these individuals for the most part picked up on the battlefield? Right? There's not there's no Chain of Custody on documents, there's no, you know, statements are not admissible. There's, there could be very strong intelligence information from other sources, right, sources who would never testify. So, there was no way of bringing a case against them, even though the evidence was very strong.

Chuck Rosenberg: I'm really glad you made that point. There's a difference between information that you can use and information that you can't use, information that might be admissible in a court of law or in a commission setting, as opposed to information, let's say from a foreign government, that is an ally, that tells us something, and it's credible, but we can't use it in any public setting,

Matt Olsen: Just a fundamentally important distinction. And you know, it's one that people who don't really dig in on Guantanamo or similar issues might miss you know, so there's a view, there was a view from some that if you can't be prosecuted, you shouldn't be held, you know, you're not dangerous if you can't be prosecuted. And so, anyone who can't be prosecuted should be released. And that just turns out not to be true, because there were individuals about whom we had extremely reliable, extremely damaging information that came from right foreign government sources or our own sources or other sources that we could never present in a court of law. The you know, it's just a different set of standards. It doesn't mean it's not reliable. But it is something that you can never put up a cross examination in a public courtroom. And that was the challenge that we had with a number of these individuals who we were confident were very dangerous from a US national security perspective, but could not be prosecuted.

Chuck Rosenberg: But that's also unsettling in some ways. I mean, to your point, it is the hardest group, because you have to hold them, but you can't really explain why, at least not publicly.

Matt Olsen: That's exactly right. And that was, I think, coming in from the, again, early days of the Obama administration. I remember sitting and talking to people at the Justice Department who had been, you know, part of the new team coming in and having to try to explain, closing Guantanamo is not going to be just as simple as you know, prosecuting a few and letting the rest go. And, you know, I understand why if you're not inside the government, perhaps that might have been the impression because you don't have access to that information, right? And in a political problem, perhaps from for the new administration, who had made this commitment that that kind of ran headlong into the reality that there were individuals who were too dangerous. Now, I think to President Obama's credit I had, you know, I had the opportunity to try to explain this to him in I think it was April of 2009, in the Situation Room. I knew that it was not going to be welcome news, but he fully understood and appreciated that the risk of these individuals was very, very high.

Chuck Rosenberg: Like you. He's a Harvard Law School graduate, brilliant man, and good listener. What was it like to brief him on this very difficult issue?

Matt Olsen: At the second time, I had the chance to brief him and but this this was, this was really on me. And so, I was nervous, not only about just briefing the president of the United States, but about the fact that I was going to tell him something that I knew was going to be unwelcome. And I knew that right, I knew that I was going to say, "hey, look, we are not able to prosecute a fair number of these individuals." And I had a pretty specific number that we knew right then. It was difficult, but to your point, is obviously very smart, obviously, and also a very good listener. I remember him sitting there. And he, you know, he's left handed, and he was writing down as I was talking, giving him some numbers, and he was writing down those numbers. And he asked some questions about the nature of the information we had. It was certainly very well taken on board. There is no, there was no push back. Really, other than probing questions about the nature of the information, what we had done, and what we expected to find and what some of the options might be going forward.

Chuck Rosenberg: It's so important to be able to tell a president or any leader, for that matter, things that they don't like to hear, but need to hear. And you said you were nervous when you did it. I think anyone would be, but you were well received, nevertheless.

Matt Olsen

Yeah, 100 percent. And I knew that it had--that we had to do this as we had, you know, we had, and again, like, you know, you know this too, Chuck, from your, from all the briefings you've done, and mainly from being a trial lawyer, we mooted this out, you know, I had my team at the--on the GITMO taskforce, moot out the session that we were going into where someone played the president, and there's no substitute, right for trying to do that before you have one of these experiences. And so, we had done that. And so, it was all about being very well prepared and having, having the facts.

Chuck Rosenberg: So, what eventually happened, some number were resettled or repatriated, some number were tried, either in military commission, or in federal court in the United States. And some of those are ongoing.

Matt Olsen: Right.

