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The following is an excerpt from Practice Perspectives: Vault's Guide to Legal Practice Areas.

Tacy F. Flint, Partner—Litigation

Tacy is an experienced appellate litigator. She authors briefs and critical motions in a variety of commercial and constitutional cases, and she has argued in state and federal courts across the country. She is skilled at pulling apart complex legal and factual topics so they can be woven together into the most compelling argument for her client. Tacy’s strong advocacy for her clients won her recognition in 2017 as one of 40 Attorneys Under Forty in Illinois by Chicago Daily Law Bulletin and as one of the 60 Most Influential Women Lawyers in Chicago by Crain’s Chicago Business. 

Tacy’s practice spans a wide range of legal issues, including antitrust law, ERISA, securities laws, intellectual property, federal jurisdiction, and the First Amendment. She maintains an active pro bono practice and has represented numerous clients in cases concerning immigration, education reform, and fair elections. She is also co-chair of recruiting for Sidley’s Chicago office and a member of the firm’s Committee on Retention and Promotion of Women. Prior to joining the firm, she served as a law clerk to Justice Stephen Breyer and Judge Richard Posner.

Describe your practice area and what it entails.

The key role of an appellate litigator is applying judgment to answer hard legal questions. Most often this happens in the writing and editing of briefs. When you’re writing a brief for a client appealing an adverse judgment, your job is to crystallize the entire case into one document that persuades three judges that the trial court got it wrong. Your first task is to choose which issues you’re going to present. This takes judgment: Which issues will let you make the most compelling arguments for getting the relief that is most important to your client? Which issues build on each other thematically so that the complete picture paints your side in the best possible light? Too many issues and you won’t have enough space to develop any single argument, plus you’ll lose credibility by suggesting that the lower court judge (who is, after all, a colleague of the panel you’re in front of) couldn’t get anything right. But you also don’t want to leave strong points on the table.

Once you land on the right set of issues, your next job is to cull through the record to put together a factual narrative that is both scrupulously accurate and right in line with the case law you’ll be relying on. With the substance in place, your next job is to choose the language that best expresses it. You need a tone that matches your substantive position plus some snappiness to keep the reader’s attention—and you want to use as few words as possible without losing accuracy or key points. Every step of the process demands judgment.

And there’s a lot more to an appellate practice than appellate brief-writing. Most appeals also involve oral argument, which requires a whole different set of judgments. And appellate lawyers routinely write and edit briefs and argue motions in lower courts, which involve related but distinct strategic judgments. Beyond briefs and arguments, appellate lawyers frequently weigh in on other legal questions: Is this regulation valid? Should we file a lawsuit? What are the legal risks if our organization takes X, Y, or Z step? Really, anything that involves thinking through hard legal questions fits within the practice of an appellate litigator.

What types of clients do you represent?

Because my practice does not focus on a particular subject matter, my clients are quite varied. Most are large corporations—including technology companies, financial services firms, insurance companies, and life sciences companies. I also represent a number of nonprofit associations and foundations, as well as individuals facing high-stakes personal or professional disputes. In my pro bono practice, I have represented individuals seeking asylum in the United States, criminal defendants, students seeking equal educational opportunities, groups working to promote fairness in legislative redistricting, and nonprofit organizations challenging improper restrictions on immigration.

What types of cases/deals do you work on?

One of the best features of my practice is that I get to work on all kinds of cases. For example, I’ve worked on a number of cases raising fascinating regulatory and statutory interpretation questions. I’m currently representing a nonprofit organization that provides services to immigrants, which is challenging a new rule promulgated by the Department of Homeland Security. Our briefs in the district court and on appeal deal with statutory interpretation, administrative law, standing, and the proper scope of an injunction—some of the most pressing legal issues out there.

I also work on a wide variety of business-related cases, involving intellectual property, contracts, antitrust, ERISA, securities laws, and the myriad other legal issues that businesses face. Each case involves its own educational phase, where I learn the facts and the law. Being new to something is often an asset: When you’re starting fresh, you can see which points prove important to someone coming to the question for the first time, as the judge will be.

