Mr. Kapp: This interview is being conducted on behalf of the Oral
History Project of the District of Columbia Circuit Court. The interviewee is
E. Barrett Prettyman, Jr. The interviewer is Robert H. Kapp. The interview took
place at the offices of Hogan & Hartson L.L.P. on the 3rd day of October, 1996,
shortly after noon.
Mr. Kapp: I am aware of the fact that sometime in the very early 60’s
you left Hogan & Hartson and entered the Kennedy Administration. I wonder if
you can tell us how it happened that you joined the Kennedy Administration?
Mr. Prettyman: I’d be happy to do that, although I probably ought to
mention two cases that I had just before I went in, if that’s okay with you.
Mr. Kapp: Yes, go ahead.
Mr. Prettyman: Simply because they were each impmtant to me for
different reasons. In 1962 I was appointed by the District Cowt to represent a
gentleman named William Fulwood, who was a Black Muslim at the Dist:Iict of
Columbia Jail, and this was now in the very early stages of the Muslim movement
among African-Americans. He had recently become a Muslim, and he was
attempting to have possession of the Koran and to wear Muslim medals and so
forth, and the prison authorities denied him that 1ight. We had extensive hearings
before Judge Burnita Matthews, who was a female judge from Mississippi, and she
held, I believe for the first time in this country, that indeed Muslims have the right
to practice their religion, to carry their medals, to have the Koran and so forth, in
prison, and she entered an order to the prison authorities to that effect. And that, of
course, has had wide-ranging repercussions since.
The other case was one that I argued just before I left the firm, and
that was my first case in the Supreme Court. As I recall, the Chief Justice called to
ask me if I would take that case, and it was quite an insignificant one in the law — it
probably has never been cited since — but it was called Andrews v. United States
and I, of course, agreed to argue it and did. I won that case on a very narrow issue
as to whether the Court of Appeals had jurisdiction over an attempted appeal by the
Government of a Dis?ct Court order remanding a matter for a hearing because the
defendants had not been given an opportunity to speak at the time they were
sentenced. I recall vividly that I was absolutely petrified before that argument
began, and in fact I thought I was going to get sick, except that the person who was
arguing in front of me sat down early and that got me on my feet and I was saved.
The Kennedy connection as I have outlined previously went back to
law school where I knew Bobby Kennedy, and then, of course, he subsequently
became the Attorney General. I got a call one day, I believe it·was from Lou
Oberdorfer, who was then head of the Tax Division at Justice and later a Federal
District Court judge, and he explained that the President and the Attorney General
were extremely upset about the 1113 Bay of Pigs prisoners who had been captured
and were in prison in Cuba, following the Bay of Pigs disaster, and they wanted
very much to get them back. In fact, even though we were well into December, they
wanted to get them back by Christmas. If the Government conducted this as a
Government operation, the stakes were going to go way up, and there were going to
be all kinds of difficulties and bureaucratic obstructions and all the rest. So they
decided to get together a small group of Washington attorneys, bring them down to
the Justice Department, and let them operate out of there, but operate as a private
venture. Jim Donovan, a New York attorney, had been negotiating with Castro over
the return of these prisoners, going to Cuba quite often. And now John Nolan was
going to join him on occasion, and I, and a few others, were going to be working out
of the Justice Department attempting to solicit the goods from around the country.
My particular job would be to obtain the transp01tation — the trains, the planes, a
boat, etc. — in order to get all of the donations from around the United States into
Oppalocka, Florida, and then from there on a ship and a few planes over to Cuba.
The negotiations were still going on, but the basics had been agreed upon. The
negotiations had started out with tractors and ended up with miscellaneous items but
principally medical supplies and baby food.
I gave up my practice within a few hours and moved into the Justice
Department, and we virtually lived there for the next ten days or two weeks. Then,
when we began taking care of the unbelievable number of problems that developed,
I moved to Florida and got myself a Holiday Inn room right near the Oppalocka
Airport and near the pier where the ship that I had gotten was going to be loaded.
When I say unbelievable problems, this has all been written about in books, but,
just as an example, we were going to send drugs to Cuba. If you were going to ship
even a single drug, you had to fill out voluminous forms, and there was simply no
way with this tremendous amount of material we were sending that we could
possibly have filled out all those forms, even if we’d had months instead of a few
days to do what we were doing. So we talked directly to the Government people
who were in charge of that, and we just cut through all the red tape and decided that
we’d use one form, one piece of paper, that would try to list every drug, and that
would be it. We’d just list anything that was going, and we somehow got approval
for that. It’s amazing when you’re working for the President and the Attorney
General what you can cut through if you have to.
Because companies were getting a tax break for the goods they were
donating, they caught on very quickly to the fact that they could get rid of a lot of
things in dead storage and send them to Florida and take a tax deduction. And
consequently, in addition to some wonderful supplies we were getting, we were also
getting a lot of junk. You know, everything from snuff to toenail clippers and
everything in the world, and that became quite a problem. Finally, Castro got wind
of the fact that he might very well be embarrassed by what was coming, so on the
night before the ship was going to sail for Cuba, he sent agents over in the middle
of the night. And I heard about this just before they got there. I went down in the
hold of the ship and had everything repacked, so that the good stuff was on top.
The agents arrived, and the press had no idea they were there, and as a matter
of fact never did learn they had been there. These agents looked things over in the
ship, and they thought everything was fine, but on the pier itself, because goods
were now coming in from all over the United States even as we were with them,
they saw some things that they definitely didn’t want. And they would go around
and say, “Well, we want this, but we don’t want this and we don’t want that.” But
basically they were pleased. They came back to my hotel room and called Castro
from the Holiday Inn and reported to me that they had told him that he was not
going to be embarrassed and that everything was OK. The police got those agents
out of there very quickly and sent them back to Cuba.
Well, the next morning, I got this frantic call from the pier, and our
people who were loading the ship said that they couldn’t operate like this, goods
were still coming in, and they didn’t know what to pack and what not to pack. They
didn’t know whether something had been approved or disapproved. There was no
way we were going to get out of there that day if we had to make a decision in
regard to each and every delivery. So I told them to just go ahead and pack
everything and we’d worry about it later. So they stored eve1ything on board ship.
