The following is an excerpt from Practice Perspectives: Vault's Guide to Legal Practice Areas.
Roxana (Roxy) Guidero is counsel at Wilkinson Stekloff. She has represented corporate clients and individuals in an array of industries and specialties, including entertainment and media, sports, antitrust and competition, product liability, and white collar crime. With a wide breadth of experience across the spectrum of trial strategy and preparation, Roxy has helped her clients navigate some of their most challenging and complex legal issues in courts from coast to coast and provided strategic counseling to international clients. Committed to equal justice and legal access for all, Roxy maintains an active pro bono practice. Roxy received the Los Angeles Center for Law & Justice’s Pro Bono Partner of the Year award following her work as lead trial counsel for a domestic violence survivor. She also served as a pro bono prosecutor with the Redondo Beach City Attorney’s Office, successfully trying multiple jury trials. Roxy is a lecturer in law at the University of Southern California Gould School of Law, teaching courses on contracts and antitrust.
Deon McCray is an associate at Wilkinson Stekloff. Before joining the firm, Deon was a law clerk to Judge Richard M. Gergel of the U.S. District Court for the District of South Carolina. Deon attended Georgetown University Law Center, where he received the Dean William M. Treanor Achievement Award for outstanding leadership. Deon was also named Chapter Leader of the Year for his service as president of the Black Law Students Association. During law school, Deon was an articles editor for The Georgetown Law Journal. He conducted research under Professors David Vladeck and Paul Butler. Deon interned for Commissioner Rebecca Kelly Slaughter of the FTC. Deon was also a member of the Civil Litigation Clinic.
Describe your practice area and what it entails.
Deon: We are a trial litigation boutique that can take any case to trial. Our attorneys have tried more than 200 cases, including over 20 trials since the firm opened. While we take cases at every stage of litigation, we are often hired to represent clients as cases are ramping up for trial. Our job is to focus on taking what is often a very broad record and simplify it into a compelling, persuasive narrative.
Roxy: We are a litigation boutique with a particular focus on trial practice. While we handle cases in a variety of stages, we do so with an eye toward success should the case proceed to trial. While many lawyers view trial as a last resort, we are thinking about our presentation to the jury from the moment a case first comes to the firm, which is sometimes before a complaint is even filed. We develop our trial themes early and use them to guide our decision-making at every stage; we do everything, from depositions to document discovery to the briefing of dispositive motions, with an eye toward our ultimate trial strategy. We strive to think long term and make decisions that will make our case come alive for the jury or judge. We also focus very strongly on diversity in the firm as it is our goal that our attorneys be reflective of the juries to whom we are presenting.
What types of clients do you represent?
Deon: The firm represents a wide variety of clients including large companies (Altria, Bayer, Microsoft, Glenmark, 3M, Cargill, Medtronic, Plaid, Allergan, and Georgia Pacific), sports associations (the NFL and NCAA), criminal defendants, and pro bono clients. The pro bono cases are some of the most rewarding, and Chambers & Partners has recognized the firm as having one of the two best pro bono programs of all law firms in the country, large or small.
Roxy: I have represented clients across industries from entertainment and media to oil and gas and from sports to pharmaceuticals. I am currently representing Visa Inc. against claims by the DOJ that Visa is monopolizing the debit card market. I am also representing ExxonMobil in climate litigation across the country. Recently, I was part of the team that successfully represented the NFL and its 32 member clubs in a class action brought by subscribers of NFL Sunday Ticket in the Central District of California and secured judgment as a matter of law for the NFL on all claims following a jury trial. Our clients and their legal challenges are wide-ranging and present a lot of great opportunities for our legal team.
What types of cases/deals do you work on?
Deon: Like all attorneys at our firm, we work on cases headed toward trial. In terms of subject matter, there is no single type of case on which we work. Over the past several years we have had antitrust, class action, criminal, products liability, and sports-related trials. Everybody at the firm floats between these areas and is exposed to all aspects of trial litigation.
Roxy: I’ve worked on a variety of cases, including merger investigations, criminal and civil antitrust lawsuits, breach of contract, copyright infringement, product liability, white collar crime, and tort matters.
How did you choose this practice area?
Deon: I discovered my passion for trial work during my district court clerkship. Working in a trial court was an incredible experience. The motion practice, the attorneys, and even the courtroom drama drew me in. I also admired the judge for whom I clerked, who was a trial attorney before joining the bench. His war stories and insights into trial strategy were inspiring and left a lasting impression on me. Trial work offers an endless variety of challenges and opportunities to grow, which keeps me energized and excited about my career.
Roxy: I did a lot of mock trial before starting my law practice—all the way back to high school. I enjoyed it so much that I thought, “If I am willing to volunteer so much of my time to this activity, maybe I should make it into a career!” That interest continued through law school and my federal clerkship, where I knew I wanted to focus my practice on litigation and oral advocacy.
What is a “typical” day like and/or what are some common tasks you perform?
Deon: My day always starts with an Americano—but beyond that, there is rarely a typical day. Every day brings new challenges and opportunities. For example, in a trademark case our firm handled for Plaid, the judge ordered supplemental briefing after summary judgment. We pivoted to meet the new briefing schedule and poured ourselves into the task. While not every day involves a surprise like that, the unpredictable nature of trial work—such as responding to a flurry of motions from opposing counsel—is a constant. It is this variety and intensity that make the work so rewarding.
