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The Man in the Gray Hat

The formerly controversial Gene Iredale embraces nuance and theft

Published in 2015 San Diego Super Lawyers magazine

By Erik Lundegaard on January 21, 2015


Q: Let’s start off with a couple of quotes on your website. One is from The San Diego Union-Tribune: “Just the mention of Eugene Iredale’s name in courthouse circles touches off controversy.”

A: That’s from a very old article. I’m afraid I’m not as controversial as I used to be.


Q: What was it in reference to?

A: I handled a lot of criminal cases that were significant cases in the federal court, and the nature of the cases would be such that there would be immediate disagreement and strong feelings on both sides of the issues.


Q: Immediate disagreement … from the public?

A: No, from the prosecution. For some time, federal prosecutors were not used to being challenged, and they felt that they had the right to a certain deference, just by virtue of their position as prosecutors.


Q: Are you more deferential now?

A: That article was written when I was young—33 or 35—and when you’re young you think you know everything. When you get older, you become much less intelligent. I have a slightly different philosophy now about how to handle things and how to deal with people.

There was a judge that we had here in San Diego named J. Lawrence Irving. He was appointed by President Reagan, and he sat on the bench for eight years; then he resigned because, among other things, he found the federal sentencing guidelines inhumane and unfair. He was a person who had a great influence on how I perceived things. What I found was that many times, when you can attribute something to either malice or misunderstanding, it’s normally misunderstanding. I would see people come before Judge Irving, and he was so amiable and decent with everyone that both sides would walk out of the courtroom feeling they were properly treated. I still marvel at how he did that.

You don’t have to be aggressive or mean or hard-nosed. You can be a good person. You should let your conduct be governed by the exigencies of the client’s legal need and the way the other side approaches you and deals with you. Many lawyers are really rational, decent people. Others have various problems.


Q: So back then, was it a tendency of yours to see things more in a black hat/white hat way?

A: Completely black and white, without nuance, and I was fighting for the white hat. Normally federal prosecutors like to position themselves on the side of justice, decency, everything every right-thinking human would adopt. Sometimes in doing so, they have to do things or deal with witnesses, such as informants, who are actually the antithesis of the values that they are espousing in court. So I would fight for the right to wear the white hat. That, I think, caused some controversy.

As a practical matter, that still goes on. But what I found is that when you fight for something, you can still remain an amiable and decent person.


Q: So how long did it take you?

A: To learn these lessons of common human decency and politeness? About three decades.


Q: [Laughs] The other quotation is also a bit old. It’s Justice Thurgood Marshall in Wheat v. U.S.: “Mr. Iredale had proved to be a formidable adversary. … Were I in petitioner’s position I’m sure I would want Mr. Iredale representing me too.” A footnote, right?

A: It was a footnote. The case had to do with a prosecution in which I represented one defendant, and with the agreement of the second defendant and of the first, represented the second one. I went to trial, and we won the case for the first guy and resolved his case. Then we had the case of the second defendant, and I got a good resolution for him. Then the third defendant, Mark Wheat, wanted me to represent him, and the prosecutor objected.

This was an issue that had been kicking around in the Supreme Court years before—raised in an earlier case called Flanagan v. United States. The issue is the following: If in a case where there is a potential conflict of interest, but all defendants waive their right to raise that issue in order to obtain counsel from the lawyer they choose, is it appropriate for the court to permit that? The Supreme Court unfortunately disagreed by a vote of 5 to 4. They said, “Even though there is a waiver from all defendants, the court nonetheless possesses a residual power, or an inherent power, to disqualify a lawyer not only for actual conflicts but for serious potential conflicts.” Rehnquist wrote the majority opinion, Marshall dissented.


Q: And in his dissent, he was very complimentary to you.

A: Yes. Because the idea is if a lawyer knows the case or if the lawyer is particularly adept in this field of law, then shouldn’t the clients have the right to make a reasoned choice?


Q: Is that common? For a U.S. Supreme Court justice to compliment a lawyer in a decision?

A: No, I really lucked out. I lucked out because it’s rare that you’ll see a case that is about a lawyer …


Q: In a positive sense.

A: In a positive sense. The majority said: Well, he may have been a good lawyer, and that can be considered, but that’s not dispositive. The dissent, especially Stevens, said: Look. The role of the lawyer in defending the rights of citizens is central to our system. The decision in Wheat, which denigrates that right and which, in a sense, substitutes the judge as the person who makes a judgment for the defendant, in a sense a parochial judgment, is not an appropriate way to treat the adversary system.


Q: Sounds like you still disagree with the decision.

A: Well, I understand the considerations. What could be, on the one hand, a rational decision by both A and B to promote their joint interests by using the same lawyer who has familiarity either with the case or the court or the procedures, can in fact be, sub rosa, a manipulation by A to lean on B to remain silent, to avoid testifying against A, or to avoid problems by having the same lawyer for both by putting the lawyer in a position where he cannot hurt the interests of either in order to help one particular defendant.

