An Interview with Aaron Fenton

Aaron Fenton is a sixth-year litigation associate at Mintz, Levin, Cohn, Ferris, Glovsky and Popeo, PC in the Boston office. He specializes in delivering practical solutions for clients facing complex issues such as insurance coverage, business disputes, and real estate matters. A graduate of Harvard Law School and former member of the Board of Directors for the Harvard Business Law Review, Aaron combines his finance background with his litigation expertise to provide high-profile clients with strategic advice on critical challenges.

From Studying Business to Practicing Insurance Litigation

With a background in business, Aaron initially thought he might gravitate toward transactional work. However, like many emerging associates, he wasn’t entirely sure what path he wanted to pursue long-term. While some law students have a strong sense of the kind of lawyer they want to become, Aaron pointed out that “you truly don’t know what you’re getting into until you start practicing.”

At Mintz Boston, summer associates are encouraged to explore work that sparks their interest, and Aaron took full advantage of this. Reflecting on his summer experience, Aaron shared, “I realized after the summer that I hadn’t really done any corporate work… everything that interested me was in litigation.” Once he recognized this, the decision became clear — litigation was the right fit. Since making that choice, Aaron hasn’t looked back.

Litigation at Mintz

When asked if litigation work matched his expectations, Aaron shared, “all that you know when you start is what you see on TV,” noting that trials are rare, if they happen at all. He explained that much of the work revolves around planning and what he described as the “adjacent to the adjacent to trial work,” which he found particularly rewarding. Aaron enjoyed immersing himself in the process, carefully strategizing to achieve the best possible outcomes if a case ever proceeded to litigation.

Aaron also quickly realized that litigation isn’t as combative as it might appear to outsiders—or even to the clients involved. “People tend to think there’s some huge gap between them and the other party, when there usually isn’t.” He takes pride in helping clients recognize how aligned their positions often are, which naturally leads most of his files to settle.

Aaron firmly believes that very few cases truly need to go to court. Instead, he remains optimistic about finding middle ground—a resolution that leaves both parties satisfied.

Specializing in Insurance

At Mintz, associates have the chance to explore work across different practice groups, and in the beginning, much of that work is similar. For Aaron, it wasn’t about a specific passion for insurance but rather an awareness that “I recognized that there is a need for this at the firm, and insurance was such a complicated field that there was lots for me to learn.” His thoughtful mindset allowed him to identify the opportunity, and he was drawn to the complexity of the work and the valuable learning experiences it offered.

Early on in his insurance work, since there weren’t many litigators specializing in insurance, Aaron often found himself working in small teams, frequently consisting of just himself and a partner. “I enjoyed the small-team work. You are kind of forced to take on extra responsibility when there are only two people on a case… it’s either you or the partner, and the partner is the busier of the two.” The nature of these teams gave Aaron significant responsibility early on, leading to growth opportunities he might not have otherwise encountered.

With insurance as his primary practice area, Aaron found that his enjoyment of small-team dynamics and his success in such settings opened the door to unique cases. One of his favorites from his time at Mintz involved a dispute over whether a man owned a lighthouse or not. What he found rewarding was tackling the problem by asking, “how can we take on an issue that doesn’t necessarily involve a lot of money, but is extremely important to someone, and defend that principle in the cheapest and most effective way possible?”

Aaron’s preference for small-team collaboration has shaped a career marked by variety and meaningful problem-solving. Whether he is representing a hedge fund manager navigating financial complexities or defending a lighthouse owner’s claim to title, Aaron thrives on playing an integral role in achieving practical and impactful solutions for his clients.

The Ebbs and Flows of Litigation

Sometimes, you’ll have a case where the facts or the law just aren’t on your side. When asked about this, Aaron emphasized the importance of managing client expectations: “At some point, one side is going to be forced to realize that they’re just not on the right side, and it is my job to navigate that process as best as I can.” Reflecting on his earlier years as an associate, Aaron recalled moments when he found himself drafting documents or handling files that didn’t always feel immediately impactful. To him, this is simply part of the job. He believes it’s essential to stay objective about your work and recognize your role as a vessel for pursuing your client’s needs.

When asked about managing the fast-paced lifestyle of a big law associate, Aaron was candid about the challenges. He described the demands as being what many would expect: long hours, working most weekends, always having your phone nearby. However, he pointed out that finding balance is possible, describing it as “an art form.” According to Aaron, “the most important thing is the people you work with and how you work with them.” His deliberate approach has led him to gravitate toward partners with whom he works well, which he believes significantly improves the day-to-day experience. “You’re not going to get along with everyone,” Aaron noted. “The key is to try and maneuver as much of your work as possible to the people that complement your work.” For Aaron, this involves understanding both his strengths and weaknesses and seeking out colleagues who can align with his tendencies and help him thrive.

Aaron’s well-being has also been supported by Mintz’s approach to work assignments. He values the firm’s awareness of individual dynamics and finds their system surprisingly personalized. “When the firm does assign me work, I know they’re going to assign me work with people that they know I work well with.” This thoughtful structure has played a significant role in helping Aaron manage the demands of his career while maintaining a sense of fulfillment.

Where is the Profession Going?

Aaron doesn’t believe AI will significantly impact the legal profession anytime soon—particularly not in litigation. So far, he noted, AI has had no effect on his day-to-day work. “Out of all of my friends, I feel like I’m the only one who doesn’t use AI on a regular basis,” he remarked. Aaron attributes this to a few key factors. First, law is inherently a human profession, deeply rooted in fact-specific, non-standardized scenarios. Second, and most importantly for litigation, is how crucial it is to be thorough. “Even if the AI model gives me a research answer, I still have to do my own research—how else am I going to know what I’m talking about?” He stressed the necessity of justifying your reasoning, internalizing the work, and tailoring every task to fit the specific needs of a client. “If anything,” Aaron added, “AI will help mitigate some of the most standardized work for junior associates and help lawyers devote more time to the important issues.”

Aaron’s experiences and success in big law underscore the critical importance of human relationships in the legal profession. Internally, he emphasizes the value of working intentionally with those who complement your strengths. Externally, he appreciates how personal legal issues can be, framing his work as an opportunity to bring people closer together. “It is important to get the clients to realize how close they should be. People tend to think there’s some huge gap between them and the other party, when there usually isn’t,” he explained. For Aaron, the essence of law lies in fostering connection and understanding—something he doesn’t see changing anytime soon.

With a deliberate mindset and a clear understanding of his strengths and limitations, Aaron demonstrates how to successfully navigate this demanding profession while making a meaningful difference in people’s lives.