Ambassador (ret.) Robert A. Sherman: President Obama's "Chief of Mission" in Portugal 2014-2017

Guest: Robert A. Sherman

Host: Donald R. Frederico

Recorded: May 17, 2022

Don: What compels someone who has had a successful career in the private sector to suddenly leave it for a completely different foray into public service, and more specifically into serving their country.

How does the child of immigrants raised in a small working-class city rise to become the representative of the President of the United States in an important European country?

And while we hear about ambassadors all the time, what do we really know about what it's like to be a United States ambassador in a constantly changing and uncertain world?

Robert Sherman - Boston lawyer, early volunteer for Barack Obama's first presidential campaign, and later appointee of President Obama to the post of U.S. Ambassador to Portugal - answers these questions and more in the latest episode of Higher Callings.

Bob: I think one of the things about the job is no matter what you think the job is going to be, it changes immediately. I thought I knew what my priorities were going to Portugal. And then a couple of weeks after I got there, Vladimir Putin invaded Crimea, and you have a situation with Portugal as a founding member of NATO, the issue is going to be what’s NATO’s response?

Don: I am with my friend and former colleague, the United States Ambassador to Portugal during the Obama administration, Robert Sherman. Bob, how are you today?

Bob: Don, it's a pleasure to be with you, my dear friend. And, please, I hope you will continue to refer to me by my first name. I spent three years being called nothing but Mr. Ambassador, Your Excellency, or Sir. It's nice to have my name back, particularly with old friends like you.

Don: Well, I appreciate that. And I think I already slipped and called you Bob, but you had already given me permission before we started recording, so I really do appreciate that.

So I want to talk with you today about the position you held as ambassador. You're now back in the private sector, but you spent a number of years in that role, a very important role for the State Department. And I want to cover those years. I want to begin though, by talking about your background, your previous commitment to public service, service to your country, and then how all of that led to your ambassadorship.

So how does that sound?

Bob: Sounds great.

Don: All right. Well, why don't we start with your personal background? I know a little bit about it. I know a little bit about your parents' history and I think that's important to cover, to lead into the conversation about your own personal commitment to public service and government service.

So why don't we start there? Tell me a little bit about your parents.

Bob: So, I think that it became very clear as I got older, that the values that I cherished as an adult were the values that were instilled in me by my parents as a child.

Both of my parents are Ukrainian. My father was born in Kyiv. My mother was born in Odessa. This was after the Russian Revolution. So they were Russian, and . . .

Don: Part of the Soviet Union? They were citizens of the Soviet Union?

Bob: They were. And back then, both my parents were from Jewish families and Jews were persecuted by the Soviets at the time.

My grandfather on my mother's side was a deserter from the Soviet army. He made his way across Europe, staying wherever he could till he came to the United States and was able to save up enough money to bring his wife, my grandmother, and my mother over. One of my mother's memories at age 10 is walking up the gangway at Ellis Island and her mother saying to her, "See that man standing over there? That's your father." For 10 years she never knew him.

My father's family, on the other hand, came over, my mother was 10, my father was eight at the time, came over. His parents contracted tuberculosis and both were sent to sanitariums to hopefully recover, which was far from a guarantee back then. And my father and his two brothers started life in this country in orphanages.

Fortunately, my grandparents did recover, probably miraculously, and then set about finding their children and reuniting the family. So that part of their lives really instilled in them an appreciation for what this country meant.

My father never went to college, but he did go to law school. He was working three jobs during the Depression when no one had jobs. And that impressed the Dean of BU Law School to give him a chance. He graduated law school, married my mother, opened up a law practice in Brockton, Massachusetts. He was a general practitioner. And then World War II broke out and he did what men of his age and generation did. He closed his office and volunteered to serve in the U.S. armed forces.

He served in the army in North Africa and Italy during the war, and my mother also took a job helping the war effort. I know that's not unlike your parents, Don. And as I said, that's what that greatest generation did back then.

Don: Yeah, really a remarkable ethic that our parents had. It was fairly common, but nonetheless, brave, courageous and faithful to the country. So that's wonderful.

I want to go back a little bit. You mentioned that your father went to law school without having gone to college. I guess that was possible back then. I think in most states that's not possible anymore, but it obviously shows a real dedication, intelligence, energy on his part that must've made him stand out among his peers who were interested in going to law school.

Bob: Well, I think part of it also came from his parents. Again, immigrants at the time were all interested in building a better life for themselves and their children. Same as today. And my father knew he wanted to do something more with his life than work as a waiter in a cafeteria or a switchboard operator, which he did overnights because it gave him a cot to sleep in and the housing he didn't have otherwise. So, this was something that he was intent on doing. And again, this notion of the promise of America, that you could come to this country with nothing but literally the clothes on your back and make a life for yourself and improve, was unique in the world.

