A Conversation with E. Barrett Prettyman
(Appeared in Bar Report, April/May 1997)

The first president of the unified D.C. Bar, E. Barrett Prettyman Jr. is a native Washingtonian who fought with the Ninth Army during World War II, received an undergraduate degree from Yale, and worked as a reporter on the Providence Journal before attending the University of Virginia Law School. After clerking for three Supreme Court justices, Prettyman joined Hogan & Hartson where an appellate work practice was frequently interrupted by stints of public service: as Special Assistant to the U.S. Attorney General and Special Assistant to the White House during the Kennedy administration, and Special Counsel to the House Ethics Committee during the "ABSCAM" investigation, among other posts. A former president of the PEN/Faulkner Foundation and second president of the American Academy of Appellate Lawyers, Prettyman is the author of Death and the Supreme Court, winner of the Mystery Writers of America Edgar award for best fact crime book of 1961. He has argued 19 cases in the U.S. Supreme Court and cases in most of the Circuits.

Bar Report: What was it like having a father who was D.C. Corporation Counsel, chief judge of the U.S. Court of Appeals, and for whom the U.S. Courthouse was recently renamed?

E. Barrett Prettyman: It was wonderful. I admired my father tremendously and tried to follow in his footsteps in the sense that he was a reporter who became a lawyer and I did the same thing. He always seemed to be proud of the various activities in which I was engaged.

BR: Was it assumed that you would go into law?

EBP: No, I really assumed I was going to be a reporter forever. I loved working for the Providence Journal. It was a great experience. My most interesting story was when there were rumors about Mafia gambling operations in Newport, but they couldnít seem to find out where any of this was located. I went under cover, grew a beard, put on old clothes, and lived like a rat in Newport for weeks. I finally located the place down near the wharf. You went up some steps, there was a hole in the door and—just like in the old movies—if they recognized you they let you in. I followed somebody in, and it was a big gambling operation. When the fellow came out and asked who wanted to throw the dice for the winning numbers of the day, I stepped forward and threw the dice. I very excitedly called my paper, and the editor said that was pretty good but we better have a witness. He sent another reporter to join me, and it took a number of nights to get back into the place. I threw the numbers again. We wrote a huge front page story about how the attorney general couldnít find the criminals, but the Providence Journal could. Then people began following me, and I got out of town quickly and back to my regular job and regular attire.

BR: Why did you leave the paper?

EBP:It was fascinating work, but I was starving. I decided I would go to one year of law school and then return to the paper and ask for a substantial raise, because I would now be a constitutional "expert." Instead, I fell in love with law school and never thought about going back.

BR: Why did you choose Virginia?

EBP: I wanted to be on the East Coast, I thought it was an excellent school, and I also thought I had a better chance of becoming a big fish in a small pond: I might get lost at a Harvard or a Yale. And I did intend to come back to Washington. I was born here, grew up in nearby Maryland, and I always loved the city. I loved the politics of it, the culture, everything about the place. I never had any question about that.

BR: Did you meet Robert Kennedy at Virginia?

EBP: Robert Kennedy was two years ahead of me. We got to know each other because he was head of the Legal Forum which brought speakers down. In the usual Kennedy fashion, he decided he would choose who would be the president after him and even two years after him. He seemed to think I would be good at that, and we became friends early on. He used to have me over to the house to meet an eclectic group of speakers—it would be Justice William Douglas one week and Senator Joseph McCarthy the next. We had some fascinating sessions.

BR: After law school you went to the Supreme Court where, we understand, you are only person who ever clerked for three justices.

EBP: I donít know whether thatís true or not, but it was certainly unusual and purely circumstantial that I ended up with three. I interviewed with Justice [Robert H.] Jackson, and at the end of it he told me I could have the job if I would be his only clerk. It took me about five seconds to decide that one. At the end of the first term he asked me to stay over for the second term, and I agreed. But he died in October 1954, right after the Brown v. Board of Education decision came down. I was getting ready to leave when Justice [John M.] Harlan, who had been appointed to replace Jackson, asked if I would stay on with him. But it took him almost five months to get confirmed, and during the interim period, because I had been rather close to Justice [Felix] Frankfurter during my first term, I was an extra law clerk for him. I ended up the second term with Justice Harlan after he came aboard.

BR: What were the differences between the justices?