Chuck Rosenberg: And some number remain held detained at Guantanamo Bay. What's the status right now, Matt?

Matt Olsen: You know, the numbers are really interesting in terms of the overall numbers of detainees at Guantanamo. I mean, there, there have been a total number of more than 750 detainees at Guantanamo overall.

Chuck Rosenberg: Although 240 when you took over the task force.

Matt Olsen: And 240 when I started this task. There are now about 40 detainees. I think the number might be exactly 40. That number reflects both, I think, a success and a failure. It's a success, right? That's a relatively small number at this stage. And so, a huge amount of effort by the State Department and the Defense Department to, over time, transfer out all but 40 detainees. But it's a failure in the sense that, you know, Guantanamo, almost 20 years in, remains a, you know, a place where these individuals are incarcerated when there are a number of other options that would allow the government to close Guantanamo. And it remains a problem in our history, I think, from a counterterrorism perspective. The idea of, of individuals going into their 50s and 60s and 70s, 80s at Guantanamo seems to me to be sort of morally unacceptable. We should be able to do a couple of things. One, we should be able to prosecute those who can be prosecuted in a federal court because the military commissions have effectively failed to be an effective mechanism of meeting out justice. And we should be able to, for those that cannot be released, we should be able to hold them in a secure facility inside the United States. But the idea of maintaining a, essentially, a federal prison on a naval base in, you know, in Guantanamo, it feels like a complete anachronism at this point.

Chuck Rosenberg: Are you hopeful? Or do you think we are stuck with men aging and dying as detainees in Guantanamo Bay?

Matt Olsen: You know, I'm hopeful, Chuck, I think this is not going to be a day one issue for any president at this point, right, like it was for President Obama, but there are procedures in place review boards and, and ways to continue to review these cases. So that over time, look, you know, these individuals, over time, do become less of a security risk. And I'm hopeful that at least with respect to the conspiracy case, or the case against the 9/11 conspirators that that case will be resolved, and we can move on. The biggest challenge, to be honest is the viability of the military commission. Whether it can ever be an effective forum for trying these cases, And that, to me, the lingering tragedy of a--one of them, at least--is that the case that had been teed up by Eric Holder when he was Attorney General, to bring that case to the United States to the Southern District of New York to try on an indictment that had been prepared, reviewed, and would be built on information evidence that would be presented on a federal court that that didn't happen. That case would have long ago been over and those individuals in my judgment would have been tried and convicted.

Chuck Rosenberg: I absolutely agree with you that my bias is to the federal court system of the United States. And you and I have both seen terrorism cases, prosecuted successfully, and repeatedly in the courts of the United States. And so, I share your dismay, I wish that case had been brought to the Southern District of New York a decade ago. And there's no doubt in my mind that it would have been resolved many years ago, and justly and properly and transparently.

Matt Olsen: Absolutely. And yeah, and so that's part of the real legacy that we continue to struggle to address. And, yeah, that will just who knows how that's gonna play out. But it doesn't appear that that case is going to go to trial anytime soon.

Chuck Rosenberg: And by that trial, you mean the 9/11 conspirators before a military commission at Guantanamo Bay?

Matt Olsen: Exactly.

Chuck Rosenberg: While a really important and difficult job, it wasn't your last job in government, I know you held a number of positions. But one of them I wanted to ask you about, I find utterly fascinating was, as the general counsel to the National Security Agency, NSA used to stand for "no such agency." It's become a little more public now, but not very much more. What can you say about it in an unclassified setting like this podcast?