And that's why people came here. And that's why people still come here.

Don: That's what we always have called the American Dream. I know we don't have time to get into this, but it's under attack in so many ways today. Things have changed so much since our parents' generation, but boy, we have them to look up to as role models. And I know you're grateful for that, and so am I.

Your father, I know, was quite an influence on you. How did his experience serving his country, serving his local community, and beginning a law practice, how did that influence your own thoughts about what you would do when you were of age?

Bob: Well, it's interesting because I grew up in a two-bedroom, one-bath house in Brockton. Extremely small. Which meant that there weren't very many places you could go where you didn't hear what else was going on in the house. And my father's rule was, at the time, that the office was open from nine to five, but work didn't stop at that point. He would come home for dinner, and then often at night he would meet with clients, and his office in our house was the kitchen table. So, my mother would put on a pot of coffee and my father would sit there with the client, and I could overhear, as these clients would tell my father about their problems, whatever that problem might be and listen to him as he gave advice in terms of how to solve the problem that they had.

And again, it could be by incorporating a business or it could be by defending a criminal case. It ran the gamut. But what I learned from that was that lawyers helped people. And that's what the job of a lawyer was, to take somebody who had a problem in life and help them through that problem.

And that was what was instilled in me and formed the reason why I wanted to go to law school. It wasn't to get a high paying job. It was to be in service, whether in service to people in the private sector or eventually, as I did, service to my state, country, in the public sector.

Don: Now you went to college in my hometown of Rochester, New York. We, we probably lived near each other for a few years and didn't know each other back then. Did you know when you went to college that you wanted to be a lawyer? Was that already your plan?

Bob: I did. I think again, it was probably unusual for people to really know firmly what they wanted to do. But again, I had my father as a role model for this. I thought it was pretty neat being able to solve problems.

Also the fact that I grew up in a relatively small community of Brockton. If he were trying a case, and I was done with school, I would go over to the courtroom. My mother would bring me to the courtroom and I'd watch him argue a case or a motion or something like that. So, to me, it was kind of pretty neat to see all this happening and that's something I wanted to do. So, yes, I did want to be a lawyer. However, the kind of lawyer I became changed during the course of my career and the course of my studies.

Don: Right. Right. And we're going to get to that. And you do have a very interesting background as a lawyer and ultimately ambassador. Well, you know, we kind of breezed through the fact that you and I both were in college when the Vietnam War was still going on. I know you, I think, went to a march in Washington . . .

Bob: I did.

Don: . . . to protest the war while you were in college.

But then after the war was over you went to law school. Did you know you wanted to go into litigation? Because you became a litigator after law school.

Bob: Yeah, I think the answer is yes. I liked the notion of the action. Again, it's a question of what the right fit was for me, and doing corporate law or tax law or something that was more sedentary, just didn't fit my view of what I wanted to do.

I also knew that one of the things I wanted to do as a lawyer was to somehow contribute to making life better for people. And litigation seemed to be the right vehicle to do that.

Don: At some point, you went to work at the Massachusetts Attorney General's Office, I think in the early 1990s. Can you tell us, how did that come about and what motivated you to make that move?

Bob: I think, like a lot of my career changes, it was being opportunistic and not being set in any one direction. During my career, I had taken on a lot of cases against the government on behalf of clients, whether they were individual clients, whether they were institutional clients, and the like that were, some in regulated industries by the government. I took on a series of cases for schools for autistic children, based on governmental action to deny services for those children.

So I had a pretty good understanding of the Attorney General's role in defending the government in those cases. And I felt at the time that the Attorney General, rather than being an independent lawyer for the agencies, were more beholden to the agencies. And I thought that wasn't the right way.

Don: In other words, you thought that they were viewing their role as counsel to the agencies, and less so counsel to the public.

Bob: Exactly. That the Attorney General is the chief law enforcement officer of the state. They make the decisions, and rather than acting independently to advise the agencies, they were just doing the agencies bidding reflexively.

So, in the 1990 Attorney General election, which was in the form of a primary, the current Attorney General, whose name was Jim Shannon, was being challenged by somebody named Scott Harshbarger. I thought, well, I have something to say about how that office works, but I didn't know the Harshbarger campaign at all.

One July day, I sat on my porch and I dictated a memo on reshaping the way the Attorney General's office conducted itself. Those were the days when you actually dictated something. It was before computers. And after the memo was completed, I got the fax number. Again, another anachronistic . . . .

Don: [Laughs] We still see them on people's, even on mine, I think I have my fax number on my email address, and I don't know whoever uses those anymore.

