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David Borden, a former justice on the Connecticut Supreme Court, and now a colleague on the Connecticut Appellate Court, likes to tell the following story. Borden was fond of asking lengthy � and sometimes, convoluted � hypotheticals to tease out a lawyer’s argument. At the beginning of one argument, a young, rather shy lawyer stood up to speak. Borden immediately interrupted to ask a hypothetical question. The question went on and on, positing a wide variety of facts and circumstances having nothing to do with the case at hand. In fact, Borden concedes, even he was losing track of all the issues he had loaded into the question. The young lawyer stood there for minutes as the hypothetical went on and on. Finally, when Borden had concluded, the lawyer paused and sheepishly asked: “Your Honor, would you remind repeating that question?” Not to be outdone, Borden replied, tongue in cheek: “I’m sorry, you’re out of time.” The bench, and the courtroom, erupted in laughter. However, as anyone who has been on the receiving end knows, hypotheticals are no laughing matter. They can be nerve-racking. They test the mental dexterity of even the best prepared, most experienced and talented advocates. A few years ago, I spoke with Mike McCurry, President Bill Clinton’s former press secretary, about answering hypothetical questions put to him by members of the White House press corps. He told me it was his policy never to answer hypotheticals. “Hypotheticals are very dangerous because they take you into unchartered territory,” he told me. In this column, I will discuss hypothetical questions � why they are asked, and how to effectively deal with them. (My thanks to Jessica Ragosta, a student in a class I taught last year at the University of Connecticut School of Law, for sharing with me her paper on effectively responding to hypothetical questions.) An interesting question on hypothetical questions Why do judges ask hypothetical questions? As noted by E. Barrett Prettyman in “The Supreme Court’s Use of Hypothetical Questions at Oral Argument,” 33 Cath. U. L. Rev. 555, 556 (1983-84), there are several reasons. One may be that during prolonged argument, judges simply want to vary the routine. “A more generous view is that the court is testing the outer reaches both of what the advocate is asking it to declare and of what the Court may, in fact, have to decide.” Some hypotheticals, he suggests, are not really addressed to the advocate, but are for the benefit of fellow judges. ” ‘Do you really want to go as far as I think you are heading, even if you have the votes?’ “ Understanding that hypothetical questions may be asked for different reasons, from the advocate’s standpoint, two are paramount. First, inquiring judges frequently want to test the outer boundaries of an argument, see how far it reaches, and force a concession. Second, inquiring judges want to evaluate the possible impact on future cases of accepting the position being advocated. The skilled advocate, therefore, should look upon the hypothetical question as an opportunity to explain to the court the parameters of what is being sought and how it would affect future decisions. It is difficult to talk in the abstract because each situation is different. And, of course, it is impossible to anticipate precisely what kind of hypotheticals will be thrown at you during an oral argument. Some hypotheticals are long and convoluted; others are short and to the point. In any event, counsel’s antennae should go up � way up � when a judge begins a questions with the words “Assume,” “What if,” or “Suppose that.” Notwithstanding that each situation is different, here are some common sense suggestions that may be of assistance in handling hypotheticals. 1.) Preparation is everything. As with advocacy generally, it is impossible to be too prepared. If you have started to think about what hypothetical questions the court might ask you as you rise to speak, it is too late. You must know the facts of the case, and the law, better than your adversary. In advance of argument, you should discuss your case with colleagues, flesh out the weaknesses in your position, and engage in practice arguments. You should know the inner and outer boundaries of your argument and understand the implications � for other future cases � if your argument is accepted. Imagine what hypotheticals might be asked. Prior to argument, try to imagine what hypothetical questions you would ask if you were on the panel. 