Matt Olsen: Yeah, you know, I can talk about NSA quite a bit. And you're right, it's much more well known today than it was when I was there 10 years ago. But you know, the thing I would want listeners to know is, what a tremendous workforce is at NSA, the dedication of the workforce, the expertise of the workforce, the number of mathematician PhDs, the number of computer scientists, you know, it's an extraordinary valuable element of the intelligence community, and that what they do on behalf of the American people, often never known, right, but in protecting our national security, is really one of the crown jewels of the intelligence community of our national security enterprise. It, the other--what I saw, though, Chuck, from this sort of legal standpoint, was the attention that the workforce paid to protecting civil liberties and protecting privacy of Americans. That was sort of part of the kind of going in proposition for every operator, every engineer at NSA. The, the challenge that has to be said, is that, as much as that was part of the DNA of the place was to not interfere, not infringe on us civil liberties, 9/11 created challenges because all of a sudden, the adversary wasn't a Soviet official, you know, it clearly in a foreign land. The adversary had crossed over to inside the United States. And some of those lines that we had created to ensure that NSA's activities were outside the United States, and we're targeting non US citizens, some of those lines had become blurred in the counterterrorism fight, and that made their jobs very hard as they felt, "Okay, how do we take on this primary adversary, face Al-Qaeda, and not have another 9/11 happen, while still protecting the privacy and civil liberties of Americans? And that, you know, that the reality is, that's really hard. And if I could add one other element that complicated that, that effort, it's this thing called the internet. You know, it's one thing to know where two people are when they're talking on the phone, and to know that they're outside the United States on a landline. But, you know, when people are emailing each other, and those emails go through servers in California, all of a sudden, it becomes harder, again, to draw that foreign-US distinction. So, the legal issues are really hard--I mean, it was a fascinating job. And so, all the good intent of the NSA workforce, still, there are challenges in making sure that we always stayed on the right side of the line.

Chuck Rosenberg: Explain the difference between the NSA and the CIA.

Matt Olsen: It's really a division of responsibility of different types of intelligence collection. NSA is a signals intelligence agency. It collects signals, particularly communications, but other types of signals too. And it is the premier signals and agency in the world, bar none. The CIA is really known for collecting human intelligence, that's spies, human sources, collecting information to provide a decision advantage to US policymakers. The CIA also is an all source analytic function. So, there's a distinction between the collection of human intelligence, but when it comes to analyzing that information, all that information, for example, will go to the CIA to its analytic function where it's fused all different sources of information, it could be satellite imagery, it could be signals intelligence from NSA, it could be, you know, source information from CIA officers, but that's all put together analytically in an all source analytic product.

Chuck Rosenberg: You know, you and I both grew up in the Justice Department professionally, we both worked at the FBI--people who haven't had that privilege may not believe this. I hope they do. Because it's true, but they're very rule-oriented places. I mean, they are also staffed by human beings and human beings fail. And we read about their failures from time to time, but in the main, they're rule oriented places. And that was always my sense of the NSA, that it was a rule-oriented place, and that people took it very seriously.

Matt Olsen: Yeah, absolutely. I mean, I've worked at both the FBI and NSA, and they're similar in that regard, you know, give me the rule, tell me what the line is, I don't want to go anywhere near it, I want to stay on the right side. Problem is, at times, and particularly when there's been a crisis like 9/11, and technological changes, like the Internet, and the lines are harder to discern, in a way. You know, there's this famous, I think, just great analogy from Mike Hayden, talking about he wants his operators to have chalk marks on their cleats.

Chuck Rosenberg: Mike Hayden had been the director of the NSA, a four-star, Air Force General.

Matt Olsen: Exactly. He had been at NSA, he then went on to become the director at CIA. When I was at NSA, General Keith Alexander was the director, great, great leader. But Mike Hayden, he's from Western Pennsylvania, and loves sports analogies, and he talked about how, you know, having the operators should have chalk marks on their cleats, meaning, of course, that he wants them up against that line, you know, doing everything they can to protect the American people, which you totally understand, I totally get from the perspective of you're leading and intelligence organization, right? You don't want to leave anything undone to protect the American people. But as I've, you know, I've talked to him about this. And, you know, that's exactly right, I totally understand from his vantage point--from the vantage point of a lawyer and the general counsel, that's hard. Because if you want chalk marks on your cleats, that means you're going right up to that line. And hey, that line in the football setting is, you know, it's a white chalk mark, very clear, you know exactly where it is, it's straight as can be, it doesn't move. In the reality of the real world of, of intelligence operations, of collecting intelligence, it doesn't play out that way, right? The line is blurry, it's not straight, it moves, it's, it's as dynamic, you know, it's just, it's just not a straight, clear line. So, having chalk mark on your cleats means, you know, that you might have some real challenges. It's a fascinating debate, honestly, between lawyers and operators, like, what's the right approach? And it's a healthy one. And it's one I've had, right with people, with leaders like General Alexander that I've supported. How should we think about this challenge? And how should we think about where the line is, and what we should do? And that's an important conversation to constantly have, when you're conducting intelligence activities.