Bob: I don't know. I can't remember the last time I got a fax. But I got the fax number for the Harshbarger campaign. I had no idea who to send it to. So I just put "To Scott Harshbarger" and I faxed it in.

Sure enough, about a week later, I got a call from the Harshbarger campaign that said the candidate, who was the then-District Attorney in Middlesex County, was interested in meeting with me and would I be willing to meet? Sure. And I went over and I talked to Scott Harshbarger, who said he had the same view of the workings of the office that I did.

He ended up winning the primary, winning the general election. And, after that, he called me up and offered me a job in the Attorney General's office, which at the time was Chief of the Torts Division. That was a job that didn't interest me. It was defending the Commonwealth against tort claims. It was just not something that I was that interested in.

Don: It wasn't going to make you a lawyer for the people. Our current attorney general has been great at making it clear from the very beginning, the attorney general is the lawyer for the people.

Bob: Right. And I think that, you know, and again, a vehicle for change, a vehicle to do some good, and that wasn't it. And I politely told Scott at the time, thank you but no thank you. I wasn't interested. A little while later, I got another call from him, and he offered me the position of Chief of Consumer Protection. And, that to me was something where you could make a big difference. I had a large staff, I had a public role in the media. I had the ability to pick and choose cases I brought. In those days, the Attorney General's Office, the Consumer Protection Division, brought affirmative cases on behalf of agencies as well. And that's what I ended up doing for three years. And it was a fabulous job.

Don: I want to pause there for a minute.

It's a great story. And it combines two things. One is, obviously you had a vision for the office that was important in your getting that position. And it was important to Attorney General Harshbarger. But the other is you raised your hand, you know? And I had a very similar experience.

Mine was not in government. Mine was with the Boston Bar Association. But I saw a need within the bar association. I had been involved a little bit, not a lot. And I knew the incoming head of the Litigation Section of the BBA. And I reached out to him and said, "Look, I see this need and you should address it." And after a couple of weeks, he got back to me and said, "Yeah, we want you to lead it."

So it's very similar to your story. And I think it's really important because people need to understand, if they want to make a difference, one way to do that is to raise your hand. If you see a need, if you have a vision, let people know about it. Reach out to the people that are the decision-makers and let your views be known, and odds are they're going to come back, if they agree with you, and ask you to get involved in the change that you're trying to effect. So I think that's a great example of that, Bob .

Bob: And I think you're right. You know, my future boss, President Obama, used to say change comes from those who show up. And, that's the same thing that you're saying about raise your hand. That if you sit around and wait for things to come to you, you can wait a long time.

But if you want to make a difference, if you want to participate, you have to take that affirmative action. And then good things will come from that. It happened to you, Don. It happened to me as well.

Don: I'd like to get to your future boss. Now your past boss.

I remember when you got involved in that campaign. You got involved earlier than anybody I knew, at the very beginning of the Obama campaign. He was still somebody who was largely unknown. He was not favored to win the Democratic nomination in 2008. And I remember you were away in Iowa for long stretches of time. And I'd love to hear you talk a little bit about that experience and what it was that attracted you to the candidate.

Bob: Well, you know, it's interesting because, I think that, for those that are interested in getting into politics, too often what people try to do is handicap a winner. And I don't think you can do that. I think it's much more important to get involved in politics for somebody that you can, that you believe in, that you could get behind, than it is to try to think, okay, who's going to win. There are too many factors that go along with that.

But once again, I think fortuity smiled upon me. I had been involved in the Massachusetts governor's race before that, in the primary. Because of my background in the Attorney General's office, I had come to know the then-Attorney General who was running for governor, Tom Reilly. He had become a friend. I had helped him during his two terms as Attorney General. I became the vice chair of his finance team. The chair was a well-known political operative by the name of Alan Solomont at the time. And the bottom line was, that campaign was not successful.Reilly was the prohibitive favorite, again, another reason not to try to handicap campaigns. And this relatively unknown upstart by the name of Deval Patrick beat him in the primary and ran a better campaign, quite frankly.

So after that election happened, I had gotten to know Alan Solomont. I admired him. He was a long-time Democratic operative. He was very close to Bill Clinton. And he called me up one day and he said, "What are you doing about the 2008 election?" And this was in November of 2006. And I said "Nothing." And I knew where this was headed. I knew he was going to ask me if I was interested in supporting Hillary Clinton, which I was not, at the time. Not that I had much of anything against her, I didn't. I just think there was a lot of Clinton fatigue, that the country was in a different place.