2.) When a judge asks you a hypothetical, listen carefully to the question you are being asked. The first rule of responding is simple but imperative. You should never respond to a hypothetical unless you understand precisely what is being asked. A casual response, or a quick reply in an effort to appear facile, can be disastrous. You could accidentally concede your case away or make an argument that will require embarrassing backpedaling later on. If you don’t understand a question, you should simply ask the judge to repeat it. 3.) Mentally isolate the distinguishing factors. Once you understand the question, to effectively provide an answer, it is important to mentally isolate the factors that distinguish it from the facts of your case. Only if you do this can you analyze what you are being asked, and persuasively respond, avoiding a damaging concession. 4.) Articulate clearly how your case differs from the hypothetical scenario being posited. This can be done in a number of ways. One way is to begin by agreeing with the premise underlying the hypothetical, but clearly distinguishing the issue for decision. In other words, use the hypothetical as a jumping off point for reinforcing the key factual, or legal distinctions, that apply to your case. This sounds something like this: “Your Honor, I fully agree that if my client had sandy brown hair, that would bolster the victim’s identification of him. But as the record clearly reflects, my client was, and remains, bald.” Or this: “But in that case, unlike this, there was uncontroverted evidence that the defendant spoke, and understood, English. In this case, the record is clear that my client speaks no English whatsoever.” Skillful handling of hypotheticals in action Let me now provide a concrete example of effectively responding to hypothetical questions. The case was Smith v. Daily Mail Publishing Co., 443 U.S. 97 (1979). Newspapers had published the name of a juvenile who had been charged with killing another youth in violation of a West Virginia statute protecting the identities of juvenile offenders. The papers had lawfully discovered the name of the alleged offender. The U.S. Supreme Court held in this case that the state could not punish the truthful publication of the juvenile’s name. Representing the respondent newspapers in this case, involving sensitive issues of prior restraint, was First Amendment expert Floyd Abrams. Here is a small, slightly edited excerpt of the argument demonstrating Abrams’ skill at responding to hypotheticals. Because space limitations prevent me from offering a longer excerpt, I urge interested readers to read the complete argument to appreciate the full flavor of the advocacy involved. “ Abrams: [The statute] is a prior restraint in our view because the essence of it � and the essence of the crime alleged here � is what you must seek written permission of the judge before you can print the name of the child. That in our view is what makes it a prior restraint. “ Question: Would it be a different situation if [an] exception were not provided in the statute? “ Abrams: Yes, it would, Mr. Justice Blackmun. It would not be a prior restraint in our view then; it would be a straight subsequent punishment, a criminal statute to be judges as you judge against First Amendment interests and First Amendment claims, criminal statutes which affect or directly implicate the rights of the press. “ Question: Mr. Abrams, I notice that you put, or appear to put, a good deal of weight on the fact that between 1960 and 1975, as we all know, there has been an enormous increase in juvenile crime and serious violent crime. Now suppose the statistics were the other way � suppose it showed that juvenile crime was going down. Would it make any difference to your constitutional point? “ Abrams: No, it would not, Mr. Chief Justice. I simply indicated that to indicate to you why the press might want to print that for information of the Court, but that is not the heart of our argument. “ Question: It is really irrelevant, isn’t it � “ Abrams: It is � “ Question: � whether crime is going up or going down? “ Abrams: It is irrelevant to the legal position of � “ Question: It is a constitutional question. “ Abrams: Yes, sir. Yes, sir, it is . . . . “ Question: Suppose, Mr. Abrams, there weren’t seven eyewitnesses, and that he was apprehended on some circumstantial evidence. Would that make any difference to your constitutional issue? “ Abrams: The constitutional issue, no . . . .The constitutional argument remains precisely the same, whether or not anybody knows about it in any particular case. It seems to us that this statute which punishes speech, which is in our view a prior restraint as well on speech and on the press, cannot pass muster.” Note the succinct, focused answers to the questions, followed by brief, persuasive embellishment. Note the clear sense of understanding the parameters of the claim being made, and the understanding of the perspective that the judges will bring to their analysis. Douglas S. Lavine is a judge on the Connecticut Appellate Court. He is the author of Cardinal Rules of Advocacy (NITA 2002) and Questions From the Bench (ABA Section of Litigation 2004).

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