This is the fourth in our occasional series of interviews with historic figures, focusing on their views on appellate advocacy. Earlier entries in the series include conversations with the Chinese general and strategist Sun Tzu, the Roman consul and orator Cicero, and Nobel laureate Ernest Hemingway.

While modern popular culture remembers Giacomo Casanova only as a libertine, he was actually a Renaissance man of extraordinary talent and accomplishment. In addition to his celebrated and lengthy memoirs, published after his death in 1798, he also authored a book on the history of Poland; several scientific and mathematical papers; and numerous essays, literary criticisms, and works of belles lettres. He was acquainted with numerous illustrious figures of his day, including Voltaire, Benjamin Franklin, Russian Empress Catherine the Great, Rousseau, and Prussian King Frederick the Great.

Over the course of his life, Casanova engaged in a variety of pursuits, besides women and writing. At times, he worked as an engineer, a factory manager, a trustee of the French state lottery, a concert violinist, a spy, and even – –

* * *

A lawyer? You were a lawyer?

Is that so hard to believe?

Well, no one these days ever thinks of you as a lawyer, or anything so mundane as that. Nowadays, everyone knows you as . . . as a . . .

I know what they think. Even in my day, historians tended to emphasize one aspect of a man’s character, and left all the others in the shadows, making the subject seem unnaturally one-dimensional. It takes a great historian to portray an entire man.

Has anyone ever written such a multidimensional book about you?

Heaven knows, I tried. I labored on the manuscript for Histoire de ma vie – you know it as History of My Life – but after I reached a certain point, the task simply became too painful; the memories too sad. I never really finished it.

So, did you hang out a shingle? Maybe take a few divorce cases, and console a few (heh, heh) jilted wives?

Always a comedian. Whenever they want to interview me, they always send a comedian.

You’re right; I’m sorry. Let’s go back to the issue of your legal career.

I wouldn’t exactly say I had a legal career. I was trained in the law, and received a doctorate in civil and canon law when I was 17 years old. Back then, I had my heart set on a career within the Catholic Church –

You’re kidding.

No, I decidedly am not kidding. It will probably come as no surprise to your ever-prurient mind that I was kicked out of the seminary. Choose your next comment carefully.

. . . Okay . . . So if you never really practiced law, I assume you didn’t handle any appeals.

You would not call me an appellate attorney, no.

So what do you have to say for our readers, who want to know about appellate practice and procedure? What can you tell them about how to be a better appellate lawyer?

Well, I can certainly speak authoritatively about persuasion –

[Interrupting] I’ll just bet you can.

Look, I’m not blind to the fact that history ignores my real achievements and brands me a single-minded womanizer. But even if the history books were right, I could still teach your readers a thing or two about persuasion. What do you think seduction is, after all?

I see what you mean. But surely the “skills” you employed in talking your way into a lady’s boudoir will not help in an appellate court, right?

In a sense, you’re right; I certainly do not advocate whispering sweet nothings or composing a sonnet for the benefit of an appellate jurist. But I will say that some of those skills can be translated into the appellate context.

I have to admit, I’m skeptical. But you have been kind to offer your time and advice, and I have probably been something less than gracious with you just now, so I’ll be very interested to hear some of your ideas on this subject.

Well, that’s one of the secrets right there: Listening. Being willing to listen to my lovers, instead of constantly battering them with my own words, has proven to be an enormously effective approach. Your audience can apply the same secret at an appellate lectern by giving careful attention to a question from the court.

To ensure that you understand the question before answering it?

That’s the most important reason, yes. But on another level, every person derives a certain private satisfaction when it is clear that his audience has understood him fully. One of your era’s philosophers, Stephen Covey, certainly recognized this when he urged those in search of greater effectiveness to “seek first to understand, then to be understood.”

So you’re saying that one of the keys of persuasion is to listen?

Exactly. Of course, you must comprehend what you hear. For example, I always paid attention when one of my lovers admired a particular flower. The next time I saw her, I would ensure that a bouquet of that flower preceded my arrival by half an hour.

You had me with you until you mentioned the flowers; now I’m confused. How does something like that translate into the appellate context?

It’s simple; you listen for what your justices like, in a brief or in your oral argument, and then you give it to them.

And I take it that’s something other than sweet nothings.

That’s one part of seduction that does not translate into your court system.

You suggest listening to appellate jurists to get an idea of what they like. When do they announce such things? And how do our readers get an invitation to hear them?