And so, I said to Alan, "I assume that you're asking me whether I'd be involved because you're supporting Hillary Clinton." And he said, "No, actually I'm supporting Barack Obama." Which took me by surprise because I knew him to be a loyal guy. And I knew him to be a principled person. And I said to him "Why?" And he gave me a piece of political advice that I haven't forgotten. He said, "Because every election is about something, and this election is going to be about change. And even though I like Senator Clinton a lot, and I'm a big admirer of her, she's not the face of change. Barack Obama is."

And he said to me, he said, "Do you know Barack Obama?" "No," was my answer. I had seen him speak at the 2004 Democratic Convention, but other than that I didn't know him at all. And Alan said, " Would you be willing to take a call from him?" And my answer was "Sure."

A week later,

Don: And again, he was a senator at the time. He was fairly new to the Senate.

Bob: He was a newly elected senator at the time.

Don: And a relative unknown.

Bob: And a relative unknown, who, you know, most of the pundits and the conventional wisdom was, was not ready for prime time. And you know, he hadn't done his time in the Senate. He was there less than two years after being a state senator in Illinois.

Well, a week later, Senator Obama calls and he said, "I'm going to be in Boston. and I'd like to invite you and your wife to join me for lunch." And I said, "Sure." And it was just the four of us. It was Senator Obama, my wife Kim, me, and Alan Solomont, who had put this together.

And we ate lunch at the U. Mass. Club, and we talked about everything except politics. We talked about policy, how he saw the world. We talked about children and where they get their values from. We talked about the merits of the Red Sox versus the White Sox. But there was no political ask in any of this. And Kim and I walked away from that lunch saying to each other, that is the most impressive political leader we had ever met. Incredibly thoughtful and caring and kind and human, all of the elements that you're looking for.

Well, right after Thanksgiving - this was right before Thanksgiving - right after Thanksgiving, I got a call that said, "Senator Obama hasn't decided whether he wants to or run for President. He hasn't decided definitively whether he wants to run for President, but he's putting together a small group of people in Chicago in early January, that would form the bones of the campaign. Are you interested in coming?"

And I learned two things from that conversation. I later learned that Senator Obama had made up his mind about running. Michelle Obama hadn't made up her mind about their running. She still needed to be convinced.

And the second thing that I learned is that's the first test of loyalty. Are you willing to go to Chicago in January? It wasn't in West Palm Beach in January. It was Chicago, where it was bitterly cold. And I went.

There were 30 of us in the room at the time from all over the country. And the hierarchy of the campaign, David Plouffe, the campaign manager, David Axelrod, the chief strategist, Joel Benenson, the pollster, and Robert Gibbs, the communications director, were all there. And they laid out what a campaign would look like.

And there was no question about it. It was an insurgent campaign. The notion was, we have something to say, but the odds of our winning are not high. So that was clear at the beginning, but we were going to give it our best shot. The campaign was going to be a disciplined campaign, unlike other campaigns, the Kerry campaign in 2004, where the candidate was getting all sorts of differing advice from different people. This was structured more like a corporate organization, with Plouffe as the CEO, and then a row of senior vice presidents below. So there was discipline in it.

And there was also a phrase that was used from the beginning, which was "No drama with Obama." If you were in the campaign to kind of create something for yourself, you weren't needed. This was everybody focused on the same goal. So that's how I got involved. And I continued my work. Originally, we had to raise resources. So, I did fundraising. I did political work. You mentioned trudging through the snows of Iowa, which was . . .

Don: That's what I remember. I remember hearing about that. Because you were there, again, at the very beginning.

Bob: Yeah. It was a life-changing experience there. And again, we weren't expected to win Iowa. And the people that were there, it was a small group of us. And to this day, we are a band of brothers and sisters because of that shared experience in Iowa.

I did other political work for the campaign. I was also, by the way, in Pennsylvania and New Hampshire. And actually, New Hampshire, we had won Iowa in a surprise. We were way up in New Hampshire and the view was we were going to win New Hampshire and we were going to knock out Senator Clinton early and just cruise to victory.

But a funny thing happened. In a surprise, we lost New Hampshire. People were despondent. And Senator Obama walked into a small room of key supporters in New Hampshire, and he said, "This is the way it's meant to be. It wasn't meant to be easy. It was meant to be hard. We will be better off having lost this in the long run than if we had just won it and cruised to an easy victory."

And, you know, and it was amazing. I'm sure he was majorly disappointed at that time, but it was his sense of inevitability, a race is supposed to be hard and you'd have to earn it, that gave everybody a degree of confidence.

Don: That's really wise, you know. I've been reading and learning a lot about, and thinking a lot about how setbacks are actually often necessary to motivate, to learn from. You learn more from failure than you do success. So, very wise of him to not only perceive it that way, but also communicate it that way to his supporters.