Chuck Rosenberg: The NSA has been uncomfortably for it in the spotlight, particularly with revelations generated by Edward Snowden, and the attention he got, or taking information that belonged to the NSA and to the United States government, and dumping it into the public domain. In what ways does that worry you?

Matt Olsen: What happened with Edward Snowden is concerning because of the information and the nature of the information that was released and the circumstances around it. I was gone from NSA when Snowden released that information publicly. I had worked on those programs while at NSA and also at the Department of Justice. One thing that I think is fundamentally important for folks to understand is that the vast majority of what was released by Snowden had nothing to do with privacy rights and civil liberties of US citizens. It had to do with the capabilities of NSA to collect information that it was lawfully entitled to collect around the world. People might disagree about those capabilities and whether the United States should use them in the way they're being used. And that's a healthy policy judgment that is ongoing, but what should not happen, in my view is for one person to decide that they don't agree with that policy, and to just put that information out into the public domain where those tools then become useless or at least compromised. And, and that's effectively what happened with the vast majority of the information that Snowden, Snowden released. I mean, it's a complicated issue in the sense that there, there, Snowden did have an impact on programs that had been lawfully authorized, but are now no longer lawfully authorized, that, in part because of the public attention that they drew, they were not reauthorized. And so, the argument could be made that because of Snowden, that's why those, those programs, which were that they went too far, and now the public knows about them, they shouldn't, they're no longer authorized. It's not one of those debates, I think, is easy to take one side or the other and just say that it's 100% right. What I think is clear, though, from my vantage point, is that for one person to just make that judgment on their own, to not bring that forward through venues and forms that were available to somebody, whistleblower type venues or members of Congress, for example, on the intelligence committees, and just to make that decision on their own is, I think, not defensible.

Chuck Rosenberg: I agree with you, Matt. I was at the FBI, I saw the damage, I really can't talk about it, but I agree. Some people believe, and I respect it, that he initiated a healthy debate. I don't believe that anyone who takes an oath to the Constitution of the United States has the right to take it upon himself or herself to make those decisions, and to dump in the public domain, highly classified information that operators around the world are using to keep us safe. We're far from perfect. And the debate has been healthy in some regards, but I share your view. Matt, your last job in government was also a very big, very important job: you ran the National Counterterrorism Center for three years, really a an organization responsible for all of our national and international counterterrorism efforts. In a way, a fusion center, a whole of government approach to analyzing information related to the national security of the United States.

Matt Olsen: Yeah, that was really the most, you know, incredible opportunity that I had as a, as a government employee, in a way was the lead the National Counterterrorism Center, as you said, a fusion center set up after 9/11, really out of the lessons of 9/11, fundamentally, that we, we had failed as a government to protect the country, in no small part because we didn't share information effectively. And we didn't take a whole government approach to counterterrorism. So, you know, at some basic level, the CIA had information, the FBI had information, the Defense Department had information, but there was no single hub, where that information was, was brought together, really crossing over again, that divide between the domestic and the foreign, that had been so ingrained into intelligence. Now, we had an attack from foreign elements, who had been able to infiltrate the United States, and we basically failed as a country as an intelligence and agent community and as the government to stop that attack. So, NCTC was built to address that shortcoming, and it's really been a high, you know, I think, a very successful agency over the course of its existence.

Chuck Rosenberg: How big is it?

Matt Olsen: It's about 1200 analysts, it's not big, by you know, US government standards. It's much bigger than any other country has of this nature. But it's, yeah, it's about 1200 analysts and operators.