How did you choose this practice area?

From early in law school, I liked legal analysis and writing. Then clerking on the court of appeals and the Supreme Court clinched my interest in appellate litigation. For one thing, the exposure I got in those two years to appellate argument was a terrific education. While nearly all of the lawyers litigating in the Supreme Court are top notch, on the court of appeals, you see a wider spectrum of quality, candor, and persuasiveness in legal argument. You can learn a lot from both excellent and dubious briefs. Having seen all that from the perspective of a clerk positioned me well to join the fray.

And spending two years around appellate courts and appellate arguments showed me how much I liked it. In those jobs, I loved getting to think through hard questions and then talk about the answers with the brilliant people I worked with in chambers. Now, that’s what I do at Sidley.

What is a typical day like and/or what are some common tasks you perform?

My three main tasks in any given day are reading, meeting, and writing. If I’m reading, it’s usually a brief that has been submitted by the other side, cases, or transcripts or documents that make up the record in our case. If I’m in a meeting, it’s with other lawyers or our client as we decide how we’re going to proceed. We toss ideas back and forth about what arguments look good or bad, what we think our brief should say, or what points warrant more emphasis or explanation at oral argument. And then I’m writing. Usually, I’m writing with the benefit of a first draft prepared by one or more associates, which is a real pleasure. Inevitably, they come up with points or unearth facts or authorities that I didn’t hit upon, and the product of our joint efforts is all the stronger.

What training, classes, experience, or skills development would you recommend to someone who wishes to enter your practice area?

The number-one experience is a clerkship. An appellate clerkship is ideal because it gives you exposure to a year’s worth of appellate briefs and oral arguments. You quickly see what you find persuasive, what questions you want appellate advocates to address, and what material is most useful to you as you’re working on the case. And you also see on a daily basis how your judge reacts to different arguments and styles.

What misconceptions exist about your practice area?

Many people think, not unreasonably, that appellate litigators do appellate litigation. That may be true for some appellate lawyers out there, but not me. At least half of my practice is in trial courts. I work with trial teams to write key trial briefs like preliminary injunction motions, dispositive motions, and Daubert motions; I work on jury instructions and post-trial motions; and I help with legal analyses and strategy questions that come up throughout the life of a case.

What are some typical tasks that a junior lawyer would perform in this practice area?

Junior lawyers working on appeals are usually writing the brief. Typically, the team will talk together about the general arguments we want the brief to make and the key points we want to emphasize. From that point forward, it’s the associate’s show. She handles the case law research, mines the record, ascertains the rules of the court we’re in, and writes it all up. My favorite is when, time permitting, one associate can handle the whole shebang, because that makes for the most cohesive overall document.

What kinds of experience can summer associates gain in this practice area at your firm?

I use summer associates on appeal teams as often as I can. In a few cases, when the timing and circumstances worked out well, I have asked a summer associate to write a complete brief. More commonly, I ask a summer associate to write a stand-alone section, which we insert into the larger brief. And because appellate briefs allow for in-depth treatment of key legal issues, an appeal team can really benefit from a summer associate’s deep dive into case law.

What is your routine for preparing for oral arguments?

I like to identify 10 or so questions that have been lingering in my mind about the case, and then I write out answers to those questions. Next, I read my written answers aloud. In case you haven’t read your own writing out loud recently, I can tell you that—like hearing your own voice—your own writing read aloud sounds clunky and awkward and never says quite what you want it to say. So it takes several tries and several rewrites before I get to a set of answers that I’m satisfied with. As you go through this process with all 10 questions, you’ll see yourself coming back to the crucial themes over and over, and now you will have written and spoken them aloud many times. These are the themes you want to hit when you answer the judges’ questions at argument. You make sure to answer the judge’s particular question, and use your thematic point—now firmly implanted in your mind—to demonstrate that that answer fits into and supports your view of the case.