Well, let's move ahead. I mean, you know, he obviously won the election, became President. You and I were practicing law together for a few more years. I ultimately left the law firm quite a while ago, but a very good law firm.

And then, after I was gone, I had learned that you had been nominated to be Ambassador to Portugal. How did that come about? And tell me what your thinking was about accepting that nomination.

Bob: Well, it actually starts four years earlier. It starts after the first election, the 2008 election against John McCain.

I had done, as I mentioned, a bunch of work. I had been in the war room on election night as part of a team to ensure that nothing goes wrong in a swing state with a voting machine, like Florida in 2000. I had done vetting for the national security positions in the administration. And, after the election, I was asked whether I was interested in serving.

It was a general question. It wasn't anything specific. And my answer was no. And the reason it was no was, first of all, I didn't get involved in the campaign to get a job. Secondly, I had been divorced and my children lived with me after my divorce. My youngest was still in college at the time. And so, this was not the time to be away from her. And third, I was newly married and my current wife who I mentioned earlier, Kim, ran a business in Boston. And so, she was well-rooted here. So it wasn't the right time in my life.

And I learned a bit of a lesson there too. And that is when you say no, they want you more. Because you don't have an agenda at the time. So I ended up taking on, in the first Obama term, special projects for the White House. At that point, my, my legal work was doing Foreign Corrupt Practices Act investigations and compliance. I was traveling around the world. I was down, I'd come back, I'd go down to the White House for meetings and for events.

Kim had been with me on that. It was a pretty heady time, you know, with the amount of time we were spending in the West Wing or just in the White House in general. And when the reelect came about, I reprised a number of my roles.

And right before the vote in 2012, Kim said to me, "You know, if he gets elected again, he's going to ask you if you want to serve again." And my answer to her was, "And I'm going to say no again," because again, I didn't do it to get a job. And at that point in my life, my marriage was the most important thing to me. And she was the one that said, "Not so fast."

She said, "I've been thinking about it. If they ask you to go to Washington, and what that means would be you leave Sunday night or early Monday morning, and you wouldn't come back till Friday night or Saturday," she said "You would have a separate life from me. And that's not something I'm interested in. But, if they were to ask you to go overseas and there's something, there's a role I could carve out for myself, then I think that if the setting were right, if the post were the right kind of post, that I could make this work, and this would be an opportunity for you and for us that may never come around and probably will never come around again. And we shouldn't overlook it."

So that's what happened. A week after the election, I got a call. This time it was to come down to the White House. The question asked was not, "are you generally interested," but it was more of a statement, "we'd like you to serve." I related word for word the conversation with Kim that I had just mentioned. They all knew her because of her involvement in the campaign.

And I said to them, "Well, if going overseas works, that's something that could work for us. If it doesn't, no problem. I'll just continue doing what I've done in the past." And they said, "No, that could work." And so that was what put me on the road to being a United States Ambassador.

Don: So, here we are. Let me recap a little bit. You are the son of immigrants in Brockton, Massachusetts. You go to BU Law School. You start working in a small law firm. You spend a few years in an important position in a state attorney general office. You continue working in private practice. You get involved in a presidential campaign.

Now, all of a sudden you're becoming a senior diplomat, the senior diplomat to Portugal. Tell me how you prepared yourself for such a new adventure and challenge.

Bob: There were a few ways that I prepared, but first and foremost, I can't emphasize enough the importance of my training as a lawyer. When you think about what a lawyer does, a lawyer is trained to analyze a problem, to listen to the opposing views that might exist, and to try to fashion a solution that works for his or her client. In my case, it's the same thing. The difference was my client was the President of the United States, but the skillset is exactly the same.

Don: What are some of the skills?

Bob: Well, I think the most important skill is listening. As an ambassador, you get a letter of instructions from the President of the United States, and the letter of instructions begins: "You are my personal representative in," in my case, Portugal. "You have the authority to make the decisions on my behalf within the country." And it also goes on to say what your title is, and it's not “Ambassador.” It's “Chief of Mission.” That the mission of the United States government in a particular country and the people there regardless of agency report to the ambassador. So, I think that when you think about what the job really entails, it is really three-fold, and the skills that are required fit into this.

I used to say I have three jobs. Number one, I was the personal representative of the President of United States. So, as you say, the senior diplomat in the country. I was empowered to represent the interests of the United States within the government of Portugal. And that became very important, particularly since Portugal is a founding member of NATO and Strikeforce NATO, the naval command and control part of NATO, is located in Lisbon.