EBP: Justice Jackson was a loner with a great sense of humor. He loved to gossip, and the personal relationship was very important to him. Frankfurter was more of a friendly gadfly, in a sense. He had no children of his own, and the law clerks were his children. He loved the law. He was in my office a lot during the first term, proselytizing me because for some reason he thought I might have some effect on Jackson—which was just not true, but he chose to think so. Justice Harlan was more the lawyerís lawyer, from a big firm in New York, not interested in the personal side so much. I do not think I would have qualified as his law clerk if he was just selecting out of the blue because he wanted the most highly intelligent people he could find. I got to like him tremendously, particularly after the clerkship, but there was no fooling around, no gossip with him, while we were working.

BR: How did you wind up at Hogan and Hartson?

EBP: I came here because Stan (later Judge Stanley S.) Harris, a classmate of mine at Virginia, had come to the firm in 1953, when I went to the Court. He had been very happy, and he persuaded me that this was the place to be. One of the people who would become a mentor to me, Joe Smith (Joseph J Smith Jr.), had a very serious Section 7 antitrust case that he was handling alone. He promised that if I came here I would be putting people on the stand within a matter of months, which is exactly what happened. I probably should have been disbarred—I had no idea what I was doing—but that was a great enticement, to get quickly into the practice.
     I learned later that the senior partners had a big argument over me, and that "Nubby" [Edmund L.] Jones argued that if I didnít turn out right, there was no way for the firm to get rid of me, since my father was on the D.C. Circuit. And I always thought he was right, because Iím still here.
     When I started there were about 28 lawyers in Hogan & Hartson’s only office. Now there are 460 with offices all over the world. I started out doing almost exclusively antitrust—that first Section 7 case lasted 13 years before we finally won it in the Fifth Circuit—but I ultimately figured out that I wasnít that suited to antitrust. In the meantime, the Supreme Court itself had appointed me to a case, and it began to occur to me that appellate work was my forte. Thatís where I ended up, in a wide variety of fields, no particular specialty.

BR: What was your first Supreme Court case?

EBP: It was Andrews v. U.S., a Section 2255 case that I have trouble remembering except for how frightened I was when I got up there to argue it. When I first rose to my feet, I heard a sound. I looked up to see what it was, and Justice [Byron] Whiteís lips were moving. I thought to myself, "Thatís interesting. Heís asking me a question and I have no idea what it is." When he got through, I gave an answer that had absolutely nothing to do with the question. He looked at me peculiarly and let me go because I guess he figured I was just hopeless. I heard all the questions thereafter, but to this day I have no idea what he said.

BR: How did you happen to write Death and the Supreme Court?

EBP: I wrote what I thought was a book about a fascinating case my father had had, the only time he ever sat as a trial judge. I turned that into a publisher, Harcourt Brace, which said it wasnít a book, it was a long magazine article. In fact, I later converted it into an article for the ABA Journal ["Wiser In His Own Conceit," 51 ABA Journal 450 (1965)]. But they said, We like your writing, we know youíre familiar with the Supreme Court, and weíd like to have a book about how the Court works." When I had been at the Court, I had been most fascinated with the death penalty cases that came through. They really caught the Courtís attention. It was totally unlike the way it is now, where the Court is handing down denials of stays of execution almost every week. In those days these cases were unusual, and the justices spent a tremendous amount of time on them. I decided to write a book about how the Supreme Court worked, using the death penalty as a backdrop. I read every death penalty case written during the lifetime of anybody still alive. Then I investigated those cases to see what had happened since. I selected six, really on the basis of their endings: some people were executed, some walked out free, and everything in-between.

BR: We understand the book led to a TV documentary?

EBP: Yes. I represented Katherine Anne Porter for the last 20 years of her life, and I was with her at a function in New York where she was receiving some kind of award. Truman Capote came up and said he had been about to call me. He was going to film a documentary for ABC called "Death Row, USA," and he needed a lawyer to get permissions from prisoners and lawyers and wardens and all the rigmarole involved in getting into these prisons. The reason he was looking for me was that Smith of Smith and Hickok—the killers in [Capoteís] In Cold Blood—had made him read my book.
     We went around the country and interviewed people waiting to be executed, as well as then-Governor Ronald Reagan, [later Judge] Skelly J. Wright, Professor [Ernest] Van Den Haag, [Ohio] Governor Michael de Salle—people who had views about the death penalty, both pro and con. After we finished the project, top leadership at ABC changed and threw out a lot of the work that had been done by the old guard, including this documentary. Truman was beside himself. They told him it was too morbid, too grainy, people wouldnít watch it. That documentary has never to my knowledge been shown in this country. Now ABC canít find it; various people have called me to try to locate it, and itís just gone.
     It’s a shame because of the interview with Reagan alone. When we went to his office, it was close to lunchtime, and he said, "Letís do this later." We went out to his house and had a two- or three-hour lunch where we all drank wine and had a great time. Then we went back to his office, and the interview went well until I questioned him as to whether, since he was in favor of the death penalty, he would favor having executions on television. That came pretty close to ending the interview. He said that he would not favor it, but when I pressed him as to why—because wouldnít that have the most deterrent effect of all?—he just said he didnít think it would be appropriate. I donít think he liked the question; he thought it was antagonistic, although that was not my intention.