And I called the Attorney General, and I said, “We have a little problem,” and l
explained to him that Castro was going to receive a lot of good materials but that he
was also going to receive some things that he definitely didn’t want. And in his
characteristic fashion, Bobby said, “Well, Barrett, you better go down there and
explain to him why.” And the next thing I knew I was on an airplane for Cuba.
We got down there, and Castro came out to the airport. Now the ship
had sailed but had not yet reached Cuba. So he and I had a nice discussion. I did
not bring up the problem I had been sent there to discuss. Instead, while he was
talking to somebody else, I said to one of his lieutenants, just making conversation,
“Where is Hemingway’s house from here?” And he said, “Well, it’s off here in the
hills. Would you like to see it?” And I said, “I’m sure I would, but I think I’d better
wait for the ship.” He disappeared, came back and he said, “Come on, Fidel wants
to take you.” So we piled into these cars with all these tommy guns and roared off
into the hills. We ?ved at Hemingway’s house, which was completely surrounded
by a locked fence, and we couldn’t get in. Castro was getting irritated, and these
agents were running all over the neighborhood trying to find somebody with a key,
and they finally found a gentleman who had been a kind of man-servant to
Hemingway for twenty years and had worked with him right up to the end. He did
have a key, and he let us in and took us through the house, which was exactly as
Hemingway had left it before he went off and committed suicide in the Western
United States. There was a bottle of booze on the living room table, and his weight
each day written on the wall of the bathroom, and the slats under the bed for his bad
back, and it was wonderful. We had with us one reporter, the captain of the ship,
the Surgeon General, and myself, plus some of Castro’s people. Anyway, we
ended up in the kitchen, where the TV was, and the man-servant told us how
Hemingway used to watch the fights in there, and they would bet on them. Castro,
who had been talking through an interpreter, began lapsing into English, somewhat
broken English. He talked about his relationship with Hemingway, embroidering it
significantly. As I learned later, he had met Hemingway only once. So it became
rather warm, and Castro was very tired but he blossomed a little and we got along
fine. We spent near1y the whole afternoon there, but we left finally and went down
the hills, and on the way back to the pier he suddenly stopped his car, we got out, he
walked out into this field, and there was a housing project over in the distance. He
just stood there, and then you could hear in the background somebody yell, “Fidel,
Fidel”. And then people began streaming out of the housing project, and we were
soon surrounded by hundreds of people, and he introduced us. Back down now to
the pi?r, and they’d started to unload the ship, and fortunately almost the only thing
you could see was baby food. It was just right up to the sky, and he was elated, and
he ordered that the prisoners could start to leave right away, and in fact I think a
flight might have gone out that night. But as a result of the way it developed, I
didn’t have to do a lot of explaining. I did get in the fact that because of the way we
had to load, he might be getting some things he could throw away, but by then he
was sufficiently pleased with what he’d seen. So we spent a rather wild night at the
Havana Libra, and in the morning I was on a plane out of there.
That was one of the most emotional scenes I’ve ever been in. I was in
this plane, a little prop job, and it was revving up down at the end of the mnway,
and we couldn’t take off because MIGs kept coming in and landing and taking off.
While we were sitting there, this car careens around a comer and out to the plane,
and the captain of the ship has just found out that the families of the prisoners — so
we’re talking about thousands of people — are going to be released too, and they
were going to go back to the States on his ship. He was almost hysterical because he
had, you know, a couple of toilets and no blankets, and there were going to be
pregnant women and grandmothers and everything in the world on this ship. So I
got him calmed down and told him we’d send food, blankets and medical supplies
for his ship, and just to take it easy. So then our pilot went and revved up the
motors again. There ?ad not been a sound on this plane, not a sound. But when the
wheels left the ground, pandemonium broke out. It was just wild. People laughing,
screaming and crying, hugging you and breaking out cigars and all kinds of things.
It was a very, very emotional time. When I got back it was Christmas Eve, and the
President had us flown in a jet to Washington, and then he had a car take me to
Baltimore, where I was going to spend Christmas with my then-wife and her family.
A day later, the President called to thank me personally. So I thought that was the
beginning and the end of my experience with the Kennedys. · ·
Unfortunately, Bobby got the impression that because I had dealt with
the transportation aspects of this venture, I was somehow a transportation expert. I
knew absolutely nothing about transportation. But he called and said he had this
problem at the Justice Department, where the people in his Antitrust Division who
were supposed to be dealing with railroads and other transportation problems were
not even speaking to the people at the ICC and other agencies who were supposed to
be handling the same problems, so everything had come to a standstill. It was a
mess, and he asked me if I could come in for six months to be his Special Assistant
to get this all straightened out. So I said I would, and I left the practice and became
a Special Assistant io the Attorney General, theoretically to work on transportation
problems. I say “theoretically” because as it developed, there were all kinds of other
things to do as well. But what I did about transportation was a petfectly simple
exercise. I simply got everybody in a room. I mean, I brought in heads of railroads,
I brought in the chief people at the Antitrust Division, I brought in expe11s in the
field. l just sat down with them, had a series of meetings, found out what the
problem was, and wrote the Attorney General a memo with recommendations. And
in three months it was all over, everything was fixed. So I made plans to go back. I
had no plans to make my future with the Government? I wanted to get back to
Well now, of course, Bobby was convinced [Laughter} that I was the
leading transportation expert in the United States, which was ridiculous, absolutely
ridiculous, because I really knew nothing about it. But he said that the President
needed advice in this area in the White House, and would I go over and be a Special
Assistant, particularly since the eastern railroads were in a chaotic state right then
— the breakup of the Penn Central, and so forth. So I agreed to go as Special
Assistant to the White House. I had an office in the Executive Office Building, and

although I did indeed deal with transportation matters — and in fact I was the
President’s representative on the Interagency Committee on Transport Mergers — I
also spent a lot of time on a myriad of other matters — anything that happened to
occur to Bobby. For example, if he had thirty minutes suddenly open up in his day,
he’d call me and I would call a local high school and tell them we were on our way,
and he and I would go out to an inner-city school here in Washington. He’d walk in
on classes, or if they had time to get kids together in an auditorium, he would talk to
them all about staying in school and how important the future was and how
important education was. Which the kids of course just loved.