But I was also the CEO of an organization. That organization happens to be the embassy made up of all sorts of divisions. We had political people, economic people, public diplomacy people, communications people, all working for the State Department. They reported to me. We had commercial people whose job was to advance the commercial relationship between U.S. businesses and Portuguese businesses. They were employed by the Department of Commerce. They reported to me.

We had the intelligence agencies, more than one, all with three letters. They reported to me. We had military people, again, under the letter of instructions, military personnel not under the command of a combatant commander, like the commander for Iraq or Afghanistan at the time, that were in the country, reported to the ambassador. Law enforcement people, FBI, DEA, Homeland Security, Secret Service, among others, all reported to me. So as the CEO of this organization, you have to bring people together for a common mission.

And then the third thing that I was, was I was the mayor of a small town. There were births, there were deaths, there were divorces, there were all sorts of issues. And sometimes I was the cheerleader-in-chief, sometimes I was the mourner-in-chief, but within the embassy community, and that extends to the Portuguese members, the American members, their families, and the like, I was the visible presence at that time.

So, bringing into that was not only the diplomatic skills of listening and problem solving. It was the skills of empathy when somebody was going through a problem. It was the skills of organizational management to be the CEO of that operation. So, there's quite an array of skills to be brought to bear in the job that you have as ambassador, chief diplomat, and chief of mission.

Don: So it was really not only your legal training, but even more so, your experience as a lawyer that helped you develop those skills and then bring them to bear in the very important position of ambassador.

Bob: Yes.

Don: I remember hearing you tell a story about one of your first experiences with the military, and it involved a salute. Can you tell that one? I'd love for our listeners to hear that.

Bob: Well, I think the thing that is also a heady experience is that as an ambassador in a country, you are the highest ranking official in that country. The only difference is when the Secretary of State or the President is in that country.And that was brought home to me in spades.

Now, in preparing to be an ambassador, you do a lot of training. They don't just send you on your way. You spend a lot of time in Washington learning about the functioning of an embassy, how to run an embassy, but you're also learning the substance of the job that you have.

What are the issues, not only in the country, but what are the multilateral issues? The NATO issues? The EU issues, in my case, and the like? And the other thing you have to learn are the security issues. If the embassy is under attack, how do you call in the Navy SEALs? You know, you don't just dial 411 and ask for the Navy SEALs.

So, the arrangements were made for a group of us to fly down to MacDill Air Force Base in Tampa, where U.S. Special Operations Command is located, and to spend a day with the special operators learning about what they do and learning about how you call them in if it's needed. And I'll tell you, the special operators are as much marketers as they are door kickers and trigger pullers.

We flew out of Andrews Air Force Base on a special operations plane, which they had parked next to Air Force One. So you get off the little mini bus that takes you to Andrews. You walk past Air Force One, get on the plane. The first-class cabin is in fact a mobile operating theater. So, if the special operators are in what's known as a wet zone, in other words, there's blood, and they need to be attended to, the first-class cabin converts into that. And we rode down, landed at MacDill, and there were about eight of us. And some of us were rookies, some of us had served as ambassadors before, some were career, some politically appointed ambassadors.

So, they keep it in a good mix. And what happened was that the plane comes to a stop and the door opens, and at the bottom of the ramp is Admiral William McRaven that, a couple of years before, had been the person that planned and executed the operation that killed Osama bin Laden. A larger-than-life figure in the American military. A larger than life figure. He was a Navy SEAL by his training. And he is still visible in today's world, even though he's retired.

I'm probably fourth in line. We start to get off the plane. The first person in line, McRaven introduces himself. The person says "Nice to meet you, sir." And then we carry on.

Once all eight of us got off the plane, McRaven gathers us around and says, "We've got to get something straight right from the start." And he's not being a jerk about it. He's being a teacher. He said, "I am a four-star Navy Admiral," he said, "but when I'm greeting you, you have a fifth star. So you're welcome to call me 'Admiral,' and you're welcome to call me Bill,'" he said, "but I call you 'sir,' and not the other way around."

He said, "That's the way our system works. Military authority always reports to civilian authority and you are the highest authority in your AOR, in your area of responsibility," he said. "So, there's nothing that the United States Special Operations Command will do there, whether it's a training exercise, a support exercise, or a black op, that you won't know about beforehand and have to approve. That's the way the system is."

And that's when I realized I was no longer in Kansas, Dorothy. This was a different world.

Don: Yeah. It truly is.

Well, so then you were in that position until the inauguration of President Obama's successor in office. So that was about three, three-and-a-half years?

Bob: Yep, exactly.

Don: Okay. Can you give us, we've been talking a long time now, so I don't want to get too bogged down, but maybe two or three examples of some of your more memorable experiences as Ambassador to Portugal.

Bob: Well, I'll give you an array of experiences.