Well, they very rarely step up to a microphone and list the characteristics that charm them. But sometimes they do; appellate jurists are not hermits, and they occasionally address bar associations. Overwhelmingly the topic of those talks is how to do a better job of appellate persuasion. Beyond that, you can read their advice. Sometimes that advice is explicit, such as an article written for a journal; there are lots of those. Other times, you can read between the lines of their judicial opinions, when they point out what they don’t like, and figure out what they do like.

Such as?

Clarity, for one thing. There is no reason to say something obliquely in your brief, when you can say it clearly. That’s readily discernable from some of the court’s written opinions, for example, when they reject an argument as having only implicitly been raised.

Let’s talk about oral argument. What sort of style do you recommend for the advocate who wants to be as persuasive as a Casanova?

Certainly not the public image you have of the language of seduction; that has no place in an appellate court. Fundamentally, there is one thing that these two types of communications share: They’re interesting.

One of the keys to effective persuasion is to be interesting?

Absolutely! But it has to be within the proper context. For example, I was a student of medicine as well as of law. I could talk for hours about medicine, and with considerable authority. But can you imagine my trying to coax a lady with such talk?

No; not unless you’re trying to seduce Florence Nightingale . . .

You should be ashamed of yourself. Seduce an angel of mercy?

It was just a –

I understand exactly what it was. But remember, if in an appellate context, you write a brief that not only addresses the points you need to cover, but is also interesting to read, you will be well ahead of your opponent in the persuasion game. Every human prefers to read or listen to an argument that is interesting rather than dull. The same goes for my paramours; if I had ignored this simple truth, I never would have been able to . . . well, let’s just say I would have been remembered very differently.

How long should an appellate argument, either oral or written, be, to maximize its persuasive effect?

Shorter is better. Never use an epic poem to express what can be said in a couplet. When composing an appellate sonnet, it is decidedly unpersuasive to bludgeon the court with iterated and reiterated arguments, or with what the lawyers of your day call “string cites.”

Now you’re talking like a lawyer.

No, that applies with equal vigor to amorous persuasion. If I go on and on in praise of a given lady’s beauty, sooner or later she’s going to perceive that I’m desperate. An appellate court will start to reach the same conclusion if all you do is repeat your principal argument again and again, perhaps tripling the length of your brief. Consider that the next time you’re nervously comparing your brief with the page limits in your rules of court.

What’s the most persuasive way to answer a question from the court during oral argument?

Ah; this goes back to the very first thing we discussed, about giving your lover, or your judge, what she wants.

Okay; what does she want?

An answer, of course. Preferably a straight one. It is painful to watch some oral arguments, where the court asks a pointed question and gets an answer that is evasive or rambling.

Sometimes the lawyer is so afraid of conceding a point that he will stake out a logically indefensible position, or wholly separate himself from the factual record. On the other hand, to be optimally persuasive, you should give the court a direct, straight answer, every time. If you need to explain or qualify it afterwards, that’s fine; but the answer should always precede the explanation.

Have you encountered some appellate oral arguments in which the lawyer goes to great lengths to praise the court, at every opportunity?

Yes; your generation has a term for that. It’s called “kissing up to the bench,” and it is decidedly unpersuasive. It might have worked in my day, back in the Eighteenth Century, but only when addressing royalty; never a judge.

That’s interesting; did it work with royalty?

You bet it did. In the Nineteenth Century, England’s Queen Victoria was asked to describe the difference between Prime Ministers Benjamin Disraeli (whom she greatly admired) and William E. Gladstone. She replied, “After half an hour with Mr. Gladstone, I am convinced that he is the most interesting person in the world. After half an hour with Mr. Disraeli, I am convinced that I am the most interesting person in the world.”

You make Disraeli sound like such a sycophant.

Well, maybe in a sense he was. He himself once wrote, “Everyone likes flattery; and when you come to Royalty you should lay it on with a trowel.” The point is that this does not work on appellate jurists. So when you get a query from the court, you should resist the urge to say, “Your Honor, that’s an excellent question.” You’re likely to hear in response, “Thanks, counsel; now how ’bout an answer?”

This has been a very enlightening chat, much more so than I had thought when we got started. There’s just one other thing. I figure I may never have this opportunity again, so I’d like your advice. I don’t suppose you could give me a few pointers, you know, on how to impress the ladies? Surely there is at least one great secret to seduction that you could pass on.

Actually, there is one ultimate secret; something that is guaranteed to turn even the most cold-hearted, resistant subject into a more-than-willing lover.

There is?

Yes, but I have an inflexible rule: I only teach it to one person in each generation. And George Clooney got here before you did.