He also thought that it was horrendous that there were so few play
facilities in the worst sections of town, and he got the idea that we ought to build a
playground with donations. So I found a whole city block up at 7th and P Streets
NW that was being used to store abandoned cars — whenever the police would haul a
car off the street that wasn’t claimed, they would just throw it into this block. So we
had the cars taken out, and I got 0. Roy Chalk interested in it, and we began building
a playground. And since we didn’t have much money, I got things donated, such as a
fire truck, where you could climb up into the seat and slide down. And of course the
usual basketball hoops. We built a soap box car roll, where you could roll down a
long slide. We got trucks. The largest vehicle ever cairied on the streets of
Washington was donated; it was a huge tugboat, and we had a tenible time getting
permission because when they cairied it past the Capitol they were afraid it was
going to fall into the subway that Congressmen use to get back and forth from their
offices to the House and Senate. What I thought would be the hardest item to obtain
turned out to be quite easy. I very much wanted an airplane in there, because these
kids in the neighborhood, of course, had never been anywhere near an airplane. I had •
been told that in order to get a used airplane, you had to wait eight years. There was
a long, long waiting list for these planes, because there was a great demand and not
that many of them available. I called an Air Force general from the White House and
told him that the President and the Attorney General were interested in this
playground and in ge?g a plane in there. And he said, “Well, how many do you
want?” [Laughter] And I said, “I’ll take two,” doubling my ambition, and he said in
this very apologetic voice, “Mr. Prettyman, I am terribly, tenibly sony, but I don’t
think we can get them there until Thursday.” And I said, “Well, if that’s the best you
can do.” [Laughter] So on Thursday we had the two airplanes, and it really was
getting to be a very, ve1y wonderful playground. When we were building it, Bobby
and I took Cary Grant out to see it. He was in town for a Stay-In-School Benefit that
Ethel Kennedy and a group ofus had engineered. Needless to-say, he got a lot of
Not long after the playground was completed, President Kennedy was
assassinated. I believe that the first public event that Robert Kennedy attended after
the funeral was the opening of this playground. I remember there was one humorous
aspect of that. He wanted to walk there and back from his office, and we were
very fearful. If you remember that period, those were nervous days. We didn’t know
what was afoot as to whether there were a lot of assassins out there or what not. So
we were going to have a lot of police with him, and he said he did not want any
police with him. He didn’t like to have police around, so we dressed the police up in ,
civilian clothes [Laughter], and the pictures of him walking back show him and his
huge dog, Brumus, and then these people who looked very ill at ease in their tightfitting
suits, who were all policemen.
But in any event, we had something like 10,000 kids at the opening of
this playground. Yo? couldn’t get in there. It was just incredible, wondeiful. That
story has a very sad ending, in the sense that later, as kids began to get hurt — as they
do on all playgrounds — the city began to get nervous and began closing vruious
features down, so that the next thing you know it was a ve1y sterile place. It’s still
there, and technically it’s still a playground, it still has a plaque with the names of the
people who had contributed, but it’s not what it was, and it’s all very, very sad.
The other thing I was engaged in with Bobby during this time was a
pool. One of the schools we visited was Dunbar, and while there we saw a beautiful
indoor swimming pool that they had closed down. And he wanted to know why it
was closed, and they said that they didn’t have any money to repair it. So he asked
how much it would cost. And they said something like $35,000. It had been closed
for over a year, and you can’t imagine how this hits a Kennedy mind. The police
told us, after all, that when that pool was open, the crime rate was way, way down,
because they opened it even in the evening. Parents, as well as kids, could come to
use it. It was always used, so there were virtually no criminal offenses in the
neighborhood, and as soon as the pool closed, the crime rate shot up. And here for
lack of $35,000 they were allowing this pool to remain closed. So Bobby told me to
get the money, get it open. What I did, I called up a Catholic bishop here in town
and told him that a Jewish group and a Presbyterian group were each going to
contribute, and I needed $10,000. And then I called a Jewish rabbi and told him the
same thing, and I called a Presbyterian minister, and so indeed they all contributed.
We opened up that pool and Chuck Connors, “The Rifleman,” came to the opening,
and the kids of comse loved that, and we made a big to-do of it. But that was the
kind of thing I did.
I also got this idea that since Bobby was so interested in kids staying in
school, we ought to have an open letter to school children from their sports heroes,
and we drafted a letter directly to the children saying that you’ve got to stay in
school, this is important, here’s what it will do for you. If you-drop out you probably
won’t be a success, and so forth. I just ran across these letters the other day. I
thought nothing of it at the time — they were stuck away in an old box — but here
are letters from Mickey Mantle, Maury Wills, Rocky Marciano, A.mold Palmer, Stan
Musial, Jackie Robinson, Gene Tunney, Wilma Rudolph, Y.A. Tittle and, you
know, just a whole group of great sports figures of that time giving their permission
to use their names. And so we distributed this in the schools.
Mr. Kapp: Was your impression of the Attorney General changed in
any way during this period?
Mr. Prettyman: Yes.
Mr. Kapp: Could you talk about that a bit?