You know, I think one of the things about the job is no matter what you think the job is going to be, it changes immediately. I thought I knew what my priorities were, going to Portugal, and then a couple of weeks after I got there, Vladimir Putin invaded Crimea. And you have a situation with Portugal, as a founding member of NATO, the issue is going to be: what's NATO's response?

There wasn't the same appreciation for what Putin was capable of then than there is now. And so, you had a divide within NATO. You had the countries in the east, the Baltic states, Lithuania, Estonia, some of the other states in the region, Romania, Poland, all thinking that Putin was not going to stop with Crimea and that he was going to push into their countries as well. You had the countries in the south, like Spain and Portugal and Italy, more worried about terrorism coming from the south, coming from Africa and north Africa.

NATO operates by consensus. You have to be, at the time, 28 for 28. You don't take a majority vote. It has to be unanimous, how you have to respond. Now it's 29 for 29 with Montenegro, and hopefully 31 for 31 when Finland and Sweden end up joining. So that becomes a negotiation right away.

You have to figure out, okay, how do you synthesize the interests of the countries in the south with the countries in the east to come up with a coherent position for NATO to take? And that means you're on the phone with your counterparts in those countries, trying to figure out what those interests are and making sure you work to align them.

Don: And you were doing that? You were on the phone with representatives from other countries?

Bob: My counterparts. With the ambassadors in those countries, trying to understand how are we going to find a way? So, I'm talking to the Portuguese government. I'm also talking to my colleagues, trying to figure out how can we move our individual countries to a position where we can get consensus? So, I'm off to that start.

A few months later, the Greek economy melts down. The largest bank in Portugal fails. And there's a worry from the U.S. Treasury Department that a worldwide economic contagion is restarting.

If you remember, in 2009, when President Obama took over, the economy was about to go over a cliff. It was still fragile by the time we got there. There was a European economic crisis. The so-called PIIGS were identified, Portugal, Italy, Ireland, Greece, and Spain, as being fragile economically, and that that would start the contagion. And so, the question was how do we stabilize the banking system in Portugal in order to keep a contagion from occurring?

Don: When you say "How do we stabilize," you're talking about how does the United States stabilize it?

Bob: Well, how do we collectively stabilize? And that's the real issue, because we in the United States have experience with that. We stabilized our own banking system, but you just can't call up the finance minister and say, "We're the United States. We're going to kind of solve this problem for you.”

On the other hand, we have experience that we can bring to bear. So, you have to figure out how do you get invited into the room in a way that you can impart that experience without making it look like your host government is incapable of handling their own problems. So that's a thorny issue to be able to navigate, which we did.

Then we have the rise of ISIS and the refugee crisis coming out of Syria and terrorists going to fight in Syria, coming back to Europe, and then disappearing within the Schengen zone, the zone that allows you to travel freely. And so, we were involved in trying to track down terrorists and trying to figure out where they were ending up within Europe. None of this could be anticipated when I got there.

On the other hand, one thing we did anticipate, in which my wife took the lead, was that when Portugal underwent it's revolution in 1974, at the time women not only couldn't vote, they couldn't travel without the permission of their husbands. By the time we got there, you had women graduating with MBAs in greater number than men. Women graduating with PhDs. Women were expected to not only take care of the children, but take care of the elderly parents. But they wanted to start businesses. They just didn't have the mentoring skills to be able to do that.

So, under the leadership of my wife, who had undergone similar kinds of mentoring in the United States, she cobbled together various elements of programs she had been involved in to create “Connect to Success,” where we got all the major companies in Portugal to take women on a year basis to mentor them. We provided free skills-based workshops. We provided networking events. And by the time we left Portugal we had 1,100 women business owners that had passed through the program.

And what they learned, more so than learning business skills, they learned confidence. They learned to be successful in business, you have to have confidence. You have to be willing to fail, which again was a problem in Portugal because failure was a stigma. But it's hard to be an entrepreneur and hard to be successful unless you're willing to risk it. So, we were teaching that.

And then the final thing that I'll mention is, I got great notoriety riding a Harley throughout Portugal. But again, it wasn't done simply for my recreational amusement. The State Department had a tendency to put out these very dry pieces on social media that nobody was following. Well, when I got on a Harley and I traveled around the country, we got a lot more notoriety. And then what would happen was local mayors who rode motorcycles would invite me to visit their community, not in the armored Cadillac that I was driving in wearing a suit, but with jeans and leather jacket on a Harley with my security detail around me.

And what became a better visual for the local mayor? You know, a couple of guys in suits, posing for a picture, or a couple of people on motorcycles with the mayor giving me a tour of the city? So, it got a lot more notoriety, and I fell in love at the time with riding a motorcycle, which I've kept up with to this day.