Roxy: The best part of the job is that there is no such thing as a “typical” day. Some days involve a lot of strategy discussions, including many calls and meetings. Some days involve focusing on one specific legal issue and researching it or briefing it. And some days—the best days, I would say—you’re prepping
[space]for or are at trial where you can spend a lot of time with your witnesses and juggle a lot of tasks, making the long days fly by.
What training, classes, experience, or skills development would you recommend to someone who wishes to enter your practice area?
Deon: A trial lawyer’s ultimate audience is the jury, and juries value authenticity. They can sense when someone is not genuine, so the best advice I can give is to be yourself and connect with people on a human level. Beyond that, there is no single path to becoming a trial lawyer—many roads lead to Rome. My district court clerkship inspired me to pursue this career, but incredible trial lawyers like Beth Wilkinson prove that clerkships are not a prerequisite. What truly matters is having a strong interest in the work and the work ethic to master it.
Roxy: Any chance to get into the courtroom—whether it is to observe or in a speaking role—is an opportunity to learn more and absorb new skills as a litigator. Pro bono work is also extremely valuable for getting opportunities, especially for more-junior lawyers. I would suggest finding a cause that you are passionate about and figuring out ways to partner with com- munity advocates to get courtroom opportunities in that area.
What do you like best about your practice area?
Deon: What I like best about being a trial lawyer is having the opportunity to do it at Wilkinson Stekloff. Our named partners are still in their prime, leading by example and setting the standard. Beyond that, what makes trial work so exciting is the creativity it demands. There is no single practice area for a trial lawyer—we tackle cases across a wide range of subjects. Every trial is different: the judge, opposing counsel, subject matter, and client all change.
Roxy: The variety is the best part of the job. Each new case provides an opportunity to learn about a new industry and client and deep dive into their world for a bit. Our clients present interesting legal and business challenges, and it’s a privilege to work alongside them to address these issues. Then, taking this knowledge and breaking it down for the jury in a cohesive presentation poses intellectual and creative questions that challenge us to think outside of the box. There is nothing more rewarding in the practice of law, in my opinion, than seeing months of hard work come together at trial.
What are some typical tasks that a junior lawyer would perform in this practice area?
Deon: As a junior lawyer, I can confidently say the work is as substantive as it gets. In my first few months at the firm, I drafted portions of summary judgment motions, co-led the development of a slide deck for a jury exercise, crafted the theory behind and drafted a pre-trial motion, and handled ser- vice to the court and opposing counsel. Trial work at this firm offers junior attorneys the chance to dive right into meaningful, high-level tasks.
Roxy: Our juniors are part of critical strategy meetings—both internally and with our clients. They always have a seat at the table during witness preps. And they get to author briefs and trial outlines from the get-go. We think that better ideas flourish and our clients are best served when everyone has a voice and shares their ideas. The partners say they founded this firm to train the next generation of trial lawyers. And that is evident in the experience that our associates get.
What kinds of experience can summer associates gain at this practice area at your firm?
Deon: In my last case, two summer associates were staffed as integral members of the team and treated like junior associates. Law students come to Wilkinson Stekloff because they are passionate about trial work, and we make sure they get hands-on experience. A summer associate might attend a trial, participate in a jury exercise, or observe depositions and hearings. They also contribute to drafting motions, conducting legal research, cite-checking, and managing the essential nuts and bolts of litigation. It is a true immersion in trial practice, offering a clear glimpse into life as a junior attorney at the firm.
Roxy: Summer associates are treated as regular associates and brought into matters as if they’ve always been at the firm. Many of our summer associates have become integral members of our trial teams with the same opportunities as junior associates. In our NFL trial, which coincided with the summer program, we had a summer associate at the trial site the entire time. He participated in witness preps and strategy meetings, drafted trial outlines, and worked on the opening and closing arguments. And, of course, he also got opportunities to observe the trial and be in the courtroom.
How is practicing litigation in a boutique different from practicing in a large law firm?
Deon: At a boutique, the work feels more impactful, the stakes are higher, and the responsibility comes earlier. Having worked as a junior lawyer at a large firm, as a judicial law clerk, and now at a boutique, I see the boutique experience as much closer to clerking. Like clerking, boutiques place a premium on substance. Junior lawyers are deeply involved in meaningful, high-stakes matters and are trusted to contribute significantly. At a large firm, you are often part of a much bigger machine, handling smaller pieces of massive cases.
Roxy: Access and opportunities. A boutique firm allows you to feel really plugged in—both in our cases and in the firm community. There is never an unfamiliar face walking down the halls or on our case teams. Associates feel comfortable participating in meetings and contributing to case strategy, developing their skills early on. A smaller firm also allows us to really recognize talent, so associates can get opportunities as soon as they demonstrate that they are ready for them. And at our firm, you don’t have to sacrifice working with large clients that have interesting legal issues. You can have a high-caliber practice comparable to the best large law firms, while getting the environment of a smaller boutique firm.