Mr. Prettyman: Well, I did not have that clear a picture of him early on
because while I had seen him quite a bit down in Virginia, we were both working
hard and the only time I saw him socially was when it was connected with an event,
such as a Legal Forum dinner. I had the impression of a pretty conservative fellow
who didn’t do terribly well in his classes, but I had no distinct impression of him as a
personality at that time. As I got to know him, I suppose he changed more dming the
course of my acquaintanceship with him than anyone else I ever knew. It was like
watching a flower grow in fast forward. You could see changes eve1y day. He
learned. He absorbed information. He had a great deal of empathy once he became
aware of a problem. He was not aware of the extent of poverty even here in
Washington, much less throughout the country, until he traveled and saw it. He was
not aware that his own Justice Department had practically no Negroes in it, as we
called them then — Blacks and African-Americans today. He changed that very
quickly once he found out, but at first he didn’t know. There were so many things
that he did not know because he had led a fairly sheltered life, with a ve1y, ve1y
well-to-do father. But he learned and he cared, and there was nothing phony about
that. He really woke up to things that were going on and that ranged all the way, as I
say, from poverty to Vietnam, where he was slow coming to realize the nature and
extent of what we were involved in. But once he understood, he spoke out. So I
would say that my impression of him changed dramatically, and particularly in the
later years, when I helped with his Presidential race, I got even stronger impressions
of him. Because in the meantime, while a Senator, he had changed some more, had
learned a lot, had espoused new issues and had become a fuller person. He had
become a completely integrated whole, a fascinating man. l guess the most
interesting political animal I ever knew because, like Nixon, he was basically shy,
had very little small talk, concentrated on his duties, worked hard, always wanted to
be doing something, accomplishing something, and yet he had people wild about him.
I mean I’d never seen anything like the crush that we ran into when we ultimately
started his campaign.
I might tell you one little vignette about him {laughter], which says
a lot. When he was running ultimately, and I realize we are pushing ahead here
in time, but when he ran for President he was worried about the fact that
businessmen despised him, hated him, feared him, and he talked to me about it,
and I told him, first of all that I would draft an article that he could nm in Business
Week or some place like, making people less fearful of him. l did that, and it was
published with him on the cover. And I said the other thing I’ll do is strut bringing
distinguished business people by to see you, one at a time, so you can just chat
with them, and they will see that you don’t have two heads, and the word will get
out that maybe you ‘re not as bad as they had thought. Great idea. So the first
person I brought in was the then-President of Capitol Records. We represented
Capitol Records, ancl I didn’t have time to talk to him before the meeting, but I met
him in New York and took him up to the U.N. Plaza, where Bobby had an
apartment. And we went in and sat down, the three ofus, and I waited for the
conversation to begin and there was dead silence. Bobby just sat there, had no
idea what to talk about, and I realized that the President of Capitol Records wasn’t
even sure why he was there — his name was Livingston, a wonderful guy, but he
couldn’t figure out what was going on. And so I had to finally break the silence
and get small talk going, and it was terrible. It was just awful. Finally, I showed
Livingston out [Laughter], and in the hall he said, “What the hell was that all
about?” [Laughter] And that was the last business person I brought by to see the
Presidential candidate.
But Bobby was very courageous. One day when he was in the
Senate, he, Ethel, some of their children, another couple and I went on a sailing trip
in a borrowed boat. A big storm roared up and in the middle of it a Coast Guard
cutter came as close to us as it could — not very close — and a voice over a bullhorn
announced that Bobby’s daughter Kathleen had been injured by a horse. Bobby
jumped overboard into a terrible surf and disappeared. Thank God he turned up
and somehow got to the cutter. The seas were so bad that the cutter’s front window
shattered on the way back, and the boom on our boat broke.
I was also there in Steve Smith’s New York apartment when the
decision was made that Bobby would run for President. That was funny because
we were all sitting around debating what we should advise him to do when he
walked in and announced he was going for it.
Mr. Kapp: When you were in the White House did you have any
substantial contact with the President?
Mr. Prettyman: Very little, very little. We’d see him at meetings and
a couple of times in the hall and things like that, but no, I didn’t deal one-on-one
with him hardly at all. Virtually all of my work was with the Attorney General and
through Mike Feldman.
Mr. Kapp: Just going back one step here to your day in Havana. Did
you develop any kind of impression of Fidel Castro as a result of that contact?
Mr. Prettyman: I am ashamed to say that the overwhelming
impression I had was that he wasn’t going to be with us ve1y long. I really thought
that the display of guns, his tiredness, he just struck me as a man on the way out,
and of course here we are 30 years later, and he’s the one who’s still around. All the
rest are gone. I would never have guessed his durability. He is an intelligent man, a
man I think very aware of himself and history, and in fact with an inflated idea of
himself and history. He had a great deal of pride, and l thought the way he spun
out the Hemingway connection was interesting — the fact that he would bother to
make that relationship a lot closer than it had in fact been — why he did that is
interesting to speculate about. But based on that short experience, I can’t give you
an in-depth analysis of him but I certainly had an impression of a leader who I
thought was in some trouble but in charge, no question about that.
Mr. Kapp: You were in the White House at the time of the
Mr. Prettyman: I was in the Executive Office Building, I had placed a
call to someone on th? Hill and I can’t for the life of me remember who it was, but
as soon as I started to talk they said, “No, no, don’t worry, we know all about it.”
And I said, “What do you mean?” And they said, “About the President being shot.”
And that was the first I’d heard. It had just happened apparently, and I put down the
phone and walked across the street to the White House — you know, there’s a little
roadway there between the Executive Office Building and the White House — and I
walked in and it was like a death camp. It was just awful. People were crying and
sitting and staring, and there was great confusion. I remained there and was there
when Lyndon Johnson arrived in a chopper late that evening, and walked over to the
President’s office. I remember very well, and I tell you as shocked as everybody
was by the original news, the sight of him as President coming to the President’s
office was, if anything, a greater shock. It brought the whole thing home in a way
that nothing else could have.
Mr. Kapp: Did you continue on in the White House after Lyndon
Johnson arrived?
Mr. Prettyman: I think I was either the first to resign or certainly very
close to it. I did not know Johnson. He did not know me. He wouldn’t have been
interested in any of the things I was doing. As you know, he and Bobby did not get
along, and of course I had no interest in getting into government in the first place. It
had all just been a series of flukes. And so once I saw the situation, I got out and
went back to the practice.
Mr. Kapp: When you originally went over to become pru.t of the
Administration, you worked on a series of railroad issues. Did that have any
influence on your subsequent law practice?
Mr. Prettyman: Well, it did in the sense that it got me involved in one
or two matters which in turn lead to a number of other matters. The first one, I
think, was on behalf of Western Pacific Railroad, and among the first things that
came up was a case that they had in the Supreme Court. I worked on that, and then I
worked on some extensive hearings involving the Western Pacific. I lived in
Chicago at a hotel for almost a year where these ve1y strange heru.·ings went on in the
Hilton across the street. I lived in the Blackstone Hotel, and the hearings were in the
Hilton because there were so many lawyers you couldn’t get them into a hearing
room, so we had to hire out the main ballroom of the hotel to have our hearings.
