The numbers just didn’t add up for Louis A. Di Filippo. After the Raleigh native earned his undergraduate degree in economics from NC State University, he calculated that a career in business and finance was not the correct answer. While the field made logical sense on paper, it didn’t ignite his passion. His curiosity for justice began with a paper he wrote during his undergraduate studies on the intersection of law and morality.
That assignment opened his eyes to the dynamic and human aspects of the legal system—a place where logic met ethics and he could make a meaningful impact. Inspired, Di Filippo pivoted from numbers to narratives, leaving the world of finance behind to pursue a law degree. He went on to earn his Juris Doctor from the University of Baltimore School of Law, graduating summa cum laude.
Under Pressure
In a whirlwind few weeks, Di Filippo graduated law school, packed up his life and moved to Greensboro, NC. His wife gave birth to their first child just three weeks before Di Filippo sat for the bar exam. For most, such a combination of life changes might feel overwhelming, but Di Filippo thrives under pressure. As he settles into this new chapter, Di Filippo is learning to balance the demands of practicing law, being a first-time father, and supporting his wife as she pursues her dream – a career in country music.
Di Filippo grew up in Raleigh, where he excelled in soccer from an early age. His impressive skills on the field earned him opportunities to pursue a collegiate soccer career. Unfortunately, a series of ACL injuries sidelined those dreams. This hardship taught him resilience and adaptability—lessons that would later serve him well in the legal profession.
Di Filippo joined Greensboro-based Ward Black Law last year to practice personal injury, workers’ compensation and mass torts. And as it turned out, his economics degree came in handy. “My background in economics helps with valuations,” said Di Filippo. “It’s making that determination of trying to quantify how much someone being unable to cook or garden anymore is worth. How do you put a dollar amount on that?”
Both Sides of the ‘v’
Di Filippo worked on both sides of the civil litigation equation in Baltimore. He practiced with a personal injury firm and then with an insurance defense firm handling personal injury and workers’ comp cases.
“I believe my experience serving clients on both sides of the ‘v’ equips me with knowledge of how to succeed for my clients and how the defense will operate. It’s always good to know how the other side is thinking when you’re trying to build a case. What facts are they going to latch onto? What facts will make opposing clients push back on settlement?” explained Di Filippo.
“I can tell clients where the fights will be, where you need to bolster your case, and where to compromise. I also know how to set expectations for the client by informing them of the good things in our case and the bad things as well.”
Despite the us versus them nature of litigation, Di Filippo said building rapport with the defense side is crucial. “If you don’t give them any breaks, when you inevitably need a favor or some help from the other side, they’re not going to give it to you.”
Building a Network
With the move back to North Carolina, Di Filippo is looking to build a network with local lawyers as a 2025 NCAJ Next class member. “It seems like an excellent opportunity to build leadership skills and to learn more about the behind-the-scenes aspects of working in the practice.”
The post Louis A. Di Filippo: Both Sides of the Equation appeared first on Attorney at Law Magazine.