BR: Describe your role in the Cuban hostage negotiations.

EBP: After the Bay of Pigs disaster, Castro had 1,113 prisoners—invaders who had been captured—in some horrible prisons down in Cuba. President Kennedy felt responsible for them and wanted very much to get those prisoners out. He and Bobby Kennedy got hold of Jim Donovan in New York who negotiated an exchange whereby Castro would get millions of dollars worth of medical supplies, baby food, and miscellaneous items in exchange for the prisoners. They got Donovan because he was a private attorney and they knew that if the government negotiated on its own, the price would be exorbitant.
     To continue the facade, they enlisted a small group of us attorneys to move into the Justice Department. My responsibility was transportation—getting all these supplies from around the country to Florida and then over to Cuba. The problem was that companies received a tax deduction for these goods, so they were emptying their warehouses of everything from snuff to outdated canned goods and shipping them off to Florida. Castro got wind of this and was concerned that he was going to be embarrassed, so he sent three emissaries over to Florida. We heard they were coming, so we kind of repacked the bottom of the ship to put all the good stuff on top. When they got there, they called Castro from my motel room and told him he was not going to be embarrassed. At the same time, they gave us directions about the goods they saw on the wharf—to send this but donít send that, etc. Bobby Kennedy was anxious to get these people out by Christmas, and we only had a few days left. It became clear that there was no way we were going to figure out which supplies to send, pack the ship, and get it all going on time, so I just ordered everything packed and put onboard ship. The ship sailed, and when I called Bobby and explained the problem, he said, "Well, Barrett, you better go down and tell Castro why he’s getting all that junk." The next thing I knew I was on a plane to Havana.
     Castro came out to the airport. We had a nice chat, but I did not mention the junk goods. Trying to make conversation, I asked one his lieutenants, "Whereís Hemingwayís home?" He said itís up in the hills, disappeared for a few minutes, came back and said, "Fidel wants to take you." We piled into cars with Tommy guns and roared up into the hills. We got to this place with a fence around it, and it was all locked up. Castro was getting pretty frustrated, his men were running all over the neighborhood, but they finally located a guy who had been Hemingway’s manservant for 20 years and who had a key. We spent the afternoon there: Castro, the surgeon general (because we were sending so much medicine over), a reporter, and me. Finally Castro was in a lot better mood, and we went down the hills to the wharf. The ship had arrived, and as far as you could see there was baby food.
     Castro thought it was great. I explained that he was also getting a lot of stuff he didnít want, and I explained why. He took it very well. He ordered that the prisoners would be released starting the next morning. We had a merry night, and the next day I took off with a planeload of prisoners. By then Castro had also announced that the families of the prisoners who were in Cuba could also leave. When I got back it was Christmas eve, and the President had a plane that took several of us back to Washington. It was very moving, about the best Christmas I ever had.

BR: How did this assignment segue into Special Assistant to the Attorney General?

EBP: Because I had been informally in charge of transportation for all these goods and supplies, Bobby Kennedy got the impression that I was a transportation expert—which I was not. He had a problem at the Justice Department in the sense that the people in the Antitrust Division dealing with transportation were not speaking to the experts at the Interstate Commerce Commission. He thought I, as his special assistant, could work this out in six months. Within three months I figured out what the problem was, wrote him a memo making recommendations, and got ready to come back to practice. This convinced him more than ever that I was an expert on transportation. The country was having a good deal of trouble in the Eastern corridor, with railroads particularly, so he asked me to go to the White House as the Presidentís adviser on transportation, which I did.
     Of course, you have to realize that when you worked for the Kennedys you never did just one thing. In fact, you normally didnít do the thing you were principally assigned to do; you did everything else but. With Bobby, for example, he was very interested in kids staying in school, trying to do something about crime. Part of my time was spent taking Bobby to schools at the drop of a hat. If he would suddenly find a half hour he didnít expect to have, Iíd call a school, they’d get an assembly together, and heíd lecture the kids on the importance of staying in school.
     We did all kinds of good works, and then of course there was the Presidentís assassination. I was either the first or one of the first to leave after that. I didnít know President Johnson, and he didnít know me and Iím sure he had no interest in what I was doing. I was really not there to be in government anyway; I was simply there because I had been asked by Bobby to be there. So I came back to the firm.