The hearing examiner was a wonderful gentleman but an alcoholic, since
-15 ldeceased,
and so we would start late in the morning and quit early for lunch, and
come back late from lunch, and quit early in the afternoon. So it was tremendously
expensive for everybody involved. He eventually broke his leg one night and was
replaced by another hearing examiner who was very strict. Finally, the two of them
sat together and disagreed on almost every single ruling. But as a result of all this,
the case went on and on. It was almost a perfect example of how you should not try
a regulatory case. But it was very easy living for me. I would get up late, have
breakfast in bed and wander over to the hearings, and I would cross-examine
somebody maybe on’:e a week, [Laughter], and it was an easy life, and I got to
know and love Chicago. A great town. But, as a result of those hearings, the
General Counsel of the Rio Grande Railroad, who paiticipated in the hearings, later
got me involved in hearings involving the Rio Grande. Then that railroad was
eventually bought and bought again and ended up as the Southern Pacific, with a
very wealthy gentleman owning it, and so it led to a series of cases that are still
going on in the firm. We have been involved in a lot of railroad work, all coming
out of that one little hearing with the Western Pacific.
Mr. Kapp: You said that you had resigned from the Administration
shortly after the arrival of President Johnson and I know that you returned then to
Hogan & Haitson. Can you tell me a bit about the nature of your practice on your

Mr. Prettyman: Well, I became a partner in July 1964. I had now
argued several cases on appeal, and it had become clear to me that my heart was
really in the appellate area. This is something I’ve always loved. To take a
confused record, including all the mistakes that might have been made below, and
somehow shuffle it up and recreate it into a coherent story and a coherent argument –
– this appealed to me tremendously. Incidentally, during this period in the mid-60’s
I had one of the strangest experiences I’ve ever had as a lawyer. I had been
appointed to represent a Miss Johnson, who had been picked up at 2-3 o’clock in the
morning on 14th Street in Washington flagging down cars. And instead of being
charged with soliciting, she was charged with vagrancy. One of the key phrases in
the vagrancy statute was “leading a profligate life,” and I attacked the statute on
about eleven constitutional grounds, including the fact that nobody knew what it
meant. So at the trial, whenever anybody came to the stand, no matter what they
were going to testify about, I would ask, “By the way, what does ‘leading a
profligate life’ mean to you?” And of course the answers were all across the
spectrum. Most people had no idea, and even if some people ·gave a wild guess, it
was usually off the mark. But the policeman who arrested her said, “Well, I think it
means doing something, you know, partially bad, kind of bad, over a period of
time.” And I said, “What do you mean by that? Do you mean like going out to the
race track all the time?” And he said, “Yeah.” And I said, “Betting on the horses on
a regular basis?” And he said, “Yeah, that’s right.” And I said, “Well now, I
understand that J. Edgar Hoover goes to the races on a fairly regular basis and l
assume he bets when he’s there. Would you say that he’s leading a profligate life?”
“Yes, sir, I would.” [Laughter J Now this is in Superior Court, and of course the
Washington Post never covers run-of-the-mill cases in Superior Court. But with my
luck, on this particular day a reporter who had been covering another hearing had
wandered into the courtroom and just happened to be there when this occurred. The
next morning, there’s a little piece in the Post about Hoover leading a profligate life.
I had two FBI agents in my office at 9 AM when I anived for work, and
they handed me a letter personally signed by J. Edgar Hoover in which he excoriated
me for gratuitously injecting his name into a case by referring to his numerous visits to
the race track. He said this was an unwarranted use of his name to obtain some cheap
publicity. He continued: “The facts are that I only attend the races — an entirely legal
pastime [Laughter] — on Saturdays and then infrequently. I am usually one of 20,000
persons present, which include officials — Federal and State — and of all branches of the
Government. Why you should single me out of this large number can only be that you
are vindictively inclined or are hard pressed to make a point completely irrelevant to the
true merits of your case. In any event, I do not appreciate such despicable use of my
name” [Laughter] Well, needless to say, I almost had a heait attack. [Laughter] I
wrote him back and tried to explain that it was a great compliment, because I was trying
to show that leading a profligate life could not possibly be what this officer thought it
was, since the very reputable J. Edgar Hoover did what the officer thought leading
a profligate life was all about. But needless to say, I never heard back from Mr.
Hoover. [Laughter] That was quite an experience.
I had some other cases at the time that were quite interesting. I now
started getting a series of Supreme Court cases. I ended up arguing 19 of them, and
I would love to get ti.umber 20, but I don’t think I will. And these cases were all
over the place; they dealt with no particular subject. I wa? getting some First
Amendment work. I should also mention Jones v. Wolf, which was a seminal
church-state case in the Supreme Court. I did some work both for free and for pay
for the Reporters’ Committee for Freedom of the Press. I was also beginning to
represent some writers. For example, I represented Katherine Ann Porter for about
the last 20 years of her life. I worked closely with Charles Alan Wright and Clark
Clifford on the TWA case for Howard Hughes — a case we won in the Supreme
Court. And I represented Hughes, along with Seymour Mintz and others, in the
Clifford Irving matter, when we put Hughes on the phone with a Time reporter to
prove that the recluse had never heard of Irving. I represented Rita Hayworth for
two years to prevent her from being taken advantage of by the media while she had
Alzheimer’s, and I met with the Aga Kahn and talked on the phone with Orson
Welles about her situation. I represented Yasmin Kahn at the same time. And at
another point I successfully represented a Boston Globe rep01ter accused of
masterminding the Indian revolt at Wounded Knee. So I’ve had some interesting
clients, including Lloyds, the Methodist Church, Fotomat, the National Wildlife
Foundation. I once did an internal investigation of Olin Corporation to determine
whether one of its subsidiaries had been illegally shipping arms to South Africa.
And I have already fold you about the TV documentary on the death penalty that I
did with Truman Capote.