So I understand the rationale behind the decision. So maybe our proposed rule was somewhat too narrow. That is to say, you want it to be a completely free, voluntary and intelligent choice by both defendants to go with the same lawyer, but that requires some inquiry. Nonetheless, with that caveat, I think two defendants should have the right to elect to waive their right to have separate counsel—if, in their assessment for whatever reason, including their strategic decision about their likelihood of getting a good result, it serves their interests. They should be the person that decides that.


Q: So you would still be on your side.

A: I would, but I wouldn’t be so vehement about it.


Q: Why criminal law for you?

A: When I was coming out of law school, we had just gone through the Vietnam War and Watergate. I had graduated from a school where most of the graduates, despite the general political climate, were going to work for large firms whose clients were corporations and very wealthy people. I had become oriented in my thinking toward left-wing causes.


Q: Why?

A: It was the zeitgeist.


Q: But why personally for you?

A: Can I tell you something? So many of these things are based on psychological dynamics and your own individual psychology. In my life, in my development, I was the oldest of seven children, and I always had problems with my father. So that transfers to a general anti-authoritarian view. We have a very good bench here in the Southern District of California. But when I first started being a lawyer, I would be so outraged in my tone, when the judges who were on our bench were simply doing what was reasonable and fair.


Q: Any particular incident stand out?

A: I remember a motion to suppress. The motion to suppress was denied, and I began to quote William Pitt to the judge: “‘The poorest man may in his cottage bid defiance to all the forces of the Crown. It may be frail; its roof may shake; the wind may blow through it. The storm may enter but the King of England dare not enter. All of his force dare not cross the threshold of the ruined tenement!’ So to, in this case, the entry into the trunk of Jose Antonio Esquivel contravenes the fundamental principle of individual autonomy protected by the Fourth Amendment!”


Q: And his reaction?

A: The judge began to blow his nose vigorously.


Q: I thought he would be impressed that you could quote William Pitt verbatim.

A: Not so.


Q: What did your father do?

A: He was a personnel manager at a small manufacturing concern. My father was not a bad person. I suppose my place in the birth order and the things that I saw that happened made me feel that he was being unfair. He was unfair, I thought, to my mother, to my siblings. I just didn’t like that.

All my life, I’ve hated bullies. So often, you see certain things happening in court, especially where I come from, where we represented people from Mexico, many of whom were poor, many of whom were illiterate, who were hauled into federal court on charges, and most of whom were motivated by simple economic necessity. So it inspired me to do things, in standing up, that I think was the right thing to do, but may have been fueled by an excessive zeal and somewhat less dispassionate analysis than was called for.


Q: Where were you born and raised?

A: Louisville, Kentucky. I went to Columbia College in New York. Then I went to Harvard Law School.


Q: How did you wind up in San Diego?

A: I wanted to work for a public defender’s office, and I had an interview. I left Boston, where there was a foot of snow on the ground, and landed in San Diego. When I got off the plane, it was a balmy 68 degrees. The palm trees were being kissed by a gentle breeze, and I said to myself, “This is where God wants me to serve His poor.”


Q: Was that with the Federal Defenders of San Diego?

A: Yes. I worked there for six and a half years, and became, for the last 18 months, their chief trial attorney: assigning cases and working on supervision of the other lawyers and helping with the administration of the office. The executive director ran the office, and he is just a fantastic man: John Cleary. He has really dedicated his life to knowledge and to improving both himself and the world. At age 50, he started to learn Russian. Then when he was in his 60s, he taught a comparative criminal procedure course at Moscow State University. Now, he’s in China for his study of the Chinese language, and he’s starting to teach a course there.


Q: What did you learn from him?

A: He was just an ideal boss. Before he took over the office, there were two or three appeals in the space of a year. He took over, and it increased by a factor of 10. He increased the emphasis on advocacy, on professionalism, on appropriately zealous representation of people who needed zealous representation. He would always support his staff.


Q: You’ve taken 160 cases to verdict. How many do you do a year now?

A: Some years, I don’t do any. Other years, five or six. Unfortunately, in both civil and criminal cases, there’s a tendency for fewer cases to actually go to trial. I think that is a terrible thing.


Q: Because?

A: First, because it’s important for the country, for the society, for the polity, to have these issues aired in open court and decided by a jury. Second, in order to determine or gauge what is an appropriate settlement in a case, you have to have tried similar cases in the past so you can understand what is the likely outcome. Third, it’s a terrible thing, and it’s very demoralizing for lawyers, especially young lawyers, not to be able to slug it out, to fight a case, to litigate the case. To actually understand the dynamic of presenting your case. To be forced to translate what you want to say into what makes sense. To speak in such a way that it is clear and appropriately convincing to people who make the decision.


Q: We hear this a lot. “More and more cases are settling. Fewer cases are going to trial. It can be a danger to the justice system.”

A: It is a danger. Not can be. Is.


Q: What can be done to reverse this trend?

A: First, lawyers have to realize that it’s important to try cases. Even if you lose a case, it’s all right. There are prosecutors who will say this: Sometimes it’s better to lose a case than to sell it away too cheaply.


Q: That’s tough if somebody’s freedom is on the line, I guess.