BR: What was the firm’s attitude toward your government service?

EBP: This firm has always had a very good attitude toward public service. They felt that so long as the job was adequate, that it gave you some depth and experience, then you ought to do it.

BR: How did the D.C. Bar presidency come about?

EBP: It was right out of the blue. Marna Tucker, later the first female president, called me and said it was very important that the Bar get off on the right foot. They wanted a couple of people who had judgment, who would be recognized as possible leaders of the Bar, and would I run. I did not think I was going to win, because I was running against a well-known local trial practitioner. I think my own name was well known in part due to my father, but I certainly had not done a lot of trial work.
     In any event, I did win and found myself in the middle of a cauldron. We had no members at all one day and 15,000 the next. We didnít quite know what the rules were, and we just winged it. I did go to several ABA meetings where sections were devoted to involuntary bars, but I did not have as clear an idea as I had later about the restrictions that were inherent in such a bar. One example was a criminal case in the D.C. Court of Appeals where I thought, and my board thought, that a matter of fairness and justice had to be asserted by somebody. I wrote an amicus brief, and we just filed it. We couldnít do that today.

BR: Twenty-five years later, how is the Bar doing?

EBP: I have mixed reactions to it. I think itís wonderful that the Bar has grown as it has—from 15,000 to some 66,000 members—that its basic structure is the same, that the board is still vibrant and really cares about the affairs of the Bar. The fact that the ethics committees are on the ball and working hard, and all kinds of committees are functioning and carrying on their duties, and that thereís so much continuing legal education is marvelous. It is a good, strong, healthy Bar.
     On the other hand, I must say that some of the strictures that are placed upon it are understandable but in some respects unfortunate. I think the Bar could do more work and be more effective if it had a bit more leeway in terms of acting for the Bar as a whole. I understand it, but if you’re asking me how it could be stronger and more effective, the 66,000 would say to the board, "We trust you, we know you will act on our behalf with good judgment, and therefore represent us to the hilt."

BR: Whatís the biggest challenge facing the Bar today?

EBP: I don’t know that I could select one but I could select several. One, of course, relates to seriously confronting the issue of how people who are without adequate funds can afford the system. I have people coming to me all the time who, for example, have been libeled or who are outraged at some offense and who want to assert their rights. You have to ask them if they can really afford all those depositions, all that discovery, and the eventual trial. Even assuming that theyíre right and that a jury might award them damages, can they afford the process? The answer is no; the vast majority of them simply cannot afford to protect themselves. I donít think the Bar is doing enough to address that problem.
     I also think that the Bar is paying very little attention to what is happening in the legal profession today, in the sense that we have more and more lawyers but fewer and fewer firms. Large firms are getting larger, and some of the smaller ones are dropping off, so that we are going to end up with these huge conglomerates. This is not necessarily a bad thing, but it is different, and somebody should be looking at whether there are ways to ameliorate the potential harms.
     I think also that the Bar does not do enough to protect and enhance the interests of judges—who really cannot defend themselves very well—in terms of their salary scale, their facilities, and the kind of attacks going on right now, where some congressmen are talking about impeaching judges who have a different philosophy. Judges cannot really step up to bat on that, but lawyers can and, I think, should be reacting strongly to that threat.

BR: What do you like best about practicing law?

EBP: I love to be confronted by problems and to figure out how to find solutions. Letís say that this afternoon they were to bring into my office 5,000 pages of record from a trial a client had lost and say, "OK, take it on appeal." I love to become creative and develop something nobody would have thought of and then make the most effective argument. Iím fascinated by the whole business of persuasion, whether itís talking somebody into going to the movie you want to see, or into voting for your client in a major Supreme Court case. How you articulate the points that you choose to make, and what points you choose to leave out, the personality that goes into it—I find all of that absolutely fascinating.
     The bottom line is that despite the size of the Bar, despite all the problems with the Bar, despite the publicís image of lawyers, it’s just one hell of a great game. This is so much fun, particularly to practice law in Washington. It used to be that you had to be in New York to practice big time, but thatís not true any more. Most major disputes end up in Washington in one form or another. To get a handle on that and to be involved in some of these matters, large and small, is so interesting. I haven’t regretted a moment of it.