Mr. Kapp: Was Capote himself involved in the interview process?
Mr. Prettyman: Oh yeah, yeah, he was. In fact he was supposed to
do all the interviews .. The problem is that some of these prisoners had a very
adverse reaction to him because of his mincing ways and refused to talk to him, and
I ended up doing a lot of the interviews. I think as it ended up, he probably did half
and I did half. But he was present during all of them. As I have mentioned, we
ended up in California interviewing then-Governor Reagan.
So my work was quite eclectic, quite varied, and there didn’t seem to
be any constant theme to it except that, as I say, the appellate work gained my
attention more and more and I began to focus on it. One interesting case I should
mention was called Jackson v. United States. and again I was appointed by the D.C.
Circuit. Some of my most interesting cases, I find, have been those where I was
appointed by the court. It was the case of a man who murdered his wife and
assaulted another man when he found his wife and the other man in bed together.
We somehow discovered that sitting on the jwy was a man who previously had had
an affair with a manied woman whose husband had caught and killed her. The
juror had never revealed that. And we got the D.C. Circuit to reverse the conviction
on the ground that it was an unfair trial to have on the jwy a juror who had
undergone precisely the same type of experience that was being tried to that jwy.
Amazingly, the panel that unanimously reversed included Wilbur Miller, who I
don’t think ever again voted to reverse a criminal conviction; Burger, very
conservative; and Tamm, also conservative. So I always felt very proud of that
Mr. Kapp: What in your mind makes for good appellate advocacy?
What would you say about that?
Mr. Prettyman: A complete knowledge and understanding of the
record. Serious and long thought about a cohesive the01y of the case. You’d be
surprised how many people do not have a total theory of their case, and by that I
mean a theory that is so complete that it will answer hypotheticals thrown at you in
oral argument. Let me give you an example. The case of Plyler v. Doe was a case
in which Texas had by statute denied a public education to undocumented alien
children. And during the oral argument in the Supreme Com1, the fellow
representing the State of Texas was asked by Justice Marshall, “Could Texas deny
those children fire protection?” He stammered around and finally said that he had
no idea. I don’t understand that. I don’t understand how anyone approaching an
argument in that case would not know that you ‘re going to get questions about fire
protection and police protection and all the other things that a state normally
provides for its citizens. How could you not know that? He did not have a theory
of his case. It didn’t make any difference whether the answer was yes, they could
deny fire protection, or no, they couldn’t, so long as he had some reasoning to back
up his conclusion, but he had to have a cohesive theory of the whole case so as to
show what the state could do and could not do and the reasons for it. Now that’s
what I mean by a cohesive theory of a case.
The other important element in preparation is to step back and look at
your case from your <?PPOnent’ s standpoint and from the standpoint of a judge who
wants to vote against you. So many advocates refuse to do that, because it’s
unnerving; they don’t like to face the unpleasantness of realizing that they have
holes in their cases. But all cases do. When I begin preparing, I strut writing
myself questions. They could be factual questions. They could be legal questions.
They could be hypothetical questions. Anything that I don’t immediately know the
answer to. It’s not uncommon for me to have over 300 questions by the time I get
through the record. Those are questions that I want to have answers to before I
stand up in Court.
I also have at least one moot court, and the purpose of that is so that
others can throw questions at you that you haven’t thought of. No matter how well
prepared you think you are, there’s nothing like having an entirely different mind
directed at your case. Even strangers to the case will come up with questions that
you have not thought of. One of my most vivid memories is of a moot court. We
had a new associate at the firm who’d only been with us a few days, and I invited
him to the moot court just to make him feel part of the firm and so that he could see
what a moot court was all about. And low and behold, I was arguing away when he
put up his hand and.said, “Well Mr. Prettyman, suppose that church had been sold
to an unwitting buyer and this happened and that happened and so forth?” And I
was absolutely stunned; it was a wonderful question. I had not thought of it. I had
no answer to it at all, and I had to say so. Well, I had about a week to go and
needless to say, in the shower and in bed at night and in every other spare moment I
was thinking about that question, and I finally came up with not a pe1fect answer
but the best that I could co11.jure up, and by golly I got all through the actual oral
argument and was halfway to my seat when Justice Stevens said, “Mr. Prettyman,
suppose that church had been sold to an unwitting buyer?” {Laughter] Almost in
the same words that this kid had asked the question, and I was able to roll off my
answer, very assuredly, giving the answer I had prepared, and sit down. But you
know, if the associate hadn’t asked me that question, I’d still be standing there.
You learn from that, so I don’t agree with advocates who say that moot courts take
away their spontaneity. Quite the contrary, I think it gives you much greater
spontaneity because you’re more sure of yourself, you’re more relaxed, you know
the type of things that will be coming at you, and you ‘re better prepared.

I think another thing is self-assurance. One of the things I so admire
in John Roberts, one of our partners, is that once he finds out what side of the case
he’s on, he becomes absolutely certain, absolutely totally certain, of the rightness of
his position. You cannot tear him loose from it, and he approaches that argument
as if there could be no answer other than the one he has. I admire that because it
gives pause to the judges who are opposed to that view, and it gives assurance to
the judges who are on his side, and it’s a good attitude.
Certainly it takes intelligence to be a good advocate. You have to
understand the ramifications of your case, you have to understand where dissenting
Justices may be trying to take you, what they’re trying to set you up for in order to
disprove their position to other Justices. You have to know when and where to
concede and when not to; you have to know whether a question is friendly or not,
and it’s not always clear. I heard one judge say that you’d be surprised how many
advocates fire on the lifeboats coming to rescue them. You know, that lawyers act as
if every question has to be hostile, when of course it’s not.
The broad view is just terribly important to see the case in context. It’s
not just this little factual situation. This has ramifications for other unrelated cases,
other areas of the law. You’ve got to see how it all fits in. You’ve got to make
sure, therefore, that you’re not plucking away for a theory that the Justices can’t
possibly buy because it’s going to get them into trouble elsewhere. You’ve got to be
realistic. You’ve got to know which instincts to appeal to and which to stay away
from. It takes a very whole person to be a good advocate, I think, and of course you
have to be articulate.