Don: Oh, I didn't know you were doing that.

Well, I could draw a direct line, I think, from Bob Sherman, going door to door in Iowa in 2006 and 2007, and Ambassador Sherman, riding his motorcycle around Portugal years later. I mean, you were connecting with the people. You weren't just going to the highest level. You weren't trying to put yourself in the position where, you know, you were being elitist about it and you just wanted to talk to the most senior influential people, powerful people. But you were connecting with people at all levels of the community. And I know you, or at least my impression is, that you became a very popular ambassador to the Portuguese, and in fact, received some recognition at the end of your stay there.

Tell me about your relationship with the Portuguese government, the Portuguese people, and Kim's too. I mean, I don't think President Obama knew when he asked you to serve in that role that he was really getting a two-for-one deal. And I know having the two of you as a couple added tremendous value to just having you as an individual ambassador.

Bob: Without a doubt. She was a rock star in her own right for what she was able to build, again, under the auspices of the embassy. But nonetheless was the driving force in that. And I used to remind the Portuguese all the time that they were getting two for one. So that became a steady joke.

But my view was that the Portuguese were a very formal society, a very hierarchical society in terms of, I mentioned, you know, the relationship between men and women going back in time. But their government officials were extremely formal and removed from the people.

My view was that, for a lot of the Portuguese, their view of the United States of America was what their view of me was. So, I used to say at the embassy, I'm not the ambassador to Lisbon, I'm the ambassador to Portugal. I want to get out of Lisbon as often as I can to really expand my role and to give people that view of the United States.

And as much as I could, I tried to interact on a level with the population. And I think that they appreciate it. They weren't used to seeing the United States Ambassador in a regular role, as they saw me. I went to all sorts of local events that were community based and community oriented.

I should say one other thing. Every country has a national day. Ours is obviously July 4th. And every country celebrates their national day. The smaller the country, the more definite it was that I was going to that country's national day. If I didn't go to the U.K.'s national day, well, the relationship is fine.

I did go. I went to every national day I could. But I made sure, the smaller the country, the more meaningful it was that the United States would take the time to honor them on their national day. And that was my physical presence at the event. And I would go and I wouldn't just drop in and drop out. I would stay, I would talk. I would do all of that, because my view was that I was the representative of the United States and also the representative of President Obama. And they were taking their cues both from the United States' point of view and from their view of President Obama, from how I acted.

Don: Bob. I want to turn a little bit to the aftermath. You served until the very end of President Obama's administration. I understand that at that time, U.S. ambassadors in a number of countries were asked by the incoming administration, or told by the incoming administration, they had to leave. Is that right?

Bob: Yes.

Don: Without there being time really to transition to your successor. So, you left at the very end, at the time of the swearing in of his successor. I'm not going to name him. I don't know why. I just don't want to make it about him.

And then you went back to private law practice, although I think your practice is very different now from what it was. I know you've been active in a number of other things. I know you have continued to be involved in Portugal. I think you're on the board of the Bank of Portugal, is that right?

Bob: I'm on the board of the bank that failed, that I mentioned before. What happened was we were able to stabilize the bank. That was in my role as ambassador. Eventually the bank was put up for sale. The Chinese, the Spanish, the Germans, and the Americans bid for the bank. I was the United States Ambassador, so I was promoting the U.S. private equity firm that was looking to take over the bank. They eventually got the deal. And eight months after I left as ambassador, they called and asked whether I'd be willing to join the board and help in the turnaround.

So that gets me back to Portugal once a month, or at least did before the pandemic. And now, I've resumed that. And I'm not just going back as the former ambassador, sitting in a bar with a whiskey or a glass of port, more appropriately, in my hand, reminiscing about glory days. I'm there for a business purpose. But it allows me also to keep the contacts and friendships that I've made. And there were many that fall into that category.

Don: And Kim is staying involved in maintaining those relationships she built in Portugal too, right?

Bob: As we're recording this, she's in Lisbon. She teaches now at Babson, after having sold her company. She teaches an international consulting course. And so, in addition to Portugal, she's involved in a number of other countries. But it just so happens, she's brought teams of students to Portugal right now to match with young businesses to help them grow. So, an offshoot of Connect to Success. So, she's there right now.

Don: What are you looking ahead at now?

Bob: Well, I can tell you Don, I've got a few more adventures left in me. What they are, I don't know. I can tell you that, as I just went through my career, I never would have anticipated any of the steps that I took. I don't know what the future is going to bring, but I do know that I'm not done yet. And we'll just have to do another podcast somewhere down the road so I can truly answer that question.