A: But your freedom is never on the line. It’s always an issue of… Do you take four years to avoid eight? Do you take 10 to avoid 20?


Q: Earlier, you talked about the difficulty of Mexicans getting a fair shot in the justice system. Do you think that’s still true?

A: I think that people from Mexico are coming into their own. On the other hand, you look at the population that we have here in California. There is a danger that the disproportionate distribution of wealth, which is a national problem, is aggravated here in California. Because you also have a population of people, many of whom are undocumented and who cannot properly assert the human rights and the statutory rights that they would otherwise be able to assert, and are therefore subject to an extra level of oppression or exploitation. That can create a bad situation.


Q: An older case of yours, People v. Marron, got overturned as a result of racist jury comments.

A: There was a guy on the jury who said any Mexican with a gun is guilty.


Q: Sounds anti-NRA.

A: It managed, at the same time, to offend enthusiasts of the Second Amendment and people who are against racism.


Q: Which case are you most proud of?

A: [Pause] I represented a border patrol agent, Sergio Lopez, who was doing an undercover operation in Chula Vista, California. Now, mind you, he had waist-length hair, he was driving in an unmarked car, and he properly used his flashing lights and siren going through some intersections as he tried to get back to a position where he was conducting surveillance. But the Chula Vista Police Department didn’t like his attitude. So when he got out of his car and said, “Hey, what the hell are you doing? I’m a federal agent. We called you guys,” they decided that they would throw him to the ground, causing him to aggravate a neck injury, and threaten to tase him—even though they knew he was a border patrol agent. They kept him in handcuffs, seated on the curb to humiliate him for about 40 minutes. We asked the jury to return a verdict of $1 million, but they were so outraged by the conduct of the police department that they returned a verdict of $2.2 million.


Q: What cases are you working on now?

A: We have four wrongful death cases in the office now. One is Anastasio Hernandez Rojas, who was killed by repeated tasings after he was handcuffed and on the ground at the port of entry in San Ysidro.


Q: You also represent powerful people—like Mayor Maureen O’Connor.

A: Yes. It was actually a very tragic case. Maureen O’Connor was one of the finest mayors San Diego has ever had. But after she retired from being mayor, after her term was up, her husband, Robert O. Peterson, who was the man who founded Jack in the Box, died. She was all alone. Unbeknownst to her, she was also developing a brain tumor, which was in the part of the brain that governs impulse control, among other things. So she began to gamble very heavily and lose. Ultimately, she went through about $20 or $25 million.


Q: I thought it was a billion-dollar gambling problem. That’s what I read.

A: That’s what the government wanted for the press release. It’s a billion dollars in net losses, but $975 million in net gains.

What happened is she took $2 million from a foundation that was set up by her late husband, and of which she was the trustee, but it’s not as though she embezzled the money. She was there, and she wanted to pay the money back. But whether it was actually a federal crime is highly questionable. So we agreed to defer the prosecution for a period of two years. She has made payments that she can toward the tax debt and will make payments, if she can, toward the payment of the loan back to the foundation. But in any event, so long as she does the best she can and stays out of trouble, we’ll have the case dismissed next year without a conviction.


Q: Have you ever disliked any of your clients?

A: Yes, but very few.


Q: Why?

A: There’s a natural impulse on the part of the client to cooperate with the lawyer and the lawyer to help the client. Part of it is financial from the lawyer’s point of view, but part of it is that you genuinely develop a relationship. You read things, and in the abstract, you say, “Oh my God, look at this charge. How could somebody do that?” Then you find it’s not quite what is presented, or maybe it’s not factually correct. Or even if it is factually correct, there’s an explanation, or certainly there’s mitigation.

So instead of judging people, if you just listen to them, sometimes you’ll be able to find that what Solzhenitsyn said is the truth: that the dividing line between good and evil runs not between countries or social classes or political parties, but through the heart and soul of each and every person in the world.


Q: That’s fantastic. Not enough people memorize great lines of literature.

A: Well, that’s the other tragedy. When I was a young lawyer, you could hear lawyers speak, and closing arguments were, compared to what you hear today, models of oratory and eloquence. Now, unfortunately—partially because of the change in the culture, which would make excessive quoting or formality stilted and unpersuasive, but also partially because we don’t have as many trials and the kind of practice that we should—you see a failure to have an appreciation for the language, which is, after all, one of the most beautiful in the world.


Q: Over the course of your career, have the kinds of cases that come to you shifted? If so, does it represent a change in the larger culture?

A: You know what I’ve noticed? The mentality that you used to see only in drug cases is the same mentality that you see in many white-collar cases.


Q: Meaning?

A: Meaning that at some point, the people who do business in this country adopted the ethic of gangsters. Except that the drug dealers are far more honest and straightforward.


Q: If you could give one piece of advice to a young trial lawyer about trial technique, what would it be?

A: It would be: practice. Go to trial advocacy programs. Practice, practice, practice. I would add this second admonition: Watch other lawyers, go to court and steal. If you see something nice, steal. If you read some quote in the newspaper that you like, steal. With respect to trial practice, there is no copyright law.


This interview has been edited and condensed.

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