Mr. Kapp: Have you got a view as to the relative importance of the
written brief and the oral argument?
Mr. Prettyman: There’s no question the written brief is the most
important element. It’s all there, or it should be. It’s the first thing the judge sees,
it’s the last thing he sees if he’s writing the opinion. And if you have not convinced
the judge by the time he or she has read your brief, you’re probably in trouble. On
the other hand, I have. had a surprising number of judges tell me that in a surp1ising
number of cases they have in fact changed their minds. I have heard the figure go as
high as a third of argued cases, which I am inclined to question. But I’ve at least
heard that. Judges and Justices have said, time and again, that they find oral
argument extremely important, even if they do not change their minds; it often
affects how the opinion’s going to be written. It’s going to affect what issues are
going to be dealt with and at what length. A lot of judges say that they really did not
have that clear of an idea of where they stood when they came on the bench, and
oral argument helped them decide. So it’s not just changing minds; it’s helping
them make up their minds. So I think it is imp011ant. It’s also imp011ant because
many people lose cases. More people lose cases than win cases. By that I mean,
they go in and either wholly fail to make their point or make a concession that they
should not have made, and they thereby help convince the court that they’re wrong.
So —
Mr. Kapp: You don’t subscribe then, totally to the canard that cases
are never won in oral argument but are frequently lost in oral argument?
Mr. Prettyman: I certainly don’t agree that cases are never won, but I
do think that more cases are lost than won. Yes, I do agree with that. But it seems
to me you have to take the word of the judges. Lawyers are not very good judges of
how judges reach their conclusions. You have to listen to the judges themselves,
and most judges would say that oral argument is important. It may not be important
in a couple of southeastern states where the judges have drafted their opinions prior
to the oral argument. No, it’s not going to make much difference at all. But in cases
in the Supreme Court, and I think in most circuit courts, argument can be extremely
helpful, and you should always ask for it.
Mr. Kapp: What in your mind makes for a —
Mr. Prettyman: Excuse me, you should always ask for it if you are the
appellant or the petitioner. I don’t mean that you should ask for it if your opponent
who is seeking appellate review does not ask for it. Excuse me, go ahead –
Mr. Kapp: What in your mind makes for a well-crafted appellate
brief? Can you describe your approach to brief writing?
Mr. Prettyman: Clarity, succinctness, accuracy, a little bit of a flair -and
I don’t mean off the wall, I just mean the judges read so many hundreds of
thousands of pages that if you can be interesting, they love it — when it’s something
that is well written and can catch their interest. They like a cohesive story instead of
a jumbled presentation where they can’t really tell what happened. They love
honesty, and this is particularly true in oral argument when you confess that there’s
a particular point that worried you when you got the case and you found the answer
and you hope that answer is satisfactory to the court. That’s very appealing. But
they love it when you deal directly in your brief with a very tough point, rather than
ignoring it or, even worse, distorting it. If you can get their attention, if you can
give them a reason, both in terms of fairness and justice and in terms of precedent,
that they should decide for you, then you’ve come a long way toward getting to a
favorable result.
Mr. Kapp: When you start on an oral argument, do you ordinaiily
have some particular goal or objective in mind? I mean obviously you’d like to win
the case.
Mr. Prettyman: Five votes!
Mr. Kapp: Right. [Laughter] But there’s not any sort of generalized
approach in that sense?
Mr. Prettyman: I don’t think so. You have figured out in advance
where your most likely votes are coming from if you’re going to get any, and
particularly if it looks close you probably have a pretty good idea of who is on the
fence, where the key votes are. So you want to say things that ai·e going to appeal to
the decision-makers, the two or three that are going to make the difference. But I
really can’t say that there’s any kind of generalized approach that you have in mind.
You’re just trying to give the best damn argument you can. Look, if you’re in
college and your roommate wants to go see one movie and you want to go see
another but you want to go together, I mean you start in with an argument: Yeah,
but the stars are over here, and I heard the plot was fabulous, and this director also
directed this other great movie, and you come up with every single argument as to
why you want your roommate to see this other movie. It’s no different in oral
argument in court. Y_ou are trying to convince. You are t:Iying to make someone
who either has no opinion or has an opinion against you rule your way, to give them
every reason why they should. The whole game is to persuade. You can’t persuade
if you are not aiticulate. You cannot persuade if you don’t have down-to-earth and
important grounds supporting you. You can’t persuade if you unfortunately have
the kind of personality that judges don’t like. There are a few advocates around who
are so arrogant that the judges start in hoping they can decide against them.
[Laughter] That’s not very persuasive. But other than that, I-really can’t say that
there’s some shiny key to all this.
Mr. Kapp: Any difference in approach between an argument before,
let’s say, the D.C. Circuit on the one hand, and the Supreme Court on the other
Mr. Prettyman: There are certainly big differences. With the Circuit
Court, assuming that you are not en bane so that you have only three judges, you
should know how they have voted in the past on matters similar to this one so that
you can gear your argument pretty much to what you think their views are. You
obviously have fewer questions. There are fewer hypothetical questions at the
Circuit Court level, because the judges of course are bound by Supreme Court
precedent. If you have anything in the Supreme Court that supports you, you
obviously want to make that argument very strongly, and in fact the oral argument
may hinge on what ?at Supreme Court precedent means. What’s the application
here? In the Supreme Court, you have nine people coming at you instead of three.
You have more questions, you have more complicated questions, you have more
hypothetical questions because the Justices want to know where you ‘re taking them
and what the implications are for the law generally — whether you ‘re getting them
into hot water, because, after all, there’s nobody around to correct the situation if
you do. The personalities, of course, are different, just as they are from panel to
panel on the Circuit Courts. But personalities are very important. You have some
judges who can’t stop asking questions. You have some judges who never ask
questions. And you have everything in between. So knowing your cow1 is really
quite important.
Mr. Kapp: Tell me what you think about the influence of amicus
briefs. Do you think that they’re generally useful, not particularly useful, can you
generalize about them?