Chuck Rosenberg: And the men and women who work for the National Counterterrorism Center come from different parts of the government, they're on loan, essentially.

Matt Olsen: Yeah, it's really one of the most important features of the workforce. And, and one of the animating principles was that this center should be staffed by individuals who come from other intelligence agencies who bring with them the expertise and experiences from the FBI and from NSA and from CIA, but also from the Department of Homeland Security and the State Department. And who then, in some cases, bring some of the authorities of those agencies with them to have access to certain types of information, and in the role that they're playing at NCTC, that information can be shared freely, so that we don't have that gap between domestic focused agencies and foreign focused agencies. That was such a problem on 9/11.

Chuck Rosenberg: One of the frustrations when you're in a job like that is that you can't talk about all the successes. But when you fail, we see it clearly. Has it succeeded, has done what it was designed to do?

Matt Olsen: I think it has definitely succeeded. It's succeeded in the sense that it has developed a model, the model that we've just talked about of a multi-agency staffed hub of information analytic expertise designed to make us much better at understanding the terrorist threat, analyzing it, finding those threats, and then operationalizing the response, leading the operational response. Because part of that role that I had, part of it, I reported directly to the Director of National Intelligence. And that in my case, that was Jim Clapper. But for the other part of my job, I reported into the White House and into the president. And that's the national security adviser, which was the operational arm of NCTC, which is to design plans and strategies for particular, counterterrorism challenges. And both of those were really important. And I think it's a model that is widely regarded as being successful. Now, we haven't stopped every attack, right, there are still attacks, whether overseas against the United States, and in some cases, inside the United States. So, by that measure, you know, there, there have been attacks that were not stopped.

Chuck Rosenberg: I'd love to hear just a little bit from you about your principles of leadership. You mentioned Judge Norma Holloway Johnson earlier, how she was not just brilliant, but also kind, and how she treated everyone with civility and respect. I happen to know you, Matt, so I know that you have always conducted yourself in that way too. But how do you lead an organization that big? And what principles did you follow?

Matt Olsen: I appreciate you saying that. I, like a lot of people who came up like you, Chuck, you know, trying cases, you learn to do things yourself, and you learn to be somewhat, sort of self-sufficient, you learn to take some risks. So, I--that was sort of the crucible that I learned how to be an effective lawyer. But as a leader, I would say, one of the models that I think about is my experience and playing basketball in high school. So, I happen to know, Chuck, that you are a very, very good basketball player.

Chuck Rosenberg: That was a very, very long time ago,

Matt Olsen

But at least, yeah, it's all relative, but I suspect you still are an excellent basketball player. I played in high school, and I was a point guard. And for whatever reason, you know, like a lot of things that in life, like, you know, you have these formative experiences, well, being a point guard is a particular role on a basketball team, where you are responsible for sort of leading the team, although not being the primary scoring opportunity, right, you're not looked to score as much as you are to help other people score by passing, by making sure that they're in the right place on the court. And so, that experience in some ways, I feel like it informed me as a leader. What I found as a, as a leader NCTC and in other roles, is that, you know, the people who are on the front lines, who are the scorers, you know, they're the ones who are doing the work, and who are taking those risks. And, you know, you're--my job as a leader is to make sure that they, that they have the support, guidance, the direction, the resources, you know, to be effective in those roles that we put them in. And so, for better or worse, I think that's the kind of leader I became--there's other models that are effective, but that was the model that it was sort of instilled in me at a impressionable age.

Chuck Rosenberg: I love the analogy. I also wish I had played with you because I'm--I like to shoot.

Matt Olsen: Yeah, you're a shooter. I've seen you on the basketball court.

Chuck Rosenberg: The work you've done on behalf of the United States government at the highest levels has been extraordinary. And I'm glad people get to hear from you because they are safer because of you.

Matt Olsen: I really appreciate that, Chuck. It's a total pleasure to chat about these issues with you. And we've done this a lot over the years, but thank you very much for giving me this opportunity.

Chuck Rosenberg: Well, thanks for joining us. It's an honor to have you here.