Mr. Prettyman: If it’s an amicus brief from the Solicitor General, it
can be extremely important. Extremely important. Sometimes that importance
cannot be overstated. If it is an amicus brief from a large group of states, it can be
very important. Sometimes an amicus brief from, let’s say, a medical group in a
case involving a technical medical procedure could be very important. It gives a
different viewpoint, a.pd it makes the Justices feel at ease in an area that they really
don’t know too much about. My own feeling is that (a) it almost never hwts to have
the support of an amicus b1ief; (b) most amicus briefs are not worth ve1y much; but
(c) they don’t really do much harm. So I encourage them in cases where you can get
them — at least from responsible people. You don’t want just any screwball writing
in on your behalf. But an authoritative organization all the way from the NAACP to
the Chamber of Commerce, depending upon the case, I think can be of help, and the
Court has referred to these from time to time. If you were to take a typical Term and
look at all of the amicus briefs filed, my guess is that not over 10% made much
difference one way or the other.
Mr. Kapp: What about the Circuit Court level?
Mr. Prettyman: You see very few of them, because Supreme Cowt
precedent plays such a big role there. That’s an interesting question I’ve not
thought much about it because I haven’t seen that many of them, but I would guess
that the import is lesser. I’ll ask a circuit judge about that sometime.
Mr. Kapp: Maybe there’s a difference between an en bane case and a …
Mr. Prettyman: Could be.
Mr. Kapp: … case before a panel?
Mr. Prettyman: Yeah, could well be.
Mr. Kapp: Can you talk about cases that you’ve handled in the Circuit
Court of Appeals for the District of Columbia? Any particularly memorable cases in
that court?
Mr. Prettyman: Well, one very unfortunate one was U.S. v. Western
Electric, where I was arguing for the telephone companies, and I was up against
Larry Tribe. I made my argument, a tough point in a tough case, and Tribe got up
and engaged in a long, long exchange with Judge Silberman. And it went on so
long, way way past his argument time, that when he sat down I did something l had
never done before in my career; I got up and asked if I could have some extra time.
Judge Mikva was acting as Chief Judge, and he declined. And I lost on my key
point; I lost the case. But I’ve always felt that that was basically unfair. It was one
of those rare instances where Tribe went on so long — everybody talked about it
later — that I should have been entitled to a little extra time. That was a very tough
case. I argued the Teleprompter case here. One wonderful case I had did not get
to the Court of Appeals. We got the first restraining order against the SEC
when we were representing Nelson Bunker Hunt, and it was in the middle of his
Silver difficulties. That matter was settled after we got that restraining order, which
the agency had not really heard of before.
Another case that was in the District Court rather than in the Court of
Appeals was one involving John Lennon. I was representing Capitol Records on an
on-going basis. John Lennon very late one night had gone into the Club Cavalaro
in New York City and had sat down at a table. There were about six people at the
table, and one of them was a Morris Levy. Levy was somebody who ran one of
these record companies that put albums out on television; they are not distributed in
the general market. You buy them only through television. And John Lennon sat
down and began talking about a record he was then making of his oldies favorites,
songs that he’d grown up on and was now redoing in his own style. But he was not
terribly happy about how it was going, he was down. So Morris Levy said, “I’ve
got the answer for you. Let me put this album out on television. It will make the
same amount of money, if not more, and you won’t get pilloried by the press the
way you would if you put it out through the regular commercial market, because
they don’t review the stuff that comes out on television.” Now everybody present
agreed up until that point that that is what happened. But then one group said that
Lennon replied, “No, no, I’m under exclusive contract to Capitol Records and I
can’t do that. I don’t mind sending you a dummy tape just so you can hear what
I’m talking about, but there’s no way I can let you put it on TV.” The other
people at the table swore that he said, “That’s a great idea. I’ll send you the tape
and you go ahead and put it out.” Well, Lennon in fact sent a rough dummy of the
uncompleted tape to Levy, and the next thing he knew an album was on television,
being sold. As soon as Capitol Records heard of this, it sent telegrams to all of the
TV stations around the country, threatening suit if they didn’t stop immediately,
and Levy thereupon sued Capitol Records for interference with his rights. The trial
centered around what had been said — whether there was an oral contract. And as I
say, half the people at the table swore one thing, and the other half swore the
opposite. Although I did not represent John Lennon, I was on the same side as he
was, representing Capitol Records, so his attorney and I went to his home, the
Dakota, the large building that he was later shot outside of.
Mr. Kapp: Oh in New York, yeah.
Mr. Prettyman: Yeah, in New York. We went there on several
occasions to prepare him for his testimony. And I must say, I didn’t like John
Lennon at first. I thought he had a very casual attitude toward the lawsuit and a
casual attitude toward everything, I guess. But the more we went on, the better I
liked him. By the time he got to trial, he was nicely dressed, and he had a pitcher
of what appeared to be orange juice with him every day, which he put down under
his seat. He and Yoko Ono came together and attended eve1y day of trial, and we
really became pretty good friends. One night, for my book collection, I rushed
around Greenwich Village and found a book called Lennon Remembers, and I
brought it in the next day and he inscribed it for me. He made a wonderful witness.
He was one of these witnesses who, if the answer wasn’t going to hurt him, he
would give it straight out — hard, narrow, clean, articulate. If it was a question he
didn’t want to answer, he’d start in and you’d get totally captivated by what he was
talking about, and he’d go on and on and on and by the end of it you forgot what
the question was. [LaughterJ He never even came close to answering it. He was
also funny at times, he was street smart, was what John Lennon was. John Lennon
was no intellect, but he was street smart as hell, and as I say, I ended up liking him
quite a bit.
Mr. Kapp: How did the case come out?
Mr. Prettyman: The trialjudge, who almost didn’t know who the
Beatles were because he was a great fan of opera and serious music, had several
children who were insane about the Beatles, and he told us later that he went up
about thirty notches in his kids’ estimation just by the fact that he had had this trial.
He ruled that John Lennon had not made an oral contract, that he was perfectly
aware of being under exclusive contract to Capitol Records and would never have
given away his record rights and did not do it. So he ruled with one half the people
at the table. {LaughterJ
This concludes the interview held on October 3, 1996